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Talk:Aspirin/Archive 1

Initial comments
The systematic name for this is listed as 2-acetyloxybenzoic acid. Shouldn't that be 2-ethanoyloxybenzenecarboxylic acid? (Sorry if that sounds pedantic.)

I thought so as well, but PubChem and the CAS registry both say 2-acetyloxybenzoic acid. Bfesser 22:27, 17 February 2007 (UTC)

Small typographical correction: in the synthesis section, I changed 'acylated' to 'acetylated'. -- Kurtis (not registered)

COX is short for cycloxygenase enzyme which catalyses the production of prostaglandins, prostacyclines and thromboxanes from arachidonic acid. Aspirin inhibits this enzyme---bon

Could someone please check the pharmacology of aspirin described here... I thought COX was a type of prostaglandin... --Dweir

Nope, platelet cyclooxygenase is an enzyme that mediates the synthesis of prostaglandins (among other things) - I think there is a mistake though, in the platelet aggregation bit, in that it is thromboxane A2 (TXA2), also produced via a COX-mediated pathway, which is not a prostaglandin as stated, that increases platelet aggregation. Will do a bit more research and maybe edit the article re: effects on MI -- Alex.

I think they bought the Aspirin trademark back together with the American company named Bayer in 1994? The article sounds as if they currently don't have the trademark in the U.S..

 * They don't--no one does...it was declared generic in a 1921 federal court case, so there's nothing to buy--the mark has no commercial value in the US. Contrary to many stories adrift on the internet, this had nothing to do with the stripping of Bayer's assets during WWI, because the trademark was simply resold along with the rest, and then ruled generic a few years later because of public usage as a generic term.--postdlf

In Europe at least, the patent on the principle should have been expired; effectively other firms than bayer are already producing it. Does someone have better informations on the point?

 * I can't speak for other countries, but the patent in the US expired in 1917. However, "Aspirin" could have still been a viable trademark even with the patent in the public domain, if Bayer (and Sterling, the subsequent owner of the "Aspirin" mark) had better protected the brand name against use by competitors.--postdlf

128.193.88.189 - Please justify putting disclaimers on articles. It is a slippery slope. --snoyes 18:44 Feb 20, 2003 (UTC)

 * OK, I found a standard disclaimer on Wikipedia medicine standards - please use this in stead of any other text. --

snoyes 18:55 Feb 20, 2003 (UTC)

I prefer an article about acetylsalicylic acid and a redirection from aspirin, because  acetylsalicylic acid is the active agent and aspirin is only a commercial name ( imagine, what would happen if we include all the commercial names of  acetylsalicylic acid ). Applying the generalization principle I suggest include the information in the acetylsalicylic acid article with a reference to aspirin like the first  acetylsalicylic acid product.

 * I agree, aspirin is a common term for it, but it should be under acetysalicylic acid.70.49.36.110 23:30, 20 Apr 2005 (UTC)

I really don't think the last paragraph should be there. It's not well written, and seems to be totally separate from the general feel of the page. It really doesn't give any critical information and mentions several topics that are not explained. Use of acronyms for items not previously discussed and mentioning things still in the research phase are bad ideas for an encyclopedia also.

Aspirin is a BRAND. It has copyright.
It's a BAYER brand for acetylsalicylic acid.

It would be better to redirect aspirin to acetylsalicylic acid

--217.217.9.97 20:43, 31 Oct 2004 (UTC)

Brands are protected by trademarks, not copyright. Aspirin, furthermore, is a generic term in many countries, including the U.S., which means it does not function as a brand. The article explains this. Postdlf 01:18, 1 Nov 2004 (UTC)

Well, though Americans do not care much about other's properties, such as registered trademarks, this is an international encyclopedia and therefore to avoid complications the name of the drug should be used rather than the legally protected name. So main article to ASA and redirect there from Aspirin 84.129.215.116 18:20, 24 July 2006 (UTC)

 * As far as I can tell, looking at my British National Formulary, Aspirin is the International Nonproprietary Name (INN) and as per WikiProject Drugs/General/Naming of drug pages, is the name that should be used. David Ruben Talk 01:23, 25 July 2006 (UTC)

 * That seems pretty clear, and I agree, most people would be looking it up under Aspirin rather than 'acetylsalicylic acid'. An encyclopaedia such as Wikipedia is meant to explain the chemical background to readers who don't know much about it, they are not meant to arm themselves with prior foreknowledge before they come to Wikipedia. If I had never heard of ASA why would I want to rely on a Redirect from "Aspirin" and be confronted by a name which I would only undertand after reading the whole article. I am speaking as Wikipedian. Dieter Simon 21:28, 25 July 2006 (UTC)

 * Still, it is a registered trademark and a proprietary name to the Bayer AG and therefore has to carry a ® when used in common terms. Using the non-proprietary name acetylsalicylic acid is better, though, because this article should not only be about the original stuff from Bayer but about the drug which is also used in generics. 80.136.198.208 22:11, 20 February 2007 (UTC)

 * As noted above, the name was genericized in the 20s. Even if Wikipedia's manual of style (see WP:MOSTM) specified the use of ® and ™ on trademarks (it doesn't), the name is no longer a trademark anyway. Zetawoof(ζ) 22:41, 20 February 2007 (UTC)

 * Even though the name has been STOLEN in some countries, it makes no differences to the fact that it is a proprietary name owned by the Bayer company. The fact that in some countries people don't care about the rights of others shouldn't become the common way. Otherwise you could use chinese counterfeits to describe brand products. Even though the name is illegally used by many U.S. companies, it is still stolen. Wikipedia shouldn't contribute to that. Otherwise, what would you say when I started my own fast food restaurant calling it Burger King? 80.136.198.208 23:47, 20 February 2007 (UTC)
 * Bayer still maintains the trademark Aspirin here in Canada, and so I was a little surprised to find ASA (by which generics are known here) redirected to aspirin, when products still maintaining trademark already forward to their generic names (as Lipitor does). I went to see if I could find aspirin / ASA in the INN lists, I found these here but didn't see aspirin OR acetylsalicylic acid.  Could some one provide reference to the actual recommended (not proposed?) INN entry for ASA to clear this up?  From what I read in one of the INN documents, the purpose of the INN is so that NO party could claim ownership over the term... so wouldn't chosing a brand name still held in Canada defeat the purpose of HAVING an INN?  I acknowledge an above user had the British formulary in hand, and that I was rather tired when scanning those lists (gah!  scans!) but a direct link to the document would be perfect! - BalthCat 07:54, 18 June 2007 (UTC)

 * The word "aspirin" is recognized as a Bayer trademark by Germany and numerous other countries, but it treated as a generic drug description in the United States, the United Kingdom and France. Trademark rights were seized as an economic reparation under the treaty of Versailles, Article 297, Annex section 5. Use of the "aspirin" trademark in the United States was reportedly sold to Sterling Products by the Alien Property Commission in 1919 (see "Drug, Disincorporated," Time, July 10, 1933). Prior to that, however, Bayer had challenged United Drug of Massachusetts in a United States trademark infringement lawsuit, Bayer Co. v. United Drug Co., 272 F. 505, decided in 1921, mainly in favor of United Drug. Curiously, Bayer's standing to sue was not questioned by the district court decision for that case, but perhaps that reflects failure by the U.S. Congress ever to ratify the Treaty of Versailles. In any event, as of January, 2007, the Wikipedia article's discussion of "aspirin" as a trademark needs review. It claims that "[t]he right to use the aspirin trademark in the United States (along with all other Bayer trademarks) was purchased from the U.S. government by Sterling Drug in 1918." Not according to Time and not likely, since the Treaty of Versailles was not signed until 1919, and possibly not relevant, since the United States never ratified the Treaty. The decision in Bayer v. United Drug recognizes a right of United Drug to distribute bottles for retail sale containing up to 50 tablets labelled with "aspirin" as a generic word, but not to so label larger containers or to engage in wholesale trade using "aspirin" as a generic word. Nevertheless, forty years later containers of at least 1,000 tablets were being sold in the United States by Lit of New Jersey and by perhaps other manufacturers labeled with "aspirin" as a generic word. However, Bayer has not entirely given up in the U.S. It appealed a rejection of an attempt to trademark "aspirina" (meaning "aspirin" in Spanish), but it lost in the Court of Appeals, In Re Bayer Aktiengesellschaft, Ser. 78/212,751, May 24, 2007.

____________________

Made a few changes - removed "including US" for NPOV reasons, aspirin is still used to treat flu (just not in children) and removed the statement that "his reasoning was very much in error", as his reasoning is not actually stated! Dan100 23:29, Dec 17, 2004 (UTC)

But, but, but. . . I thought dextro-glucyloctose was an acetylmorphinol!! lol!

List of countries that have rejected Aspirin as a registered trademark
USA, Sudan, Australia, China, South Africa, Mongolia, New Zealand, Argentina, Indonesia, Angola, France, United Kingdom, Morocco, Mozambique, Cote d'Ivoireand Uganda.
 * It should also be noted in India and half of African countries, Bayer never registered the trademark. All the countries listed above are countries where Bayer initially owned the trade mark.

Added an image
I added a picture of pure crystals of acetylsalicylic acid under the 'history of discovery' section. I had extracted some from aspirin pills today (using acetone), with plans to hydrolyse it and then make oil of wintergreen with the resulting salicylic acid. I figured I'd take a picture of this first and add it to the Aspirin article.

Methylsalicylic acid
Can someone pharmaceutically qualified check the formula details in the box, such as those altered to "methylsalicylic acid", etc.? I wish people put a sign-on name to an edit. Dieter Simon 00:30, 16 October 2005 (UTC)

Action of salicylic acid?
There's something about the logic of the article that's a little hard to follow. The early sections imply that aspirin was originally discovered as a derivative of salicylic acid, which had somewhat the same pharmacological uses. Later on, though, it claims that aspirin works by acetylating COX:
 *  This happens because cyclooxygenase, an enzyme which participates in the production of prostaglandins and thromboxanes, is irreversibly inhibited when aspirin acetylates it.

Now, obviously salicylic acid doesn't acetylate anything; it has no acetyl group. So why would salicylic acid have the same effects? Please explain. --Trovatore 19:30, 30 November 2005 (UTC)

Answer better late than never: This is an example of scientific ideas changing with time. When aspirin was first commercialized by Bayer in 1899, nothing was known about the mechanism of any drug. Aspirin was considered just a less acidic form of salicylic acid, and assumed (then) to work by being hydrolyzed in vivo to salicylic acid which was supposed to be the real analgesic. The acetyl group was (then) considered just a blocking group to reduce the acidity in the stomach.

However the work of Vane in 1971 disproved this idea and showed that the essential action of aspirin is the acetylation of COX. This acetylation does of course produce salicylic acid as a secondary product, but its biological effect is minor compared to the inhibition of COX.

As for similar pharmacological uses, it is just a coincidence that both inhibition of COX and salicylic acid produce analgesic effects. And the inhibition of COX leads to other effects which salicylic acid does not, for example the anticoagulation effect which is helpful in preventing strokes. Dirac66 23:43, 20 September 2007 (UTC)

Boiling point/decomposition
To answer the question posed in an edit summary, a number of sources specify decomposition upon heating. Here's an example of an MSDS : Edgar181 01:07, 21 January 2006 (UTC)

Test for ASA
There was a standing request in the natural sciences portion of Requested_articles/Natural_Sciences. I dont know if this request was for analytical or in vitro testing, and I didnt think that it would be appropriate to add a new article on the subject. The request has been present for over a month,so I thought I try to fulfill it here. If you have suggestions on how to better handle this request, let me know. rmosler 10:08, 27 March 2006 (UTC)

Looking at all the information, I think I will reconsider combining the articles and just have a stand alone article on salicylate testing rmosler 10:46, 27 March 2006 (UTC)

SMILES
The current SMILES string used in this artice is. However, the article about this molucale representations says aromatic rings should be in lower case. Furthermore, I'm not really an expert, but I'd say renthesis ahould be used either in the label, the second 1, or in the acidic radical. That said, perhaps  is a better representation. jοτομικρόν (talk, email) 20:08, 25 April 2006 (UTC)
 * I updated the SMILES string to include information on aromaticity. It wasn't really wrong originally, but this way is a bit more precise. --Ed (Edgar181) 20:24, 25 April 2006 (UTC)

The name
"Aspirin" is not an official name of the molecule, it's just one of the drugs that contain acetylsalicylic acid. It's a serious abuse to use name of a product that contains a molecule as a name for the molecute, trademarks or not. Taw 16:40, 9 May 2006 (UTC)

 * Wrong. Aspirin = Acetyl salicylate. Paracetamol does not redirect to acetaminophen. Paul C 17:59, 9 May 2006 (UTC)

 * Do you know about at least one scientific source that call the molecule aspirin ? Taw 20:37, 30 May 2006 (UTC)

 * Goodman & Gilman's Pharmacological Basis of Therapeutics? Paul C 23:08, 30 May 2006 (UTC)

 * Oh well, I don't like having article about acetylsalicylic acid under aspirin, but if even medical sources abuse it this way, there may be little choice ;-) Taw 15:27, 1 June 2006 (UTC)

 * Calling the acetylsalicylic acid molecule aspirin is not abuse! You're just being pedantic.  It is commonplace in organic chemistry to refer to a molecule by a trivial name such as aspirin.  See for example ibuprofen, oseltamivir, cocaine etc.

 * Ben 16:45, 1 June 2006 (UTC).

