Talk:Aspirin

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Contents 1 Aspirin is a BRAND. It has copyright. 2 List of countries that have rejected Aspirin as a registered trademark 3 Added an image 4 Methylsalicylic acid 5 Action of salicylic acid? 6 Boiling point/decomposition 7 Test for ASA 8 SMILES 9 The name 10 Section called "Aspirin" 11 Aspirin and Cancer 12 Molecular Structure 13 Menstruating women? 14 Fatal cases 15 Picric Acid 16 Pronunciation

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)

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

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

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

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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.

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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

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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

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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:Wikipedia medicine standards - please use this in stead of any other text. --

snoyes 18:55 Feb 20, 2003 (UTC)

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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)

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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.

[edit] 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 Wikipedia: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)

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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!

[edit] 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.

[edit] 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.

[edit] 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)

[edit] 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)

[edit] 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 : [1] Edgar181 01:07, 21 January 2006 (UTC)

[edit] Test for ASA

There was a standing request in the natural sciences portion of Wikipedia:Requested_articles/Natural_Sciences#Chemical_compounds. 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)

[edit] SMILES

The current SMILES string used in this artice is CC(=O)OC1=CC=CC=C1C(=O)O. 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 CC(=O)c1ccccc1(C(=O)O) 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)

[edit] 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).

[edit] 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)

[edit] 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)

[edit] 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)

[edit] 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: [2] [3]

[4] [5] [6] Ksheka 12:51, 24 October 2006 (UTC)

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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)

[edit] 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)

[edit] 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)

[edit] 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? IPA: [əˈsɛtlˌsæləˈsɪlɪk ˈæsɪd] 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).