 * I have never seen a box of anything saying it contained acetylsalicylic acid, they all say aspirin202.161.5.252 09:26, 22 May 2007 (UTC)
 * Come to Canada and buy some ASA! - BalthCat 07:58, 18 June 2007 (UTC)

 * The Merck Index lists it as aspirin. --Itub 08:03, 26 September 2007 (UTC)

Section called "Aspirin"
Is there any way to make sense of the section under the header "Aspirin"? From the text of the article one can't tell who or where "Sterling" came from. Also, shouldn't that portion of history under the header "Aspirin" be combined with the section entitled "Discovery". The two sections tend to overlap. 24.186.214.2 20:22, 7 June 2006 (UTC)
 * I might try a better introduction of Sterling Co. Someone took a senence from somewhere and didn't introduce the Sterling company properly.Gaviidae 11:15, 6 July 2006 (UTC)
 * update: I made a Sterling page but it sucks and needs work. Help.  Gaviidae 17:56, 9 July 2006 (UTC)

Aspirin and Cancer
Someone had a citation-less sentence about some recent article proclaiming aspirin's anti-colorectal cancer properties-- as I went to get the actual article, I found so much about aspirin and cancer out there that I made a whole new section, because it didn't seem to belong in the How It Works section anymore. I've sort-of listed the articles in chronological order. If anyone has other significant studies (ie, other parts of the body), please add them. I tried to find the actual studies rather than 3rd-party CNN/BCC-style accounts, so that readers can see the actual papers if they wanted more info. This seem a good idea or is there some Wiki-cancer-aspirin page out there that this should go into??Gaviidae 11:15, 6 July 2006 (UTC)

 * Thanks for information - the risks of NSAIDs (GI bleeds and incr heart disease) probably outweigh most of the benefits seen - particularly considering the high dosages looked at in some of these studies. Indeed I believe it was studies of COX-II use at preventing Colon cancer which highlighted the recent much reported risks of COX-II as causing heart disease & deaths. With attention now turned to the more conventional NDAIDs (Ibuprofen & Diclofenac), these too seem to have a previously underappreciated coronary risk in long-term usage. So even hinting at use of aspirin for cancer prevention in an "open" source such as wikipedia carries risks (I've admitted several patients in the past with acute gastric ulcer bleeds due entirely to self-medicated aspirin use for "heart protection" when there was no clinical need for them to have done so, fortunately none died). The effects and studies on aspirin on rates of cancer is fascinating though (both on what it reveals about the pathophysiology of cancers and approaches that might be taken to help prevent) - but for now this is purely research, speculation (of what the overall cost-benefit outcome might be), and not part of established medical advice/practice.
 * I've moved it down to the end of the general discussion on (established) use.
 * I don't think wikipedia is the place to discuss at length each single study (vs citing perhaps an official guideline that considers cost-benefits and cites its sources). I grant your prose is well written, but I would prefer in wikipedia to see a more succinct style that does not include in the main text the details of which journal and which team undertook a particular study - my personal feeling is that such information is best included by modifying in-line links to full footnote citations.
 * I wont for now have a go at compacting down the information you clearly so carefully sourced, as I think it would be useful to first see if other editors agree with your thought that such info might best be served in its own article to which 'Aspirin' then points. Rather than Aspirin effect on cancer, might not the more general NSAID effect on cancer be helpful, given that there has been well reported studies looking at COX-II use for colon cancer that created so much controversy ? David Ruben Talk 13:22, 6 July 2006 (UTC)

 * Thanks for the comments. I'm not sure how to provide citations to the ideas without citing the actual papers-- and I also mentioned the sizes of the populations (important because smaller study sizes don't weigh as much in my and many others' minds) and who was involved (women in these studies, mostly), and how they did them (for instance, some of these are simply asking people how much aspirin they take, and people are notoriously vague when asked about their habits-- thus I mentioned whether particular studies were questionaire-style or empirical (the actual studies say how correct they think the participants' answers were)). I also mentioned some of the researchers' reservations at the high doses used by some participants (2 aspirin a day, wow).  As much as I wanted to simply mention that there was research into aspirin and effects on various cancers, every time I tried to leave something out it became quite useless, or skewed the general NPOV in at least my feeling.
 * Where is the Wiki how-to page for footnotes? Because I agree with you that footnotes are cleaner and can make the section more succinct. (n/m, found that on your talk page : ) Gaviidae 09:14, 7 July 2006 (UTC)
 * I don't know of any particular source that has basic guidelines for the average Joe Schmuckenberger, although the 3rd-party reports that I ran across (CNN/BBC-style sites) always had a cautioning physician and sometimes the researchers of the particular study themselves cautioning against people reading about some study results and then chompin down aspirin like candy : )
 * I too think that there is so much out there that there could possibly be a link on the Aspirin page to an NSAIDs and Cancer page. I have also run across patients (mostly elderly who believed everything in Reader's Digest-- oh how I hate that publication!!) who were taking a full adult aspirin daily for their hearts (mind you I was not a physician at the time, only working in radiology doing GI studies and such), and I always had to remind them that they needed to ask their doctors first, and that the general aspirin recommendation for cardiovascular health is only a "child" dose, the 81mg chewies found at the drug store, not 325mg!
 * As for the COX-2 studies done by Merck (and I must be the only one who noticed that while Merck voluntarily removed their (otherwise great) drug, Pfizer continued to sell theirs and even later petitioned the FDA for a liquid or inhaled form of their COX-2 inhibitors?), either on this page or in one of the research papers I read (can't remember which, I'll check) it was mentioned possibly why COX-2 inhibitors increased thromboses etc. Maybe that section should be moved or copied to the NSAIDs/cancer section.  It could be added to the current GI bleed warning in the beginning paragraph, along with the Wiki disclaimer "talk to your doc first" etc.  The funny thing is, I seem to remember that there was some statistical reduction in polyps in the Merck study, but the results didn't count as the study was terminated early. It might also be apropo to add near the end of Cancer section the study you mention re adverse cardiovascular effects of non-aspirin NSAIDs-- that's a new one to me.  Maybe a summary of current medical advice generally accepted now at the bottom?  Gaviidae 07:48, 7 July 2006 (UTC)

Molecular Structure
I'd like to point out that the Lewis structure and the space filling structure on the Aspirin page have slightly different configs. The O and OH is swapped. --Russoc4 20:47, 12 September 2006 (UTC)

That doesn't matter, the carbon to which those groups are attached is non-chiral.83.147.180.185 12:44, 5 August 2007 (UTC)

Menstruating women?
Does ASA really cause increased menstrual bleeding? I can't find a reference for this, and actually it doesn't make much sense. The amount of menstrual bleeding should no be affected by any blood thinners, and (in fact) current menstruation is not even a contraindication for thrombolytic therapy. Maybe take out that line or a proper reference. Ksheka 12:43, 24 October 2006 (UTC)
 * This may actually make an interesting section. If anyone wants to take a shot at it, here are some references:

 Ksheka 12:51, 24 October 2006 (UTC)

-Somebody--- I don't know anything about anything, but if somebody does, they might edit the line "Please note that children cannot tolerate as much aspirin per unit body weight as adults can, even when aspirin is indicated.".--Gtg207u 06:42, 3 January 2007 (UTC)

Fatal cases
I checked the references about the number of fatal cases of aspirin overdoses, and the vast majorit are suicide cases, which I added. This made me doubt the statement in the beginning about the several hunderd fatal overdoses occussing annualy, as this is hard to extrapolate from the 52 american cases, given the fact that suicide rates and preferred methods vary greatly across countries. Furthermore, I don't think intentional fatalities an unintentional ones should be counted together when discussing side effects of a drug. Unless someone adds a reference for the worldwide number of unintentional fatalities, I'm going to remove that sentence. 194.94.96.194 12:47, 2 February 2007 (UTC)
 * Done194.94.96.194 16:58, 16 February 2007 (UTC)

Picric Acid
Shouldn't this article mention picric acid, or be linked to the picric acid article, since pure ASA is crucial in the production of picric acid, and is quite often extracted by hobbyists or teachers for demonstrations? 65.103.218.97 23:03, 27 February 2007 (UTC)

Pronunciation
A pronunciation of acetylsalicylic acid would be nice. --Bookinvestor 04:54, 14 March 2007 (UTC)
 * I'm not very IPA-fluent—could someone check the following? Fvasconcellos 22:52, 15 March 2007 (UTC)
 * that is an acurate IPA transciption —The preceding unsigned comment was added by The Right Honourable (talk • contribs) 02:21, 17 March 2007 (UTC).

I have put the above IPA on the main page. Philiprogers 16:53, 8 April 2007 (UTC)

toxicity is not the right term
the section 'toxicity of low dose aspirin' should be called something like 'danger of low dose aspirin'The Right Honourable 02:32, 31 March 2007 (UTC)

introductory section
the paragraph about uses of low-dose aspirin should probably be moved to a new subsection or incorporated into some existing subsection dealing with uses. Right now the introductory section jumps into a discussion of very specialized discussion of use, which is really only one aspect of this rather broad article.

Question COX
Since platelets have no DNA, they are unable to synthesize new COX once aspirin has irreversibly inhibited the enzyme, an important difference with reversible inhibitors.

If Ibuprofen is a reversable inhibitor, how is that? if it affects both COX1 & 2, does it not affect COX1 the same way as aspirin? Even the answers further up don't quite get me. Gaviidae 12:53, 24 April 2007 (UTC)

Of course it does - but after a period of time, ibuprofen etc will dissociate from the COX, which will then start to work again. But aspirin stays permanently bound to the COX enzyme. In normal cells, the cell will just make more, working, COX, but a platelet cannot do this, so its COX is permanently inactivated. Dlh-stablelights 16:37, 15 June 2007 (UTC)

Oral asprin is near SPF 2 publication suggests this reduces UVA photoaging
oral aspirin is effective against UVA generated erythrema http://phot.allenpress.com/photonline/?request=get-document&doi=10.1562%2F0031-8655(2001)074%3C0587:UERCOM%3E2.0.CO%3B2 abstract at

It appears that oral aspirin it is about spf 2 at 250 mg 3 hours prior to UV thus there is the possibility then that time release asprin could halve the rate of photoaging

If you like put this on the main page

Aspirin is very clever
You can take it for rheumatic pain, sciatica, lumbago, headaches, period pain, dental pain and many other things. But how does it know which bit hurts and where it should go? :) -- SteveCrook 00:38, 4 June 2007 (UTC)

Readability
What is a 'centrally mediated vision disturbance'? Njál 22:31, 10 July 2007 (UTC)

Rasputin saves prince Alexei from Aspirin
I removed the paragraph about aspirin possibly given to Russian prince Alexei, who was saved from it by Rasputin. Nothing is known about Alexei taking aspirin. This is just another ridiculous story invented by Diarmuid Jeffreys in his poorly researched book "Aspirin: the remarkable story". In that book Jeffreys also perpetuates the myth that Eichengrun discovered aspirin. It is impossible to trust anything written in the book, which says that in 1856 Gerhardt examined the salicylic acid molecule under the microscope and saw the atoms; the hydroxyl group was rubbing off the stomach wall. If you do not believe me, it is on p47: "One of the many substances Gerhardt examined under his microscope was salicylic acid.[...] The first thing he noticed was that the acid's molecular structure was made of a central structure: a six-carbon benzene ring - with two attached components. These were a hydroxyl group of atoms and a carboxyl group of atoms. The hydroxyl set separated from the core when it rubbed against the stomach wall and it was this that caused the dreadful gastric irritation." Paul gene 00:43, 20 July 2007 (UTC)

 * My paperback copy of this book says "One of the many substances Gerhardt examined closely was salicylic acid.". I wonder if Paul is reading an early hardback edition that hadn't been reviewed thoroughly? Colin°Talk 11:34, 6 September 2007 (UTC)

 * I quoted a 2004 hardcover edition. Even if it does not have the rubbing hydroxyl groups thing, it is still complete nonsense. For example, Gerhard did not examine the acetylsalicilic acid closely, it was just one of about 20 examples in his paper, and he did not even bother purifying it. He did not "aim to replace the hydrogen atom of the hydroxyl group with an acetyl group" - at that time the notion of hydroxyl group did not exist, because the structural theory did not exist. "But it was a tricky process", says Jeffreys. No it was not, all he did was just to mix two compounds", etc, etc Paul gene 00:34, 8 September 2007 (UTC)

 * My goodness, that must have been a rather impressive microscope. I reverted your removal of unsourced claims, however, as I think you inadvertently deleted more than you intended to in a few instances. Zetawoof(ζ) 07:58, 20 July 2007 (UTC)

No it was not inadvertent. Rasputin had a source, so I commented regarding the dubiousness of that source. Separately from Rasputin I also deleted two statements, on which I had put facts tag in May. Since nobody since May sourced those statements, and I have no idea where they are coming from, I deleted them.Paul gene 01:15, 21 July 2007 (UTC)

Aspirin: the remarkable story
I'd like to counter a couple of accusations by Paul Gene about this book. Firstly, let me state that I am aware this is a book written by a journalist for a lay audience. As such it may contain over-simplifications, misunderstandings and mistakes (though the latter are common-enough in expert textbooks, especially early editions). The book has 277 pages of body-text, 32 small-type pages of "Notes and sources", 9 small-type pages of Bibliography and a 13 page index. It received a glowing review by the BMJ, awarded 4 stars out of 4. As a popular science book, it is a good read yet also contains sources for the text. However, I can appreciate that, as an expert, Paul was dissapointed when reading it.

 * The aspirin/Alexei/Rasputin account "is just another ridiculous story invented by Diarmuid Jeffreys in his poorly researched book". This is unfair. The Raputin story is contained within a footnote on page 121. Jeffreys states "It's very likely that to ease the pain the imperial doctors prescribed what, even then, was the world's most popular analgesic". I admit he does then get a bit carried away with the consequences and his book is criticised by some for these tangential stories. However, he does not claim Alexei definitely took aspirin. This story was not "invented" by Jeffreys. His source is.

 * "Jeffreys also perpetuates the myth that Eichengrun discovered aspirin." I'd like to know how Paul has the confidence to call this a "myth". To do so implies that the argument has been settled and ridicules those who maintain an alternative theory. Jeffreys is aware of Sneader's paper (it is in his Bibliography) and appears to side with him. Jeffreys acknowledges that "The exact role Hoffman, Eichengrun and Dreser played in developing aspirin has been the matter of much debate" and also "Although there is considerable controversy over this issue, in my opinion the most reliable...". Jeffreys should be commended for informing his reader of the controversy and that certain aspects of history he relates are "in his opinion". Most journalists are taught to "assume authority" and simply tell the story how they see it.

 * You can read Sneader's paper here and the responses here. Sneader has written several papers on drug discovery and at least one book on the subject. As such, his views should not be lightly dismissed. Sneader responds to each of the letters and doesn't back down. Are there further articles that settle once-and-for-all that Sneader is wrong? If not, the current text is not NPOV. Paul's view may well be correct, but is only one POV. The current text of this article gives the impression that Sneader's paper has been dismissed and calls Eichengrün a "pretender to the title". Such language should not appear on WP except perhaps in a quotation.

I've already noted that the "microscope" gaff seems to have been corrected in later editions. I do wonder how one can honestly say "it is impossible to trust anything written in the book". That seems too harsh when some of the criticisms are just differences of opinion. History is not science; there are some "facts" we will never know for certain. Colin°Talk 13:45, 6 September 2007 (UTC)

 * Colin, you are right about some NPOV. Aspirin was one of the first articles I edited. I removed it, and I answer everything else later. Paul gene 11:41, 7 September 2007 (UTC)

 * It (the Jeffrey'sbook) received a glowing review by the BMJ. Interestingly, it is the first 2004 edition (the one that had the microscope gaffe) that received the glowing review in BMJ. Remember, the book reviews in BMJ are not peer-reviewed, so the BMJ respectability does not extend to them. I guess, some hack wrote it.
 * The "hack" was Boleslav L Lichterman, Centre for the History of Medicine, Russian Academy of Medical Sciences, Moscow, Russia. Some of his work is listed in Pubmed/Pubmed Central. Colin°Talk 15:19, 8 September 2007 (UTC)
 * A hack he is. From the Pubmed you can find out that his day job in an outfit called "Centre for the History of Medicine of Russian Academy of Medical Sciences" is expounding on topics like Medical ethics in Russia before the October revolution and after Russian revolution, and about Basic problems of medical ethics in Russia in a historical context, and about Conflict or harmony of Clinical research and the medical press in Russia. I would not be surprised if he did not read the book in full or even at all. More than 300 pages of English text must have been a lot for him. Paul gene 21:17, 8 September 2007 (UTC)

 * OK, let's presume that it was not Jeffreys but Friend DG who came up with the "Rasputin saves Alexei from aspirin" story. But look at what Jeffreys writes, "It's very likely [my emphasis] that" Alexei's doctors prescribed aspirin. And why is it likely? - because it "was the world's most popular analgesic". So, these are just speculations, and as such unverifiable and have no place in WP. The Nicholas II family doctor was killed together with the emperor's family in 1918, so it is unlikely that the story could come from him. If you can find the Friend DG paper, and see that he cites a memoir from somebody close to the Russian emperor, than I am all for including that fact into the Aspirin article. Paul gene 01:23, 8 September 2007 (UTC)
 * I agree, it is pure speculation and don't think there is any basis for it other than a hunch. Speculation (if attributed) can appear on WP, but WP:UNDUE suggests we shouldn't be reporting what is just a footnote after all... unless other authors have seized on this and it is now a commonly told story. Lets drop this one. Colin°Talk 15:19, 8 September 2007 (UTC)

 * "Jeffreys also perpetuates the myth that Eichengrun discovered aspirin." Before I started reading about aspirin, I had thought too that Sneader did a great thing when he uncovered the fascist conspiracy to promote "arian" Hoffman and forget the real father of aspirin "Jew" Eichengrun. However, as I looked through the available literature, I found that the prevailing point of view among historians and chemists is that neither Hoffman nor Eichengrun discovered aspirin. First of all, everybody, including Jeffreys agrees that Gerhardt was the first to synthesize aspirin. The next question is, who was the first to prepare pure aspirin. It was von Gilm, and he published a paper on the subject in the premier chemical journal of that time. Who established the structure of aspirin - Kraut and coworkers, and they published in the same journal. Now, if you ask who was the author of the aspirin's marketing campaign - the answer would be Eichengrun or Hoffman or Dreiser - but I cannot care less about that answer. I only covered the Eichengrun-Hoffman controversy because so much attention has been paid to it, so it had to be covered. Paul gene 01:46, 8 September 2007 (UTC)

 * It is more than just marketing. Did Hoffman not establish a new process for creating aspirin? If so, he deserves some credit. Some questions: Was that new technique necessary for producing large quantities in a pure form? Is that process still used today? I suspect, that even without the Bayer team, aspirin would have appeared around that time. In other words, it wasn't such a leap of genius. What do you think? Colin°Talk 15:19, 8 September 2007 (UTC)

 * Did Hoffman not establish a new process for creating aspirin? Was or wasn't it such a leap of genius.? The article says it all: "In 1897, Felix Hoffmann, a chemist at Friedrich Bayer & Co., obtained acetylsalicylic acid[7] by a reaction of salicylic acid and acetic anhydride;[8] that is, essentially repeating the Gilm/Kraut procedure but substituting acetic anhydride for acetyl chloride." So, he gets the credit he deserves. There is a discussion later in the article, as to whether his process was novel, and courts in GB and Germany said - no, and in the US - yes. No POV. Answering the questions, Was that new technique necessary for producing large quantities in a pure form? Is that process still used today?, would take a chemist and some original research.  As for the marketing, product development and introduction of aspirin, the consensus appears to be to divide the credit among the three men - Eichengrün, Hoffmann and Dreser, because of the controversy and lack of established facts. My own opinion is that Eichengrün was probably the moving force behind aspirin, and Dreser also played an important role, but mostly because of his position. But this is my personal POV. Paul gene 21:39, 8 September 2007 (UTC)

 * You can read Sneader's paper here and the responses here. "Sneader has written several papers on drug discovery" and so did I, so my views should not be dismissed lightly ;). But lets consider the facts.

 * What is wrong with Sneader's paper? First of all, he discusses "discovery of aspirin", while it would be more correct to speak about "marketing of aspirin". He does not even mention Gerhard, whose role in the discovery of aspirin is recognized by everyone. He also conveniently forgets to mention that the US patent on aspirin has Hoffman's name as the inventor (and this is important since the US law unlike the law in many other countries requires that the real inventor be named, not just any representative of the company.) His article is all based on speculations around the time line of aspirin development, while he dismisses the only solid evidence - the note in Hoffman's notebook. He did not credit the previous research on the history of aspirin (at least three papers), which is a big no-no in science. Paul gene 02:24, 8 September 2007 (UTC)

Aspirin resistance
Aspirin is meant to reduce platelet activation to be of benefit in secondary prevention of strokes and heart attacks. If platelets remain activated (in laboratory assays), the result is termed "aspirin resistance". Until recently it was controversial whether this translates to poorer outcomes in patients. This meta-analysis indicates that people whose platelets remain activated are worse off.

Enter the routine ordering of aspirin resistance tests on everyone who has CVAs or MIs despite aspirin treatment. Hmm. JFW | T@lk  21:38, 13 August 2007 (UTC)

WP:RxCOTW
This article has been selected as the first Pharmacology Collaboration of the Week. The goal during this week is to raise this article to meet the featured article criteria, and nominate it on September 10, 2007 at WP:FAC.

Also, please visit WP:RxCOTW for other nominees for the next collaboration of the week. Dr. Cash 00:15, 5 September 2007 (UTC)

 * My first thoughts on quickly skimming this article are (1) it is massively under-referenced and (2) very listy. Any ideas on how to tackle the first? High-quality, reliable source suggestions welcome! :) Fvasconcellos (t·c) 01:17, 5 September 2007 (UTC)

Is it possible to get a better photo of aspirin crystals/powder? The one already there is way too...white.Jeff Dahl 02:11, 5 September 2007 (UTC)

 * Ugly! And what is so remarkable about aspirin crystals? You could make a shot of salt crystals and call them aspirin, and nobody would notice the difference. Let's remove the photo.Paul gene 09:38, 6 September 2007 (UTC)

 * I agree that the image is very hard to see. Furthermore, it's not really necessary for the article, although to me, salt & aspirin would be quite easy to tell the difference by looking at it (not sure about people without a scientific/chemistry background, though). If a better image could be taken, it **might** go better in the synthesis section, but it's not necessary, so I'll remove it for now. Dr. Cash 18:33, 7 September 2007 (UTC)

Origin of the name
Isn't aspirin a contraction of Acetylirte Spirsäure (acetylated spiræic acid), created by Bayer's Heinrich Dreser? What's this about it being derived from Raffaele Piria's surname? We must find a reference for this, or remove it. Fvasconcellos (t·c) 18:37, 5 September 2007 (UTC)

 * According to Bayer (and they should know that for sure) aspirin comes from acetylated spirsaure. All other versions of the word aspirin origins are nonsense and should be removed, whether there are references or not.Paul gene 09:34, 6 September 2007 (UTC)

 * From the book "Aspirin: The Remarkable Story of a Wonder Drug" by Diarmuid Jeffreys, 2004. ISBN 0-7475-7083-3, page 73:

 * On 23 January 1899, a memo circulated through Bayer's senior management addressing the thorny issue of what the new product should be called. Round robins of this sort were common and allowed everyone to have their say on a range of proposals. Because salicylic acid (as Karl Lowig had found out many years earlier) could be obtained from the meadowsweet plant, the document contained the suggestion that an abbreviation of the plant's Latin genus, Spiraea, should be put at the heart of the new brand name. The letter 'a' could be added at the front to acknowledge acetylation, and the letters 'in' could be tacked on to the end to make it easier to say — as was customary with many medicines of that time. It was noted that there was a drawback to this proposal because it might be suggestive of the word 'aspiration', which wouldn't have been an appropriate metaphor. An alternative could be the name 'euspirin'. When it came to him, Arthur Eichengrün, whose idea the final name probably was, wrote: 'I am in favour of Aspirin because "Eu" is generally used for improved taste and odour.' Carl Cuisberg, Felix Hoffman and Heinrich Dreser all signed without comment.[source: Bayer Leverkusen archives]

 * The book is a great read, BTW. Colin°Talk 11:24, 6 September 2007 (UTC)
 * I've removed the Piria line and reworded the remainder of the statement a bit. Thanks so much for the preceding paragraph, Colin; I've no doubt the book is a great read (I'm personally a Berton Roueché fan), although concerns have indeed been raised about its accuracy ( and I'm not talking about Paul :) (OK, hadn't seen your notes above) Fvasconcellos (t·c) 13:51, 6 September 2007 (UTC)

History: a review
Here is a review of the History section. I've checked the facts against Jeffreys' book. I know Paul thinks this book is worthless, but it is what I've got to hand. As Fvasconcellos notes, this article is undercited. I don't mind whether this book is used as a source within this section or a better source found. It meets WP:RS, though I wouldn't dare to use it for medical or chemistry facts (see discussions on talk WP:MEDRS for where I've argued against the use of journalist's text for medical facts).

 * The Hippocrates sentence is confirmed on p15, but with a qualification: "Hyppocrates recommended the bark of the willow tree as an analgesic, although in this case it was as a remedy for the pains of childbirth and as a fever reducer." Perhaps our text should say "ease the pains of childbirth and reduce fever"?

 * On p11, a Sumerian tablet is mentioned, which lists willow along with numerous other remedies. Unfortunately, the tablet does not indicate what the remedy is for.

 * On p12, the Ebers Papyrus is noted to have three references to willow as "a general purpose tonic or as some kind of pain reliever and anti-inflammatory therapy". Jeffreys casts some doubt as to whether the remedies would have actually worked.

 * Lebanon, Assyria and the Cherokee aren't mentioned so I can't confirm the text here. On p28 he notes willow appears in sixth century Chinese medical texts (unclear indications) and some evidence of use by indigenous tribes in southern Africa and by Amerindians (neither had a written medical tradition, though).

 * Jeffreys devotes a whole chapter to Reverend Stone. The sentence in our text could be expanded into its own paragraph:

 * The Reverend Edward Stone, a vicar from Chipping Norton, Oxfordshire, England, discovered in 1758 that the bark of the willow was effective in reducing a fever. Stone claims to have accidentally tasted willow bark and noted its bitterness was similar to the bark from cinchona, whose extract quinine was known to be effective in treating fever and agues (due to malaria). Stone was familiar with the doctrine of signatures, which held that the source of an illness (boggy grounds) and its cure (willow trees nearby) were often found together. Over then next five years, Stone experimented on 50 subjects and claimed near universal success. In 1763, he wrote of his discovery in a letter to George Parker, 2nd Earl of Macclesfield and president of the Royal Society, which was subsequently published in the society's Philosophical Transactions.

 * Jeffreys book disagrees somewhat with the current text wrt to isolation of salicin. He claims (p38-9) the first person was Joseph Buchner, Professor of Pharmacy at Munich University. He obtained a tiny amount of "bitter-tasting yellow crystals" in 1828 and "christened it salicin (after salix, the Latin anme for willow)". Leroux is credited with refining the extraction procedure in 1829, and "obtained around 25 g of salicin crystals from one kilo of willow bark". In 1838, Raffaele Pira produced a more potent acid from the crystals, which he called "salicylic acid".

 * According to Jeffreys, the extraction from meadowsweet occurred in two stages: Swiss pharmacist Johann Pagenstecher extracted what he believed was the "therapeutic essence" and used it to treat pain. His report in a Swiss journal was discovered by the German Karl Jacob Lowig who obtained some of this tincture and transformed it into an acid, which he called "spirsaure" and tested its effects on reducing fever and pain. He had independently discovered salicylic acid.

 * Over pages 49-55, Jeffreys tells the story of Thomas John MacLagan and his experiments with salicin. He credits Maclagan with performing the first scientific study (of such compounds) and using a simple control process in his trial. The results were published: Maclagan, T. J., 'The treatment of acute rheumatism by salicin', Lancet, 4 March 1876. There followed a "flurry" of other papers documenting the success of salicylic acid. On his death in 1903, The Lancet proclaimed "Dr Maclagan would seem to have been the first to draw the attention of the medical profession to the use of salicin in modern days." I believe Maclagan deserves a mention at the end of this section.

 * Gerhardt's creation of ASA is covered in pages 46-7. Jeffreys' explanation of the chemistry might be shakey, but there are a couple of points worth adding. "he only managed to obtain a crude and impure version of the final substeance" and "Gerhardt found the whole procedure so lengthy and tedious that he decided to shelve it". Jeffreys also notes that Gerhardt's home town of Strasbourg has a memorial that recognises his place in the history of Aspirin.

 * The Gerhardt and von Gilm paragraphs contain footnotes that cite the original papers. As primary texts, they are unable to substantiate much of the discussion within these paragraphs. In addition, these papers are not available online or in English. As such, I suspect that WP editors haven't read them. I therefore strongly recommend the citations are ammeded with "as cited by ...." and a secondary source listed that is the true source of the information.

 * Jeffreys' book doesn't mention von Gilm nor Schröder, Prinzhorn and Kraut. A secondary source is required for this information. It would be nice if we could discover what von Gilm's forename was (begins with H).

That's as far as I've reviewed so far. Colin°Talk 18:43, 6 September 2007 (UTC)
 * Looks good. (Concise, I know :) I honestly have no reason to think the book's historical research would be objectionable, particularly since the facts surrounding aspirin's early history appear so...muddy. It has been mentioned, AFAIK, that Eichengrün's claims were dismissed because he was Jewish; apparently Jeffreys' book covers this? It would certainly warrant a mention here. Fvasconcellos (t·c) 22:48, 6 September 2007 (UTC)
 * By the way, Colin, I presume the Reverend Stone paragraph above is not a direct quote from the book; I think it should be added to the article. Fvasconcellos (t·c) 19:14, 7 September 2007 (UTC)
 * The paragraph is my wording, based on the whole chapter. I've left Paul a message on his talk page. Unless someone's got a better source, or Paul feels the book really is a worthless source, then I'll incorporate what I can into the article. That still leaves some unsourced text. I'll try to look at the rest of the history over the weekend. Colin°Talk 21:30, 7 September 2007 (UTC)

 * The Hippocrates sentence is confirmed on p15 "Hippocrate, le père de la médecine moderne, recommandait une tisane de feuilles de saule pour soulager les douleurs de l'enfantement et du jus d'écorce de peuplier pour certaines atteintes oculaires." see H. Lévesque1 and O. Lafont, L'aspirine à travers les siècles: Rappel historique, La Revue de Médecine Interne,Volume 21, Supplement 1, March 2000, Pages S8-S17 Paul gene 14:20, 8 September 2007 (UTC)
 * Hmmm. The above text describes a "herb tea of willow leaves to relieve the pains of the childbirth". The English abstract at says "chewing willow leaves for analgesia in childbirth". Was it tea or chewing that he recommended? Lots of sources for either on Google/PubMed. Several sources mention bark, bitter powders and reducing fever. I wonder if Hippocrates described two different treatments, using different parts of the tree, for fever and for pain in childbirth. What I've yet to find is a source that actually cites the Hippocratic corpus. Perhaps Lévesque/Lafont do, but their abstract disagrees with their text. I'd like to get this right as otherwise Wikipedia is just repeating all the cumulative mistakes of past writers. Colin°Talk 20:32, 12 September 2007 (UTC)
 * There is no inconsistency between the text of the Levesque article and its abstract in French: "Initialement utilisée sous forme de décoctions à base de feuilles ou d'écorce de saule par les Égyptiens et les Sumériens puis par Hippocrate, pour prévenir les douleurs de l'enfantement, et plus tard par le révérend Edward Stone (premier auteur à montrer scientifiquement son efficacité) pour traiter les fièvres, il fallut attendre le XIXe siècle pour découvrir le principe actif, et les caractéristiques de la salicine." However, in this quotation, Levescue refers to Mueller RL, Scheidt S. History of drugs for thrombotic disease. Discovery, development, and directions for the future. Circulation. 1994 Jan;89(1):432-49. This article is available free from the journal's website http://circ.ahajournals.org/cgi/reprint/89/1/432 and gives a very nice overview of the aspirin's history (better than Levescue's IMHO). It says: "The first recorded descriptions of therapeutic benefits of extracts of willow bark and other plant sources of salicylates were made by Hippocrates, the father of modern medicine, 2400 years ago.4 He recommended chewing willow leaves for analgesia in childbirth and the juice of the poplar tree for eye diseases." and refers to 4. Gross M, Greenberg LA. The Salicylates: A Critical Bibliographic Review. New Haven, Conn: Hillhouse Press; 1948:1-8. This appeared to be more reliable reference. However, in the 1856 edition of the Hippocrates' full works (available free at http://web2.bium.univ-paris5.fr/livanc/?intro=hipp_vf&statut=charge) there is only a single mention of willow (v 8, p 187): "Fumigation expulsive, capable aussi de faire sortir du sang hors de la matrice: mettre des feuilles de saule sur le feu et fumiger; on fera asseoir la femme et on la laissera jusqu’a ce que la vapeur entre dans matrice." Poplar bark (which also contains salicilin and other salycilates) is mentioned several times. More on this later. Paul gene 04:14, 13 September 2007 (UTC)
 * Oh the whole thing has got terribly confused. Mueller/Scheidt's language isn't very precise at times. Sentences that mention "willow bark" at the beginning and "willow leaves" at the end don't help clarify things. It also doesn't help that they say it is "the first recorded description" when Levescue and others mention Egyptians and Assyrians as being earlier (though I get the impression that it is difficult to always know precisely what they thought the medicine was good for). Finally, they credit Galen with the first antipyretic usage, not Hippocrates. My current gut feeling is that "chewing willow leaves for analgesia in childbirth" is correct and that willow bark has been wrongly associated with Hippocrates (at least as far as pain relief is concerned) due to either imprecise language or confusing things with Stone's usage of bark. Also, there are doubts about Hippocrates using willow for fever reduction.
 * Before mentioning poplar bark for eye diseases, do we know that the therapeutic effect (whatever that may be) was due to the salycilates? Colin°Talk 12:43, 13 September 2007 (UTC)

 * On p12, the Ebers Papyrus is noted to have three references to willow "Les Égyptiens connaissaient les propriétés antalgiques de la myrte et des feuilles de saule. Dans le papyrus Ebers [4], il existe une description très précise d'états inflammatoires répondant bien à la prise de tisanes à base de feuilles de saule (figure 1)." see Lévescue (2000) Paul gene 14:26, 8 September 2007 (UTC)

 * Gerhardt's creation of ASA is covered in pages 46-7. Jeffreys' explanation of the chemistry might be shakey, but there are a couple of points worth adding. "he only managed to obtain a crude and impure version of the final substeance" and "Gerhardt found the whole procedure so lengthy and tedious that he decided to shelve it". Sorry, but the last sentence is another example of Jeffreys' inventions. The procedure was very easy, and you can read it in the text of the Aspirin article. I also doubt very much that Jeffreys has any sources regarding Gerhardt "deciding to shelve it". By the way, according to the patent law and chemistry custom, it is often enough to prepare substantially pure (not pharmaceutically or analytically pure) compound to claim a priority for compound, and Gerhard, probably satisfies this requirement. Paul gene 02:47, 8 September 2007 (UTC)
 * One of your sources below confirms that Gerhardt's product wasn't pure, which I think we should mention. If it isn't pure enough to use as a safe medicine, then the improvements made by later chemists are significant. Colin°Talk 15:49, 8 September 2007 (UTC)
 * Agree, I just presumed that the fact that Gerhardt made only crude compound would be clear from the description. Paul gene 22:37, 8 September 2007 (UTC)

 * The Gerhardt and von Gilm paragraphs contain footnotes that cite the original papers. As primary texts, they are unable to substantiate much of the discussion within these paragraphs.
 * I disagree. See WP:PSTS: "Primary sources that have been published by a reliable source may be used in Wikipedia, but only with care, because it is easy to misuse them. For that reason, anyone—without specialist knowledge—who reads the primary source should be able to verify that the Wikipedia passage agrees with the primary source." "An article or section of an article that relies on a primary source should (1) only make descriptive claims, the accuracy of which is easily verifiable by any reasonable, educated person without specialist knowledge, and (2) make no analytic, synthetic, interpretive, explanatory, or evaluative claims". Which is exactly what I did, the corresponding paragraphs contain only short description of the relevant experiments and no comments or evaluation.
 * OK, on reviewing what I wrote I think the "much" isn't justified. However, the claim that "Gerhardt, was first to prepare acetylsalicylic acid" can't be taken from his paper (even if he himself boasts of it, he isn't unbiased and history (as often happens) might have shown him to be ignorant of some discovery elsewhere). Similarly "he did not pursue it further." probably can't come from the paper. In the second paragraph, "They were first to assign to it the correct structure" must come from a secondary source. Colin°Talk 15:49, 8 September 2007 (UTC)

 * In addition, these papers are not available online or in English. As such, I suspect that WP editors haven't read them.
 * Wrong, they are available online: see http://www3.interscience.wiley.com/cgi-bin/jissue/112322225 and http://www3.interscience.wiley.com/cgi-bin/jissue/112322853. Or you can order them free through an interlibrary loan. And knowledge of basic German is not a specialist knowledge, is it? And I did read them. Moreover, the articles are very old so they are not copyrighted. I could post images or PDFs somewhere but they are large. I can e-mail them too. The chemistry described in the papers does not go beyond the high school chemistry, and what is described in the Preparation chapter of the Aspirin article. Paul gene 03:18, 8 September 2007 (UTC)
 * Paul, I apologise for significantly underestimating you (though I didn't actually check/know who wrote those bits of the history section). WP is indeed fortunate to have such an expert. I can't read German. I think we should link to the online versions by using the DOI. Colin°Talk 15:49, 8 September 2007 (UTC)

 * secondary source listed... Here you go.

 * "The French chemist Charles Gerhardt was the first to synthesise acetylsalycilic acid in a crude form in 1853. In spite of the achievement of Gerhardt, the invention was ignored until 1859 when it was prepared again by von Gilm. Ten years later the German Karl Kraut found an improved synthetic method of making acetylsalicylic acid but, again, it was ignored…Arthur Eichengrun, who was responsible for pharmaceutical development, had an idea to develop much-needed version of salicylic acid with a better toxicity profile. This development was put in the hands of a 29-year-old chemist, Felix Hoffmann… In 1893 when Hoffmann searched the literature on salicylate derivatives he found the works of Gerhardt and Kraut. Hoffman developed an improved synthetic pathway to acetylsalycilic acid between 1893 and 1897, which he described in his laboratory notebook on 10 October 1897." T Hedner, The early clinical history of salicylates in rheumatology and pain, Clinical Rheumatology, v 17, no1, 1998, p17-25. Paul gene 03:43, 8 September 2007 (UTC)

 * "Like many legends, the aspirin story is not completely untrue. Hoffmann truly did synthesize acetylsalicylic acid. He may even given some to his father. Alas, Hoffmann found ASA not so much in the laboratory as in the library: It had been created in a crude form back in 1853 by a French chemis, Charles Frederic Gerhardt, and synthesized in a purer form sixteen years later by Karl Johann Kraut, a German. (Hoffmann's methos of making ASA, however, was an improvement over that of his predecessors.)" Charles C. Mann and Mark L. Plummer (1991). The aspirin wars: money, medicine, and 100 years of rampant competition. Boston, Mass: Harvard Business School Press, p. 25 Paul gene 03:55, 8 September 2007 (UTC)
 * Do you think we should remove the "gave to his father" legend (even Bayer use the word "legend")? Eichengrun seems to deserve the credit for starting the "lets improve on salicylic acid" task at Bayer. Colin°Talk 15:49, 8 September 2007 (UTC)
 * No we should not remove the legend; it is is an important part of the mass culture. Paul gene 22:37, 8 September 2007 (UTC) In my personal opinion Eichengrün would deserve the credit but there is no proof, except for his own claims and Sneader's time line speculations. Paul gene 23:52, 8 September 2007 (UTC)
 * Here is waht the best source (IMO) Mann (1991), p 25-36 tells us:

 * " Bayer's drug lab was split into two parts: a pharmaceutical section, which developed new drugs and was run by Arthur Eichengrün, a researcher with several successful products already under his belt; and a pharmacological section, which tested the drugs and was directed by Heinrich Dreser, a respected professor from the University of Bonn. The idea of a separate testing facility was Duisberg's. Fearful of incurring doctors' wrath by shipping drugs that didn't work, Duisberg wanted an additional check that would weed out all but the best remedies. Any drug developed by Eichengrün's lab would be passed on to Dreser's lab for his approval. As one of the new lab's first projects, Eichengrün chose to search for a version of salicylic acid with fewer side effects. ...
 * The lack of novelty did not discourage Eichengrün, who passed ASA to Dreser for testing. It was not a hit. Many doctors believed that salicylic acid had an "enfeebling action on the heart"; declaring that acetylsalicylic acid would necessarily share that enfeebling action, Dreser rejected ASA out of hand.* (Mann's footnote:* The reason for this erroneous belief is hard to ascertain, although it may have come from the then-common use of salicylic acid in massive doses to ease the pain and swelling of rheumatic fever. Given what in modern terms would be regarded as an overdose of salicylic acid, patients pant for breath and feel their hearts race. From this, doctors apparently concluded that salicylates can exhaust the heart.) For more than a year, what was destined to be the most successful drug ever invented sat on a shelf....
 * Acetylsalicylic acid remained among the drugs rejected by the pharmacological laboratory, until it was again brought to Dreser's attention late in 1898. How this occurred is a matter of dispute. Decades afterward, Eichengrün asserted rather angrily that it was only through his efforts that ASA was reconsidered by Dreser, and that he, Eichengrün, had believed from the start that ASA was the most promising medication yet developed by the lab. Dreser's contract gave him a veto over all clinical testing. His opposition to ASA, the irate Eichengrün wrote, had been a "death sentence" for the drug.
 * Vexed by Dreser's rejection, Eichengrün tested the new drug on himself. When his heart was not poisoned, he decided to examine it further. While ASA sat in Dreser's lab, Eichengrün surreptitiously passed it to doctors in Berlin, who administered it to their patients. ASA not only eased the discomfort of fevers and aching joints, they learned, it also soothed headaches. Significantly, it had many fewer side effects than salicylic acid or any of the variants of salicylic acid on pharmacy shelves.
 * One of the doctors, Felix Goldmann, was Bayer's representative in Berlin, the nation's capital, cultural center, and biggest city. He delivered an enthusiastic report on ASA to the company's management. Asked his opinion of Goldmann's memo, Dreser growled: "This is the usual Berlin bragging; the product has no value." At this point, according to Eichengrün, Duisberg himself came to the rescue. He insisted that tests be conducted by an outside pharmacologist. The results were glowing. Finally acceding, Dreser wrote a scientific paper extolling ASA. In it he neglected to mention Hoffmann and Eichengrün." Paul gene 17:34, 9 September 2007 (UTC)

 * "Même si son nom est toujours resté dans l'ombre le premier à avoir synthétisé l'aspirine est un chimiste français de renom [5], le pharmacien Charles-Frédéric Gerhardt (1816-1856), qui fut un temps professeur à l'École supérieure de pharmacie de Strasbourg, dont le rôle, dans le développement de la théorie atomique fut considérable et qui introduisit la notion de série homologue en chimie [28]. Présentés en mai et juin 1852, puis publiés l'année suivante en français [29] et en allemand [30], ses travaux portant sur les anhydrides d'acide, consistaient à faire réagir le sel de sodium d'un premier acide carboxylique avec le chlorure d'acyle provenant de l'halogénation d'un second acide organique. Il eut l'idée de faire réagir le salicylate de sodium sur le chlorure d'acétyle. Il considéra que la substance blanche qu'il avait isolée était l'anhydre mixte de l'acide salicylique et de l'acide acétique. Il la nomma « acide acéto-salicylique ». En fait, c'est l'acide acétylsalicylique qu'il avait obtenu, sans toutefois l'identifier [31] ! Ce n'est qu'en 1859 que l'acide acétylsalicylique fut consciemment synthétisé par H. von Gilm, par action de l'acide salicylique sur le chlorure d'acétyle [31], et en 1869 que ce produit fut identifié à celui que Gerhardt avait synthétisé seize ans plus tôt [32]. Il ne s'agissait alors que de chimie organique pure, sans visée thérapeutique particulière." H. Lévesque1 and O. Lafont, L'aspirine à travers les siècles: Rappel historique, La Revue de Médecine Interne,Volume 21, Supplement 1, March 2000, Pages S8-S17 (sorry for the typos) Paul gene 04:20, 8 September 2007 (UTC) I just only corrected the typos in the above quotation and did not change anything else, I hope it is OK with you. Paul gene 15:21, 8 September 2007 (UTC) Lévesque (2000) further goes on: "En 1895, décidant de s'intéresser aux produits pharmaceutiques, cette société fait appel au pharmacologue Heinrich Dreser et au docteur Arthur Eichengrün et engage une dizaine de chimistes dont le pharmacien Felix Hoffmann dont l'un des sujets de recherche proposés portait sur l'élaboration d'un dérivé de l'acide acétylsalicylique moins toxique. La légende suggère que le père de ce jeune chimiste souffrant d'un rhumatisme inflammatoire, calmé par l'acide salicylique, mais le tolérant mal sur le plan digestif, aurait demandé à son fils de lui trouver un remède miracle. Ce dernier se plongeant dans les travaux de Gerhardt et de Kraut et adaptant peut-être la technique imaginée par le Russe Marcellus Nencki (1847-1901), redécouvrit l'acide acétylsalicylique (figure I). Felix Hoffmann proposa donc l'utilisation de cette molécule qui fut initialement refusée par Dreser, du fait d'une possible cardiotoxicité sur la grenouille." Paul gene 15:46, 8 September 2007 (UTC)

I have another 2 refs, let me know if you need quations from them. Paul gene 04:26, 8 September 2007 (UTC)

 * Jeffreys' book doesn't mention von Gilm nor Schröder, Prinzhorn and Kraut. A secondary source is required for this information. It would be nice if we could discover what von Gilm's forename was (begins with H). Well, did I not tell you that Jeffreys' book is poorly sourced? Von Gilm's name - only H is in the original, sorry. Paul gene 04:26, 8 September 2007 (UTC)
 * Shame about the H. Including forenames is the sort of reader-friendly thing we should do. It is one good thing about a pop-science source compared to a medical paper :-) Colin°Talk 15:49, 8 September 2007 (UTC)

 * Jeffreys book disagrees somewhat with the current text wrt to isolation of salicin. "However, the earliest attempts to isolate an active principle from willow bark were made by the Italians Fontana and Brugnatelli. Between 1826 and 1829, they managed to isolate small amounts of the glycoside compound salicin [4]. German and French scientists were also trying to isolate an active principle from natural sources and, in 1828, Buchner in Munich also isolated salicin [4]. A year later, the Frenchman Leroux managed to do the same task and also demonstrated its antipyretic activity [5]. Some years later, in 1833, Merck in Darmstadt made the same discovery and isolated salicin from willow bark [5]." see Hedner (1998) Paul gene 12:15, 8 September 2007 (UTC)

"Other early achievements in pharmaceutical chemistry were made by the Swiss pharmacist Pagenstecher who, in 1831, distilled salicylaldehyde from the meadowsweet or the queen of the meadow plant (Spiraea ulmaria, now Filipendula ulmaria) [6]. A further important step was taken by the Swiss chemist Lowing in 1835 [5], who became the first to prepare salicylic acid. In Paris, salicylic acid was isolated by Piria in 1838 from the willow bark glycoside salicin [5] and a year later Dumas showed that Lowing's and Piria's compounds were identical. Both scientists had prepared salicylic acid, one working with salicin from willow bark, and the other working with salicylaldehyde from meadowsweet [5]. In the New World, the American William Procter and the Frenchman Auguste Cahours were working with wintergreen (Gaultheria procumbens and G. hispudula), which was an old folk remedy for 'aguish disorders' [6]. In 1843 they managed to isolate methyl salicylate and in the following years Cahours described how to hydrolyse methyl salicylate to salicylic acid [6]." see Hedner (1998) Paul gene 12:25, 8 September 2007 (UTC)
 * According to Jeffreys, the extraction from meadowsweet occurred in two stages

 * Over pages 49-55, Jeffreys tells the story of Thomas John MacLagan and his experiments with salicin. He credits Maclagan with performing the first scientific study (of such compounds) and using a simple control process in his trial. "Si les caractéristiques et les modalités d'extraction furent plus ou moins rapidement précisées, il était important de vérifier que cette salicine jouissait réellement des propriétés fébrifuges revendiquées soixante ans auparavant par le clergyman anglais Edward Stone. Nous avons vu les réserves émises par plusieurs auteurs tels Trousseau [17] ou Foy [18], cependant un certain nombre d'expériences tentées dans les hôpitaux parisiens furent concluantes et le célèbre médecin Magendie pouvait affirmer qu'à la posologie de 1 g par jour en trois prises elle coupait les fièvres du jour au lendemain et ceci quel que soit leur type. De fait, dans les traités de médecine et de thérapeutique de la tin du XIX siècle, l'efficacité de la salicine ne semble plus discutée : l'accord est unanime aujourd'hui pour reconnaître l'efficacité absolue de la médication salicylée [24], le salicylate de soude employé depuis bientôt vingt ans n'a plus à faire ses preuves [25]. En 1874, un médecin de Dundee, T.J. Mac Lagan, également influencé par la théorie des signatures, fit les mêmes constatations que le révérend Stone et décida de rechercher un remède contre le rhumatisme articulaire aigu parmi les Salicaceae, connues pour contenir de la salicine. Après avoir pris lui-même 5 puis 10 puis 30 grains (envi-mn 2 g) de salicine, sans ressentir le moindre inconvénient, il décida de donner à un patient, « porteur d'un rhumatisme articulaire très avancé », 12 grains de salicine toutes les trois heures. Les résultats dépassèrent tout ce que je pouvais espérer, avec notamment une chute de la fièvre etc une diminution de la douleur et de l'enflure des articulations. Il observa alors des résultats similaires chez huit autres patients rhumatisants (quatre formes aiguës, trois subaiguës et une chronique) [26]. Quelques semaines plus tard, dans une lettre réponse au Lancet, le docteur Ensor, exerçant au cap de Bonne-Espérance en Afrique du Sud, signalait que les Hottentots, peuplade primitive, connaissaient l'effet antirhumatismal du saule depuis de nombreuses années. En effet, dans sa lettre pleine d'humour, il signale l'observation d'une femme souffrant, d'après ses termes, de la plus féroce attaque de rhumatisme articulaire aigu qu'il ait jamais vu, à laquelle il proposa le traitement habituel à cette époque (poudre de Dover et calomel). Revoyant la malade deux mois plus tard, totalement asymptomatique, il se félicita de son traitement jusqu'à ce que cette dernière, lui expliquant que son traitement ayant été un échec total, elle avait consulté un vieux berger hottentot. qui avait préconisé une décoction de feuilles de saule après en avoir pris pendant plusieurs jours, les douleurs commencèrent à diminuer et finalement disparurent complètement [in 5]" see Lévescue (2000) Paul gene 14:57, 8 September 2007 (UTC)

 * Thanks for taking the time to dig out and type up all this. I've not got time to digest all the above at the moment. The question is: are you going to incorporate these sources and extra facts into the text or shall I? Colin°Talk 15:49, 8 September 2007 (UTC)
 * No problem, I used OCR software;), and I have had the PDF files of the references for a long time. Please incorporate the references into the article as you see fit; thank you for your help. Paul gene 23:52, 8 September 2007 (UTC)

"The mechanism of action of aspirin"
Free full text of Vane's short 2003 review. A very interesting read. Fvasconcellos (t·c) 21:17, 9 September 2007 (UTC)

Yes, it is very interesting. I suggest putting a link to this review at an appropriate place in the article. Dirac66 02:08, 16 September 2007 (UTC)

Done. Dirac66 (talk) 17:13, 31 December 2007 (UTC)

Breast cancer risk
This news link claims "A new study has found that aspirin use can cut the risk of breast cancer by almost 25 percent." The study is, and such a lofty claim could use confirmation. Full text, anyone? Fvasconcellos (t·c) 21:54, 9 September 2007 (UTC)
 * Here's an exact quote from the discussion section of the paper and is repeated in the abstract:
 * "We observed no association between aspirin use or total NSAID use and breast cancer risk among the female members of the Multiethnic Cohort study, but we did observe a protective effect of other NSAID use among current users..."
 * So the "protective effects" only show up with non-aspirin NSAIDs. Funny how the news media grabs on to the story they want to see rather than what is actually there. Jeff Dahl 17:47, 13 September 2007 (UTC)
 * Indeed. Thanks for finding this—I could have at least read the abstract :P Fvasconcellos (t·c) 22:38, 13 September 2007 (UTC)

Yet another myth - Hippocrates prescribed willow bark to his patients for pain relief
I copied the discussion on Hippocrates from above for convenience.Paul gene 01:02, 15 September 2007 (UTC)

"Hippocrate, le père de la médecine moderne,     recommandait une tisane de feuilles de saule pour soulager les douleurs de      l'enfantement et du jus d'écorce de peuplier pour certaines atteintes      oculaires." see H. Lévesque1 and O. Lafont, L'aspirine à travers les     siècles: Rappel historique, La Revue de Médecine Interne,Volume 21,      Supplement 1, March 2000, Pages S8-S17 Paul gene 14:20, 8 September 2007 (UTC)
 * The Hippocrates sentence is confirmed on p15, but with     a qualification: "Hyppocrates recommended the bark of the willow tree      as an analgesic, although in this case it was as a remedy for the pains of      childbirth and as a fever reducer." Perhaps our text should say      "ease the pains of childbirth and reduce fever"?
 * Hmmm. The     above text describes a "herb tea of willow leaves to relieve the      pains of the childbirth". The English abstract at  says      "chewing willow leaves for analgesia in childbirth". Was it tea      or chewing that he recommended? Lots of sources for either on      Google/PubMed. Several sources mention bark, bitter powders and reducing      fever. I wonder if Hippocrates described two different treatments, using      different parts of the tree, for fever and for pain in childbirth. What      I've yet to find is a source that actually cites the Hippocratic corpus.      Perhaps Lévesque/Lafont do, but their abstract disagrees with their text.      I'd like to get this right as otherwise Wikipedia is just repeating all      the cumulative mistakes of past writers. Colin°Talk 20:32, 12 September 2007 (UTC)
 * There is no     inconsistency between the text of the Levesque article and its abstract in      French: "Initialement utilisée sous forme de décoctions à base de      feuilles ou d'écorce de saule par les Égyptiens et les Sumériens puis par      Hippocrate, pour prévenir les douleurs de l'enfantement, et plus tard par      le révérend Edward Stone (premier auteur à montrer scientifiquement son      efficacité) pour traiter les fièvres, il fallut attendre le XIXe siècle      pour découvrir le principe actif, et les caractéristiques de la      salicine." However, in this quotation, Levescue refers to Mueller RL,      Scheidt S. History of drugs for thrombotic disease. Discovery,      development, and directions for the future. Circulation. 1994      Jan;89(1):432-49. This article is available free from the journal's      website http://circ.ahajournals.org/cgi/reprint/89/1/432 and gives a very nice overview of the aspirin's      history (better than Levescue's IMHO). It says: "The first recorded      descriptions of therapeutic benefits of extracts of willow bark and other      plant sources of salicylates were made by Hippocrates, the father of      modern medicine, 2400 years ago.4 He recommended chewing willow leaves for      analgesia in childbirth and the juice of the poplar tree for eye      diseases." and refers to 4. Gross M, Greenberg LA. The Salicylates: A      Critical Bibliographic Review. New        Haven, Conn:      Hillhouse Press; 1948:1-8. This appeared to be more reliable reference.      However, in the 1856 edition of the Hippocrates' full works (available      free at http://web2.bium.univ-paris5.fr/livanc/?intro=hipp_vf&statut=charge) there is only a single mention of willow (v 8, p      187): "Fumigation expulsive, capable aussi de faire sortir du sang      hors de la matrice: mettre des feuilles de saule sur le feu et fumiger; on      fera asseoir la femme et on la laissera jusqu’a ce que la vapeur entre      dans matrice." Poplar bark (which also contains salicilin and other      salycilates) is mentioned several times. More on this later. Paul gene 04:14, 13 September 2007 (UTC)
 * Oh the whole     thing has got terribly confused. Mueller/Scheidt's language isn't very      precise at times. Sentences that mention "willow bark" at the      beginning and "willow leaves" at the end don't help clarify      things. It also doesn't help that they say it is "the first recorded      description" when Levescue and others mention Egyptians and Assyrians      as being earlier (though I get the impression that it is difficult to      always know precisely what they thought the medicine was good for).      Finally, they credit Galen with the first antipyretic usage, not      Hippocrates. My current gut feeling is that "chewing willow leaves      for analgesia in childbirth" is correct and that willow bark has been      wrongly associated with Hippocrates (at least as far as pain relief is      concerned) due to either imprecise language or confusing things with      Stone's usage of bark. Also, there are doubts about Hippocrates using      willow for fever reduction.
 * Before     mentioning poplar bark for eye diseases, do we know that the therapeutic      effect (whatever that may be) was due to the salycilates? Colin°Talk 12:43, 13 September 2007 (UTC)

 * First, background. There have been no printed translations to English of the parts of Hippocratic Corpus, namely Diseases of Women and Nature of Women, that mention the use of willow and poplar. The most complete and authoritative translation of the Corpus to a contemporary European language is Oeuvre complètes d'Hippocrate. Ed. Emile Littré. 10 vols. Paris, J.B.Bailliére, 1839-1861, mentioned above and now freely available online at http://web2.bium.univ-paris5.fr/livanc/?intro=hipp_vf&statut=charge. An English translation from Greek of the part I of The Diseases of Women done by Kathleen Whiteley as a part of her MA work at the University of South Africa is freely available online at http://etd.unisa.ac.za/ETD-db/theses/available/etd-06142004-162341/unrestricted/04dissertation.pdf. Whitely tries to make the text more understandable for the contemporary reader but this does not always work.

 * The above passage about willow leaves fumigation (v 8, p187) Whiteley translates as "Fragrant medication for expelling the foetus or placenta, also enabling the woman to expel blood from the belly: put willow leaves on a fire, fumigate, and make the woman sit until the smoke goes into the womb."

 * Poplar
 * v 8, p 183. Littré: "Autre moyen expulsif ... bien neuf cocons rèsineux du peuplier de Crète, piler, boire dans du vin." Whiteley: "Another means of expelling the placenta: ... let her drink nine seeds from the black poplar of Crete ground into wine." Here I do not know how neuf cocons resineux can turn into nine seeds.
 * v 8, p 229 Littré: "Pour l’argémon: larme de peuplier, lait de femme, mêler et s’en servir." Whiteley: "For albugo (A white speck on the eye - LSJ) you must use black poplar sap mixed with breast milk." Paul gene 01:02, 15 September 2007 (UTC)
 * v 7 p349 Littré: "chasse le chorion ...Autre: prenez des noeuds résineux, au nombre de neuf, du peuplier de Crète (populus gracia), pilez-les et faites-les boire dans du vin, c'est un moyen qui favorise aussi la délivrance quand l'accouchement est laborieux." (Use http://babelfish.altavista.com/tr for a quick and dirty translation to English.)
 * v 8 p357 as a part of multicomponent concoction "pour la matrice".

 * The bottom line is, there is no indication in Hippocratic Corpus of any use of willow as a pain medication or for inflammation. The Corpus recommended willow leaves fumigation or poplar parts in vine for expelling fetus, placenta or chorion, or helping with difficult delivery. Poplar sap in breast milk could be used for an eye disease. Paul gene 01:53, 15 September 2007 (UTC)

Move salicylic acid to a separate page?
As has been pointed above, aspirin has a different mechanism of action than salicylic acid, which is related to its acetyl group. Should these two compounds share the same page? Paul gene 02:07, 22 September 2007 (UTC)
 * Erm, they don't? Fvasconcellos (t·c) 02:14, 22 September 2007 (UTC)
 * Here is what this (ASPIRIN) article says: " Aspirin acts as an acetylating agent where an acetyl group is covalently attached to a serine residue in the active site of the COX enzyme." And there is no acetyl group in salicylic acid. Also see: http://en.wikipedia.org/wiki/Talk:Aspirin#Action_of_salicylic_acid.3F It is good that salicylic acid has its own page, so we can move all the ancient history there. Paul gene 14:24, 22 September 2007 (UTC)

Here's some lay comments/questions:
 * Any popular or medical article discussing the history of aspirin includes the history of salicylates. We'd have to have pretty good NOR reasons for excluding them.
 * Aspirin has multiple therapeutic uses, not all of which share the same mechanism of action. The article perhaps doesn't make this clear. For example, the last sentence hints that reducing inflammation is a property of the salicylates. The principle pain-relief mechanism seems to be aspirin-specific (if I interpret this discussion correctly) but if the salicylates have pain relief / fever reduction properties, does aspirin also share those properties? In other words, does it have two mechanisms for pain relief and/or fever reduction?
 * Aspirin shares some side-effects with salicylic acid. Are these due to related chemistry?

The article should be clearer about the differences with salicylic acid, both medically and in its actions. The salicylic acid article could clearly be expanded. Colin°Talk 15:24, 22 September 2007 (UTC)

 * These all are very good points. I do not really know anything about the aspirin pharmacokinetics, e.g. how much of it is decomposed in the body to salicylic acid. I am still not sure how relevant the history of salicylates is to the history of aspirin. Would the history of khat be relevant in bupropion or, even closer, diethylpropion (Tenuate) article? (Diethylpropion is partially metabolized to cathinone, the active principle of khat.) On the other hand, histories of fluoxetine and sertraline do begin with the histories of structurally related compounds. The said fluoxetine and sertraline precursors, however, do not have their own pages. Paul gene 11:22, 23 September 2007 (UTC)

 * And I do not suggest excluding the history of salycilates, I suggest linking to it. The history of aspirin could begin with "Salicylates have been used since antiquity [link to the moved history in the salicylic  acid article]. The French chemist Charles Frederic Gerhardt ....." Then, an introductory sentence would be needed after Kraut and before Hoffmann about the increased medicinal use of salicylic acid in 1870-1900, and how Bayer began working on pro-drugs of salicylic acid to decrease the gastrointestinal side effects. Paul gene 11:37, 23 September 2007 (UTC)

Coughing
Coughing says coughing is a side affect of aspirin? Is this correct on this page? (and if so, why does it cause coughing?) Caffm8 (talk) 19:31, 10 December 2007 (UTC)

History - initial side-effects
Initially aspirin had many problems - shouldn't this be included in the history section? See here, page 456/7. Thoughts? Malick78 (talk) 21:14, 20 January 2008 (UTC)

Reyes syndrome
am i incorrect to say that aspirin is contraindicated in children under the age of 16 according to the BNF not under 12 as stated on this page?

Liamoh (talk) 11:17, 13 March 2008 (UTC)

 * You are correct (BNF 53 (2007)). Fixed. Thanks for pointing it out. - Neparis (talk) 14:48, 13 March 2008 (UTC)

Aspirin in fiction?
I know it's there, i.e. Doctor Who where he says a tablet of aspirin could kill him.

DarkestMoonlight (talk) 15:54, 18 March 2008 (UTC)

Mechanism of action of aspirin article?
An editor has suggested during this article's peer review that the section about aspirin's mechanism of action could potentially be split into it's own article. Personally, I think that with a little more content and a few more sources, this section could indeed stand as it's own article, which would help to shorten Aspirin somewhat by just using a summary. What do other editors think about this idea? CrazyChemGuy (talk) 21:10, 15 April 2008 (UTC)

History section
Paul gene reverted the update of the history section with the explanation: "Replaced unbalanced version of history based on Bayer promotions with the conventional one. Discuss before reverting." ' That version was the intro from history of aspirin, which I think is a fairly balanced and concise overview of the history. It is not based on Bayer promotions, and only coincides with them to the extent that they are accurate. It mentions Bayer in only two sentences, and notes that before academic work in synthesizing aspirin existed before Bayer turned the drug into a world-wide commercial success. Here is that version:

The history of aspirin and the medical use of it and related substances stretches back to antiquity, though pure aspirin (acetylsalicylic acid or ASA) has only been manufactured and marketed since 1899. Medicines made from willow and other salicylate-rich plants date back at least to 3000 BC, and were part of the pharmacopoeia of Western medicine in Classical antiquity and the Middle Ages. Willow bark extract became recognized for its specific effects on fever, pain and inflammation in the mid-eighteenth century. By the nineteenth century pharmacists were experimenting with and prescribing a variety of chemicals related to salicylic acid, the active component of willow extract.

In 1853, chemist Charles Frédéric Gerhardt reacted acetyl chloride with sodium salicylate to produce acetylsalicylic acid for the first time; in the second half of the nineteenth century, other academic chemists established the compound's chemical structure and devised more efficient methods of synthesis. In 1897, scientists at the drug and dye firm Bayer began investigating acetylsalicylic acid as a less-irritating replacement for standard common salicylate medicines. By 1899, Bayer had dubbed this drug Aspirin and was selling it around the world. Aspirin's popularity grew over the first half of the twentieth century, spurred by its effectiveness in the wake of Spanish flu pandemic of 1918, and aspirin's profitability led to fierce competition and the proliferation of aspirin brands and products.

Aspirin's popularity declined after the development of acetaminophen in 1956 and ibuprofen in 1962. In the 1960s and 1970s, John Vane and others discovered the basic mechanism of aspirin's effects, while clinical trials and other studies from the 1960s to the 1980s established aspirin's efficacy as an anti-clotting agent that reduces the risk of clotting diseases. Aspirin sales revived considerably in the last decades of the twentieth century, and remain strong in the twenty-first, thanks to widespread use as a preventive treatment for heart attacks and strokes.

The earlier version was, in my view, extremely unbalanced, focusing almost solely on the synthesis of aspirin and neglecting its broader social, commercial and clinical history. If there are specific suggestions for how the above version is improperly balanced, I'm eager to hear them so that the history of aspirin intro can be improved. I'm resubstituting this material here; let's work to make it an acceptable and broad historical overview.--ragesoss (talk) 18:12, 17 April 2008 (UTC)

 * The problem with the version of Aspirin history Ragesoss is suggesting, is that unfortunately it is based on Bayer promotional materials and more than 100-year-old science. Point-by-point

 * Why mention that Bayer synthesized pure ASA? - because it is in Bayer promotion materials that Bayer was first to do that. Neither German authorities nor the UK courts of the time found any merits in this claim (the US court disagreed). It is generally accepted among chemists that von Gilm and Kraut prepared pure acetylsalycilic acid earlier.
 * Aspirin is less-irritating than salicylic acid or sodium salicylate. - Also a century-old Bayer claim. Is there any contemporary evidence that aspirin is less-irritating than salicylic acid or sodium salicylate?
 * Should other salicylates be mentioned in such detail? Bayer scientists a century ago believed aspirin to be a prodrug of salicylic acid. It is not so, and the mechanism of action of aspirin is different and is due to its acetyl group.
 * It is unfair to chemists to exclude the history of aspirin preparation and determination of its structure in favor of commercial details. Paul Gene (talk) 23:04, 17 April 2008 (UTC)

 * I argued much the same points in September of 2007 (see the Discussion History of that time) and seem to convince the other editors. Thus, you changed a discussed at length and accepted version of the article. Paul Gene (talk) 23:12, 17 April 2008 (UTC)

 * Paul gene, thanks. The secondary sources I've found (in particular, Aspirin Wars by Mann and Plummer and Aspirin by Jeffreys) both claim that aspirin is less irritating.  Is there a more reliable source that claims the contrary?  Neither of these sources is particularly kind to Bayer in general (and both side pretty much accept Eichengrun's account of the Bayer synthesis, contra Bayer's standard legend).  Neither mentions von Gilm; are there secondary sources we can use that confirm vol Gilm's synthesis of pure ASA?  If that is in fact widely accepted, then that section can be reworded; the key thing that Bayer did, after all, was effectively build aspirin's reputation (as a less-irritating salicylate and as a clinically effective drug) and market it effectively, and whether or not they were the first to obtain pure ASA is a secondary concern.  I will try to rework it to address your concerns; a reliable secondary source on von Gilm and non-irritation would be greatly appreciated.--ragesoss (talk) 00:17, 18 April 2008 (UTC)

 * I've revised the second paragraph; hopefully it's more to your liking. It no longer mentions purity, which you are right about being beside the point, and it mentions Gerhardt's work specifically.  It also presents the "less-irritating" bit from the perspective of the Bayer scientists, without definitively claiming that aspirin is in fact less irritating.  The amount of coverage of salicylates is appropriate, in my view; both of the history of aspirin books I mentioned devote a substantial portion of their coverage to the prehistory of aspirin, as do most other sources I've seen.  As for discussion of the business aspects short-changing the chemists, both aspects need to be covered (as well as the research on mechanism and clinical effectiveness, both of which are also crucial aspects of aspirin's history).  The social side of a drug is no less significant than the chemical side, especially a drug that has been used in as many ways as aspirin over such a long period.--ragesoss (talk) 00:34, 18 April 2008 (UTC)

 * Thank you, you revision is very reasonable. Salicylates should be mentioned to provide the background as to why Bayer was looking for their replacement. I just think that it is disproportionately long in this version of the article. The aspirin history is shrouded in many myths and you want to be careful not to trust all the claims in the secondary sources. Jeffries book is particularly full of inventions. Even other, more academic sources, make mistakes. For example, Hippocratic Corpus has no mentions of willow concoctions as a pain killer. This claim appears first in a 1930s review on antique medicine, but I was not able to obtain that source. Paul Gene (talk) 10:37, 18 April 2008 (UTC)

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 * If you write a lot outside of Wikipedia, what kind of writing do you do?

 * Is your writing style influenced by any particular WikiProject or other group on Wikipedia?

At any point during this review, let us know if we recommend any edits, including markup, punctuation and language, that you feel don't fit with your writing style. Thanks for your time. - Dan Dank55 (talk)(mistakes) 04:12, 21 April 2008 (UTC)

Reversion of edit by Paul Gene
I recently made this edit:. I don't think that the source in question is unreliable or that the content needs to be removed- as there is plenty of information out there to support that statement, I think the best course of action if one feels the source given was not reliable would be to find another source and add it. The source may not be scholarly, perhaps, but the opinion that old aspirin smells like vinegar was given by a qualified person with a PhD in the relevant area - their qualifications were listed on the page listed.CrazyChemGuy (talk) 00:12, 30 April 2008 (UTC)

 * The sentence being discussed is this: Formulations containing high concentrations of aspirin often smell like vinegar.  It has the following problems. First, the sentence implies that "high concentrations" of aspirin are somehow special and so lower concentrations would not smell like vinegar, which is strange. Second, references to bulletin boards are generally not considered reliable on WP (see WP:RS), anybody can say that he is a prof and PhD. Third, if you read the bulletin board text, there is nothing about "high concentration formulations", it is about old solid aspirin smelling like vinegar, so it duplicates the next sentence: "aspirin can decompose in moist conditions, yielding salicylic acid and acetic acid. " Perhaps we just should leave this last sentence, which also has a proper quotation. Paul Gene (talk) 01:03, 30 April 2008 (UTC)
 * I would be okay to leave only the last part of that sentence now. I do know that the decomposition of aspirin is autocatylitic and also results in a vinegar odor (I mean, seriously, acetic acid), so I will look for a reliable source- perhaps I'll try the local library for a print source, I haven't found much about it being autocatylitic on google - because I do think that stuff needs to go back in eventually, as it is relevant.  I'll look for things on a few of the other troubled citations too, while I'm there tomorrow anyway. CrazyChemGuy (talk) 02:29, 30 April 2008 (UTC)

 * On a related note, I am removing the following statement: "Another study, however, has reported that the incidence of these side effects, when compared to those of some other forms of aspirin, may be reduced by taking aspirin an enteric coated form. [41] 104 participants were given a 14 day trial on the different types of aspirin being tested. After day 14, the dosage was lowered and reductions in gastric effects were seen in those with the enteric coated aspirin."

 * This statement is completely incorrect. For 14 days the patients were given 75 mg of EC aspirin. And then either continued with the same dose or with increased dose (150 mg) of EC aspirin or with 162 mg of microencapsulated aspirin. Gastric side effects were not measured, so this reference is irrelevant to the topic of side effects. By the way the lit. review part of this paper states "Whilst both enteric coating and buffering agents may theoretically reduce irritation of gastric mucosa, blood levels are just as high as with conventional aspirin and recent work has shown similar rates of bleeding with these preparations" that is the reverse of what it is purported to state. Paul Gene (talk) 01:36, 30 April 2008 (UTC)

False references
A relevant discussion on false references we had with CrazyChemGuy on my talk page:

 * Hi, you have removed several references from Aspirin as being false or not relevant in the way they are cited. I do wonder if on some of them, such as [1], the reference does in fact support the material - even if it is not mentioned in the abstract, the full text of the article may still have information that supports the sentence, could it not? Personally, I have not read the article in question, nor have I read several other of the articles you removed as citations, but do you think maybe one should be a little careful when removing such sourced information? I realize some people do do this, but I doubt that many editors would intentionally introduce sources that are not relevant to the material. I'm not saying you've done anything wrong; I'm just curious if you have double checked all of these references. CrazyChemGuy (talk) 00:05, 30 April 2008 (UTC)

 * I would have checked a full text if it were a well and competently written article. It is not. I checked, however, the full text for the reference you mentioned. And no, the full text does not support that nonsense. 103 out of 160 people had GI symptoms, not 160. In any case this study cannot be used to establish the frequency of GI symptoms that can be specifically attributed to aspirin. To do that it had to be randomized and, ideally, blinded. Second, using citations, which are at best tangential to the material they purport to prove, is a common phenomenon on WP. I would not guess what its causes are. To make everybody's life easier, the WP guidelines generally recommend that in the onus of finding a proof is on the person who inserts information into the article. Cheers, Paul Gene (talk) 00:24, 30 April 2008 (UTC) Paul Gene (talk) 01:41, 30 April 2008 (UTC)

Small Text

Pharmacokinetics
The pH of the small intestine is alkaline, (very), and not acidic. Aspirin is very soluble in the duodenum. Graham Colm Talk 11:29, 27 May 2008 (UTC)
 * You're correct. It seems I screwed that up when I wrote the secton - an IP changed acidity to pH, which is what I meant to type, but I reverted the edit without paying much attention .  Thanks for pointing this error out - I've edited the pharmacokinetics section to fix this error. CrazyChemGuy (talk) 16:59, 27 May 2008 (UTC)

Some medical literature describes ASA use as an ant-inflammatory agent
If this is the case, a specific section should be created and completed.68.97.87.243 (talk) 20:50, 1 December 2013 (UTC)

Lead
Hi, I've noticed the lead mentions the endogenous production of salicylates in the body and while I find it a fascinating tid-bit I do not think it belongs in the lead for two reasons; firstly, from what I've gathered from the article it references it doesn't seem to refer specifically to aspirin as one of the salicylates produced endogenously. Secondly, the article referenced isn't a review article and is hence not a secondary source, consequently it is not one of the preferred sources set forth by WP:MEDMOS. Fuse809 (talk) 17:01, 2 April 2014 (UTC)

The rotating cartoon
…without statement of how it was generated to make clear what it means and how the conformation (pose) appearing was generated—this is simply bad chemistry/science exposition. Please (i) state how the structure generation was performed (in a figure legend, see also next), (ii) check to make sure the conformation has some physical validity (e.g., that it is a physically reasonable MM2, QM, or MD calc-generated representative minimum), and (iii) make sure that the pose is further relevant to one or more article points, and that these are clearly explained (e.g., the near coplanarity of the trio of atoms of the carboxylate group with the aromatic ring says what? the fact that the C1-C2-O-Cacyl dihedral places the acetoxy in a plane nearly orthogonal to the ring says what?).

Otherwise, simply consider removing the cartoon. (A moving molecule untethered to method, physical principle, and a pedagogic point is no more good science than colored vessels on the telley or big screen, with tubes running and gasses bubbling in ways that have nothing to do with acceptable, standard ochem practices. Please!) Le Prof  Leprof 7272 (talk) 04:03, 9 June 2014 (UTC)

storage / shelf-life
Please add information to the article about optimum storage, label expiration dates in various countries, actual potency declination rates and degradation byproducts.

 * articles.mercola.com/sites/articles/archive/2000/04/02/drug-expiration-part-one.aspx.

 * Drugs Frequently Potent Past Expiration
 * By Laurie P. Cohen
 * The Wall Street Journal March 29, 2000

Consider aspirin. Bayer AG puts two-year or three-year dates on aspirin and says that it should be discarded after that. Chris Allen, a vice president at the Bayer unit that makes aspirin, says the dating is "pretty conservative"; when Bayer has tested four-year-old aspirin, it remained 100 percent effective, he says.

So why doesn't Bayer set a four-year expiration date? Because the company often changes packaging, and it undertakes "continuous improvement programs," Mr. Allen says. Each change triggers a need for more expiration-date testing, he says, and testing each time for a four-year life would be impractical.

Bayer has never tested aspirin beyond four years, Mr. Allen says. But Jens Carstensen has. Dr. Carstensen, professor emeritus at the University of Wisconsin's pharmacy school, who wrote what is considered the main text on drug stability, says, "I did a study of different aspirins, and after five years, Bayer was still excellent. Aspirin, if made correctly, is very stable."

 * scopeblog.stanford.edu/2012/10/08/study-expiration-dates-have-nothing-to-do-with-shelf-life-of-drugs/
 * Study: Expiration dates have nothing to do with shelf life of drugs
 * Margarita Gallardo on October 8th, 2012

But a new study published in the Archives of Internal Medicine may get me thinking, “Not so fast!” ... Researchers from the University of California-San Francisco analyzed eight prescription drugs that were between 28 and 40 years beyond the expiration date indicated on the bottle and found that most of the medications retained their potency. CNN.com reports:

Overall, the eight drugs included 14 different active ingredients, including aspirin, codeine and hydrocodone. In 86% of cases, the study found, the amount of active ingredient present in the drugs was at least 90% of the amount indicated on the label.

The study only found that two ingredients – aspirin and amphetamine – consistently fell below the 90% threshold.

-96.233.23.207 (talk) 19:18, 25 July 2014 (UTC)

Chemical data?
There is a huge lack of chemical data, but i dont know how we modify/add it in the banner section. Basic information like the pKa = 3,5 is mentionned in the text but not in the banner section, the place where it should be.

We can see lots of these information on this reliable website(aldrich) : http://www.sigmaaldrich.com/catalog/product/sigma/a5376?lang=en&region=CA Thanks — Preceding unsigned comment added by Graslt95 (talk • contribs) 01:22, 11 November 2014 (UTC)

pronunciation of acetylsalicylic
I'm not familiar with the Wikipedia pronunciation key, so I wish someone who is good with it would fix the pronunciation guide for acetylsalicylic acid. What they have listed is (/əˌsiːtəlˌsælɨˈsɪlɨk/ ə-SEE-təl-SAL-i-SIL-ik) which looks to me like the most common mispronunciation, which sounds like "a cetyl salicylic acid", possibly an incorrect name for "cetyl salicylate."

"Acetylsalicylic" is a compound of "acetyl", pronounced "ass-a-TEEL", and "salicylic", which is shown pronounced correctly. The pronunciation of "acetyl" doesn't change when it is used as a compound with "salicylic," just like it doesn't change when it's used as a compound with morphine in "3-acetylmorphine." Someone please edit the pronunciation guide so that it's the correct way of saying "ass-a-TEEL" -SAL-i-SIL-ik. Thank you. OldOrganicProf (talk) 01:02, 8 June 2015 (UTC) OldOrganicProf

Should trade names be avoided?
A user searching for (for example) Acenterine on Wikipedia will be directed to this article, but will be left in the dark about the relationship between "Acenterine" and aspirin – the search term does not occur in the text of the article. For other drugs it is common practice to give trade names; for example, Zocor redirects to Simvastatin, and that article duly notes that the drug is "marketed under the trade name Zocor". Is there a reason to avoid giving trade names for aspirin in this article? --Lambiam 09:15, 1 July 2015 (UTC)
 * see this: Articles_for_deletion/Panadol and see discussion ongoing Wikipedia_talk:WikiProject_Medicine Jytdog (talk) 12:06, 1 July 2015 (UTC)
 * I find the arguments for avoiding them (like calling them "spammy") weak and don't think this is grounded in policy. I completely agree with the argument put forward by Stuartyeates that users looking for information will know the drugs by the brand names and use these to search Wikipedia.
 * Please note that has been creating redirects from trade names and alternative names to drug articles. Systematically removing this useful information without a solid reason or at least consensus is in my opinion not a good idea.  --Lambiam 22:10, 1 July 2015 (UTC)

 * It's worth noting that redirects and brand name articles can be locked down to various degrees, potentially in bulk. Stuartyeates (talk) 00:52, 2 July 2015 (UTC)
 * There are virtually unlimited variant trade names for some of these drugs. Trying to reliably replicate and maintain all of them in a main space article would be futile. To deal with this, we link to drugbank on each drug infobox. LeadSongDog come howl!  04:46, 2 July 2015 (UTC)
 * Even if the article Catridecacog linked to DrugBank and DrugBank had a page on this drug, it would be of zero help to a user seeking information on NovoThirteen, so this does not address the issue. --Lambiam 09:25, 2 July 2015 (UTC)
 * that is a) a relatively new drug that is b) not generic. nobody is talking about removing brand names from drugs that are still on-patent.  The issue is generics. (I fixed that article a bit, btw) Jytdog (talk) 13:18, 2 July 2015 (UTC)

What is "salicylin" in the lead?
Is it the same as salicylic acid?--李4 (talk) 12:30, 12 August 2015 (UTC)
 * Agree. Unable to find a high quality source and removed. Pubmed has nothing. Doc James  (talk · contribs · email) 13:35, 12 August 2015 (UTC)

 * Someone was evidently reaching for the word salicin. Evidently acetylsalicylic acid, salicylic acid, and salicin are related through metabolism, but which is a metabolite of which and when is more organic chemistry than I am ready for tonight. Quercus solaris (talk) 01:08, 13 August 2015 (UTC)

sourcing
I'm not comfortable with the sourcing in the following content, added in this dif:

In a high quality trial of people suspected of having a major heart attack ("ST-segment Elevation MI"), aspirin saved the life of 1 in 42 by reducing the 30-day death rate from 11.8% to 9.4%. There was no difference in major bleeding (need for blood transfusion or brain bleeding), but there was a small increase in minor bleeding amounting to roughly 1 in every 167 people given aspirin. Thoughts?Jytdog (talk) 06:42, 9 September 2015 (UTC)
 * Yes need to be formatted better. We have this ref that agrees  Doc James  (talk · contribs · email) 07:08, 9 September 2015 (UTC)
 * Not just the formatting. What do you think of that source per MEDRS?  I haven't seen it before. Jytdog (talk) 08:47, 9 September 2015 (UTC)
 * Yes supposedly they are getting them published in a journal going forwards. It is sort of a secondary source. I am on the fence. The conclusions that it is supporting differ little from the other ref I posted. Doc James  (talk · contribs · email) 12:57, 11 September 2015 (UTC)

USPSTF
This is not exactly true: "However, in 2015, the United States Preventive Services Task Force revised its guidelines to recommend aspirin for the goal of reducing the risk of colorectal cancer. "

User:Castncoot the guideline is in draft. That means it is not an official position yet. Here is the time line. Best Doc James  (talk · contribs · email) 18:30, 19 September 2015 (UTC)

Pharmodynamics
"with glucuronic acid it forms salicyl acyl and phenolic glucuronide." why are there two benzene rings in the products while there's only one in the reactants?--李4 (talk) 09:26, 22 August 2015 (UTC)

It's referring to two separate products. Gluconurides with and without the acetyl group are found. The one with the acetyl group is called "salicyl acyl" or "salicylic acyl." The de-acetylated gluconuride, that is, the conjugate with salicylic acid, is called the phenolic gluconuride, because it has an unmasked hydroxyl group. The names are awkward, but it's made clearer in the next paragraph when the metabolites are listed. Roches (talk) 05:41, 10 October 2015 (UTC)

Assessment comment
Substituted at 20:08, 2 May 2016 (UTC)

Dispersible aspirin
Please can someone add an explanation of "dispersible aspirin"; a commonly-available form? The word "dispersible" does not appear in the article at present. I have just redirected Dispersible aspirin to this article. Andy Mabbett ( Pigsonthewing ); Talk to Andy; Andy's edits 16:18, 3 February 2016 (UTC)
 * See and . SpinningSpark 17:36, 3 February 2016 (UTC)

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50 mg vs 75 or 82 mg Baby Aspirin
I searched for literature and it seems like 75/82mg gives the same antiplatelet power as higher doses like 200mg.

But what about 50mg? In some countries 50mg is available.

This study does mention 40mg: https://www.ncbi.nlm.nih.gov/pubmed/1412574

ee1518 (talk) 18:23, 21 April 2016 (UTC)
 * we don't discuss dosing per WP:NOTHOWTO and we don't give medical advice. Also this Talk page is for discussing improvements to the article. Jytdog (talk) 03:24, 22 April 2016 (UTC)

Baby Aspirin and Platelet Count?
If one has a low Platelet Count, is there any cardiovascular benefit of taking Baby Aspirin? If platelet count is high, is baby aspirin highly recommended?

https://en.wikipedia.org/wiki/Platelet#Measurement "The normal range (99% of population analyzed) for platelets in healthy Caucasians is 150,000 to 400,000 per cubic millimeter or 150–400 × 109 per liter. The normal range has been confirmed to be the same in the elderly and Spanish populations. Men as a group have slightly higher mean values than women".

ee1518 (talk) 18:31, 21 April 2016 (UTC)
 * that's a medical question to discuss with a doctor. Jytdog (talk) 03:30, 22 April 2016 (UTC)

Hypothalamic-pituitary-adrenal activity
I removed this section as I found no discussion of this in monographs or reviews (with the exception of a mention in one monograph of a possible effect on TRH tests). Seems UNDUE and the sourcing is not good enough. Thoughts?

Aspirin, like other medications affecting prostaglandin synthesis, has effects on the pituitary gland, which indirectly affects a number of other hormones and physiological functions. Aspirin should not be taken before growth hormone stimulation tests, as pre-treatment with aspirin abolished growth hormone release, but enhanced prolactin release in response to the Arginine growth hormone stimulation test. Additionally, aspirin can lower lower TSH levels (leading to reduced T3 and T4) due to an attenuated TSH release in response to TRH.

Aspirin reduces the effects of vasopressin and increases those of naloxone upon the secretion of ACTH and cortisol by the hypothalamic-pituitary-adrenal axis (HPA axis), which has been suggested to occur through an interaction with endogenous prostaglandins and their role in regulating the HPA axis.

- 11:52, 10 June 2015 Jytdog (according to talk page history)

 * Seems a shame to remove it. What don't you like about the sourcing ? - Rod57 (talk) 20:56, 7 July 2016 (UTC)

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FDA on aspirin
FDA

"The FDA has reviewed the available data and does not believe the evidence supports the general use of aspirin for primary prevention of a heart attack or stroke. In fact, there are serious risks associated with the use of aspirin, including increased risk of bleeding in the stomach and brain, in situations where the benefit of aspirin for primary prevention has not been established."

Is our article strong enough on this. I'll leave this to those dealing with this article but thought this was somewhat stronger wording than our article indicates. I have no further input on this.(Littleolive oil (talk) 14:45, 1 December 2016 (UTC))

Irreversibly blocks platelets
Drilling through the references leads to https://www.ncbi.nlm.nih.gov/pmc/articles/PMC301910/, which states: "Both persist for the life-span of the aspirin-treated platelet." Platelet singular. So platelets in general within one person are suppressed; an individual platelet is blocked. I've edited the article accordingly. As it read before, it could be interpreted as "a dose of aspirin could change platelet function for a subject permanently". Chumpih (talk) 01:10, 11 December 2016 (UTC)

Historical review
10.1111/bjh.14520 JFW | T@lk  12:27, 24 January 2017 (UTC)

Dosage
The caption under the photo in the "Dosage" section says this:

 * The 5-grain aspirin. The usage guidance label on a bottle of aspirin indicates that the dosage is "325 mg (5 gr)".

It says no such thing as far as I can tell. It only says that the tablet contains 325 mg. In fact, under "Dosage" there is no actual mention of dosage. Dynasteria (talk) 11:03, 10 May 2017 (UTC)
 * It says adults should take 1 or 2 tablets. My bottle also contains pills of 325 mg, and says adults should take 1 to 2 tablets. 325 mg is very close to five grains, and the reason 325 mg is used is that traditionally they were five grains. Eric Kvaalen (talk) 13:02, 17 June 2017 (UTC)

Sourcing the fact that aspirin has other mechanisms than acetylating COX
Yesterday I added the sentences "This is not the only mechanism by which aspirin works. Some of its effects are like those of salicylic acid, which does not have the same influence on prostaglandins and thromboxanes because it is not an acetylating agent (see below)." This has now been deleted by User:Jytdog on the grounds that it is "unsourced". Now obviously I could find a source for the fact that there is at least one other mechanism of action (it's mentioned further down in the article), and a source for the fact that aspirin has some effects that are like those of salicylic acid (also mentioned in Wikipedia). But I object to having to support every single sentence with references, even if everybody acknowledges the fact! Eric Kvaalen (talk) 13:02, 17 June 2017 (UTC)
 * Yes sources are not optional; especially after material is challenged. If you care about this please find a MEDRS source and cite it. Thanks. Jytdog (talk) 20:23, 17 June 2017 (UTC)

Aspirin grows on willow trees?
I have twice tried to change the strange claim that aspirin grows on willow trees. The reference makes no such claim. Why is the more accurate statement based on the given reference being reverted? I don't understand. Willow contains the glucoside salicin which is converted to salicylic acid in the body. Willow does not contain a significant amount of acetylsalicylic acid.  D b f i r s   22:25, 15 November 2017 (UTC)
 * OK, I agree to the compromise.   D b f i r s   07:18, 23 November 2017 (UTC)
 * Apologies User:Dbfirs missed your comment here.
 * I am glad the compromise is suitable. Doc James  (talk · contribs · email) 09:27, 23 November 2017 (UTC)

Felix Hoffmann
Per here a number of people were involved and mentioning one in the lead IMO is not appropriate as it is controversial. Should go in the body of the article first.

The term "acetylspiraeic acid" is not in the ref in question? Doc James (talk · contribs · email) 05:51, 4 January 2018 (UTC)

Reyes syndrome and MHRA
I've tagged as needing a better source as to what MHRA does or doesn't recommend re aspirin usage by under 16yr olds. I suspect also that 'recommend' is not right word. MHRA licences medicines with specific indications and usage - better wording, if backed by source, is probably along lines of "In the UK aspirin containing products are not licensed for use by under 16 except where specifically indicated" (one product's SPC mentions Kawasaki’s disease). GraemeLeggett (talk) 17:46, 7 January 2018 (UTC)
 * fixed it.Jytdog (talk) 17:59, 7 January 2018 (UTC)

Change
This text "Aspirin is also used long-term in lower doses to help prevent heart attacks"

Is not really correct. We use 160 mg of ASA post MI. Some people take 325 OD for prevention as it is cheaper than 81mg. Doc James (talk · contribs · email) 02:22, 12 January 2018 (UTC)

IUPAC name hidden
The IUPAC name is hidden. This is the international standard, and whilst I concede that Aspirin is the common name, the IUPAC name should not be "hidden". We shouldn't have to click "show" to see it's IUPAC name, "2-acetoxybenzoic acid". The international community worked very hard to get standardisation with the IUPAC naming system so it should be used :) 132.234.206.221 (talk) 01:07, 31 July 2018 (UTC)
 * I think you might have to go here: Template_talk:Infobox_drug. Bod (talk) 01:39, 31 July 2018 (UTC)

Australian study
I do not have a reliable source for this, but I have heard on the news today (16 September 2018) that an Australian study found that if elderly people took aspirins daily, it was of no benefit in reducing their risk of heart attack. If any one knows the journal in which this study was published, more about this study could go in the article. Vorbee (talk) 19:07, 16 September 2018 (UTC)
 * FWIW - the following text/refs (see copy below) have been added to the "Aspirin" article:

 Copied from the "main page diff (version: 09:34, 17 September 2018)": '''In September 2018, medical researchers concluded, based on a 19,114 person study conducted for five years, that use of low-dose aspirin in older people may not be beneficial and, in some cases, may be harmful. '''

 * Hope this helps in some way - in any case - Enjoy! :) Drbogdan (talk) 01:06, 17 September 2018 (UTC)
 * This is not a newspaper. For pete's sake. Jytdog (talk) 13:47, 17 September 2018 (UTC)
 * i've integrated it. Jytdog (talk) 13:57, 17 September 2018 (UTC)
 * Have adjusted a bit further. Doc James  (talk · contribs · email) 17:03, 17 September 2018 (UTC)

Name origin
It's obvious that the name Aspirin comes from the Greek word "aspro" which means "white", as in white pill. In Australia it was even sold as "Aspro".118.211.253.149 (talk) 08:05, 10 March 2019 (UTC)

 * "Aspro" was a trade name under which aspirin was marketed in the UK. For the etymology of aspirin, the OED says: " German (C. Witthauer 1899, in Die Heilkunde Apr.), shortened form of A cetylirte Spir säure (i.e. acetylated spiræic acid) + -in suffix.".  White pills were on the market long before aspirin was discovered.   Dbfir</i><i style="color: #4a4">s</i>  08:31, 10 March 2019 (UTC)

The etymology should be in the main article.118.211.253.149 (talk) 10:34, 10 March 2019 (UTC)

Short description

 * "Medication used to treat pain, fever, and inflammation"

One of the primary uses is heart disease. Much less so "fever" do to risks in kids. Doc James (talk · contribs · email) 07:12, 30 May 2019 (UTC)

 * Thanks, I have updated this in Wikidata as well. - Wiki-uk (talk) 12:27, 31 May 2019 (UTC)

81 mg dose in the U.S.
It seems strange to see U.S. labeling as "81 mg" when most drug dosages are multiples of 5. The 81 mg is 1/4th of the higher 325 mg dose. What is the reason that the formulation itself is not simply 80 (or 85) mg for marketing purposes? Did that question arise when the low dose was introduced? Who determined the factor of 1/4? Jmar67 (talk) 04:43, 2 June 2019 (UTC)

Extremely dangerous article
The Dosage section sounds from its name as if it will advise readers on what constitutes a safe and effective dosage.

It does neither one.

For that reason, '''this article should have no section labeled "dosage" until such time as someone both a) knowledgeable and b) competent is both willing and able to fill in the missing information.

Otherwise — as is currently the case — readers will come to this article believing that they have read what they need to know about dosage.

But they have not, since the article in its current state says NEITHER what is safe nor what is effective.

Dosage information is too important to be left in the hands of persons who are neither knowledgeable nor competent to write up what they know clearly.128.119.202.110 (talk) 02:30, 8 October 2019 (UTC)

 * The article is careful to avoid recommending any dosage. It reports the sizes of tablets manufactured.  Actual dosage will be as prescribed by a doctor, or as self-administered, following advice on the packet.  Nothing in the article can be taken as advice on dosage.  I agree that Wikipedia should not give such advice, and it doesn't.  If you think the heading is misleading, then perhaps we could change it to dosage units.   <i style="color: blue;">D</i><i style="color: #0cf;">b</i><i style="color: #4fc;">f</i><i style="color: #6f6;">i</i><i style="color: #4e4;">r</i><i style="color: #4a4">s</i>  05:21, 8 October 2019 (UTC)

medical use - heart attacks and strokes subsect.
"It is generally not recommended in people without other health problems, including those over the age of 70. (source: 41)" Double negation in this sentence makes it uncertain what it supposed to convey. aka: clarification needed. Does it try to say that aspirin is used in treatment of people with stroke only if they have some UNSPECIFIED additional health problem except those above 70 years age for they get aspirin without the unspecified additional health problem (because being that old is in itself regarded as a health issue)? 89.134.199.32 (talk) 21:58, 29 December 2019 (UTC).
 * Copyedited the sentence. The AHA guideline here, section 4.6 on aspirin (table summary and section entitled, Recommendation-Specific Supportive Text, part 2) says "there is also no justification for the routine administration of low-dose aspirin for the primary prevention of ASCVD among adults at low estimated ASCVD risk." --Zefr (talk) 23:17, 29 December 2019 (UTC)

Why is this not listed as acetylsalicylic acid?
Aspirin is a brand name, not the name of the drug. At any rate, ASA should at least have its own article... it currently redirects to this. — Preceding unsigned comment added by Theanswertolifetheuniverseandeverything (talk • contribs) 20:51, 22 October 2019 (UTC)
 * It is a generic in much of the world. Doc James  (talk · contribs · email) 14:04, 23 October 2019 (UTC)
 * Aspirin and heroin are genericized trademarks "in much of the world".
 * Aspirin is a trademarked brand name in Germany. Bayer lost or sold their trademark rights to Aspirin in many countries. (1918 and 1921 in US.)
 * The German article Aspirin is a disambiguation page.
 * The German article Acetylsalicylsäure (linked from en:Aspirin) has a hatnote: "Dieser Artikel beschäftigt sich mit dem Wirkstoff Acetylsalicylsäure. Die historischen, ökonomischen und markenrechtlichen Aspekte des Bayer-Aspirins als Medikamentenmarke werden in Aspirin (Marke) beschrieben." - A876 (talk) 08:18, 10 September 2020 (UTC)

section Other adverse effects
had this humongous mistake: microbleeds the size of "5-10 mm". since theres no way a "bleed" in the brain could be called "micro" i deleted the horrendously wrong size indication, but i dont have a source for the correct size so i just left it as "small" as the cited source says. the deleted size indication is probably unsourced (i didnt find in the linked source a size indication, but check it out for yourself) and very likely a typo and instead of mm (millimeter) should have used micrometer. so i deleted the dumb part. probably anyone in the cranial MRI community already knows what size of black dots in the image they used to call microbleeds. if you find a source please add the info to the article. 89.134.199.32 (talk) 10:51, 12 February 2021 (UTC).
 * I reverted your edit because the statement is sourced and that is what the source says. Anyone in the MRI cranial community could offer their opinion, but that would be considered original research and we don't allow that. CV9933 (talk) 12:52, 12 February 2021 (UTC)

move sentence in Prostaglandins and thromboxanes
In the section Prostaglandins and thromboxanes should the sentence

Thromboxanes are responsible for the aggregation of platelets that form blood clots. Heart attacks are caused primarily by blood clots, and low doses of aspirin are seen as an effective medical intervention to prevent a second acute myocardial infarction.[34]

be moved to be part of the previous paragraph? DGerman (talk) 21:39, 6 August 2021 (UTC)

Aspirin as "chemoprotective agent" - incorrect term?
This article uses the term "chemoprotective agent" for aspirin at the top of the 3rd paragraph.

I cannot quickly find any evidence (via the Wikipedia aspirin page or the first Google search results for "aspirin chemotherapy") that aspirin reduces harmful side-effects of chemotherapy, which is what Wikipedia itself gives in its description for "chemoprotective agent". I saw info (on the aforementioned Google search) that aspirin can increase the sensitivity of colorectal cancer and breast cancer to chemo, but this is not the same thing as decreasing the chemo sensitivity of healthy cells. Wikipedia says on the aspirin page that aspirin can prevent (reduce incidence of) cancer, but this is not the same thing either.

I recommend deleting the term "chemoprotective agent" from the beginning of the aspirin article; it has a specific meaning that does not appear to be satisfied by aspirin.

PS: I found a primary source (https://pubmed.ncbi.nlm.nih.gov/22493984/) that does use the term "chemoprotective" to mean "protects against cancer", but this is still inconsistent, at a minimum, with the description given for the term in Wikipedia.

Boatman4 (talk) 18:13, 13 January 2022 (UTC)

 * Thanks, I agree with you and I have removed the term. JimRenge (talk) 18:33, 13 January 2022 (UTC)

Ancient history
There is an interesting story about the discovery of aspirin. There are hundreds of articles, books and programmes about how the ancients used willow bark as a pain killer since ancient times, the implication being that they had essentially discovered aspirin. But this doesn't seem to be true. The German scientists who discovered aspirin weren't even trying to make a new form of painkiller, they were simply trying to make new drugs out of a variety of organic chemicals.

If you look at any old herbal or medical book, it makes no mention of willow bark as a painkiller at all. Instead, the 'ancients' seem to have been quite well-informed, and used burnt willow bark for treating skin disorders, as we use salicylic acid today. But given that no-one ever publishes a book saying "did you know, there isn't really any aspirin in willow bark," this is very hard to reference. So the question is, do we want Wikipedia to report the truth, or the popular myth? How do you approach such an issue? I notice that if I change "Hippocrates used willow as a painkiller" (which is false, as far as I can see) to "Hippocrates doesn't mention willow" (which seems to be true, as you can search the whole of Hippocrates online), I get my change reverted, because an unreferenced claim from a modern journal trumps original research. Any suggestions? E Wusk (talk) 08:51, 2 February 2022 (UTC)
 * WP:VNT. <b style="color:red;">E</b><b style="color:blue;">Eng</b> 09:03, 2 February 2022 (UTC)
 * Yes, that is the issue. There is plenty of verifiability here. If someone makes a claim that Hippocrates wrote something, one can check it. It's far more checkable than, say the results of the recent US election, and Wikipedia goes with the truth there, rather than the far more numerous false claims. Question is, how do you make a decision to go with something that is verifiably true, but not so popular?E Wusk (talk) 09:27, 2 February 2022 (UTC)

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title: Talk:Aspirin/Archive 1