Aspirin: Difference between revisions

| synonyms = {{ubl|2-acetoxybenzoic acid|''o''-acetylsalicylic acid|acetylsalicylic acid|acetyl salicylate|monoacetic acid ester of salicylic acid<ref>{{cite journal|journal=Bulletin of the History of Medicine|title=What's in a Name? Aspirin and the American Medical Association|first=Jan|last vauthors = McTavish J |volume=61|number=3|date=Fall 1987|pages=343–366 |jstor=44442097 |pmid=3311247 |url=https://www.jstor.org/stable/44442097}}</ref>}}

'''Aspirin''', also known as '''acetylsalicylic acid''' ('''ASA'''), is a [[nonsteroidal anti-inflammatory drug]] (NSAID) used to reduce [[pain]], [[fever]], and/or [[inflammation]], and as an [[antithrombotic]].<ref name=AHFS>{{cite web|title=Aspirin|url=https://www.drugs.com/monograph/aspirin.html|via=Drugs.com|publisher=[[American Society of Health-System Pharmacists]]|date=29 November 2021|url-status=live|archive-url=https://web.archive.org/web/20170425142242/https://www.drugs.com/monograph/aspirin.html|archive-date=25 April 2017}}</ref> Specific inflammatory conditions whichthat aspirin is used to treat include [[Kawasaki disease]], [[pericarditis]], and [[rheumatic fever]].<ref name=AHFS/>

A [[Precursor (chemistry)|precursor]] to aspirin found in the bark of the [[willow tree]] (genus ''Salix'') has been used for its health effects for at least 2,400 years.<ref name=Jon2015>{{cite book |vauthors = Jones A |title=Chemistry: An Introduction for Medical and Health Sciences|date=2015|publisher=John Wiley & Sons|isbn=978-0-470-09290-3|pages=5–6|url=https://books.google.com/books?id=ubE0ILq_aDQC&pg=PA6}}</ref><ref>{{cite book |vauthors = Ravina E |title=The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs |date=2011 |publisher=John Wiley & Sons |isbn=978-3-527-32669-3 |page=24 |url=https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA24}}</ref> In 1853, chemist [[Charles Frédéric Gerhardt]] treated the medicine [[sodium salicylate]] with [[acetyl chloride]] to produce acetylsalicylic acid for the first time.<ref name="Jeffreys2008">{{cite book |url=https://books.google.com/books?id=a9gkBwAAQBAJ |title=Aspirin the remarkable story of a wonder drug. |vauthors=Jeffreys D |date=2008 |publisher=Bloomsbury Publishing USA |isbn=978-1-59691-816-0 |archive-url=https://web.archive.org/web/20170908213430/https://books.google.com/books?id=a9gkBwAAQBAJ |archive-date=8 September 2017 |url-status=}}{{rp|46–48}}</ref> Over the next 50 years, other chemists, mostly of the German company [[Bayer]], established the chemical structure and devised more efficient production methods.<ref name=Jeffreys2008/>{{rp|69–75}} [[Felix Hoffmann]] (or [[Arthur Eichengrün]]) of Bayer was the first to produce acetylsalicylic acid in a pure, stable form in 1897.<ref name=HoffmannSHI>{{Cite web |title=Felix Hoffmann |url=https://www.sciencehistory.org/education/scientific-biographies/felix-hoffmann/ |access-date=3 October 2024 |publisher=[[Science History Institute]]}}</ref> By 1899, Bayer had dubbed this drug Aspirin and was selling it globally.<ref name=MannPlummer1991/>{{rp|27}}

Aspirin's popularity grew over the first half of the 20th century, leading to competition between many brands and formulations.<ref name="ACS">{{cite magazine |title=Aspirin |magazine=Chemical & Engineering News |date=20 June 2005 |volume=83 |issue=25 |url=https://pubsapp.acs.org/cen/coverstory/83/8325/8325aspirin.html }}</ref> The word ''Aspirin'' was Bayer's brand name; however, theirits rights to the [[trademark]] were [[Generic trademark|lost or sold in many countries]].<ref name=ACS/> The name is ultimately a blend of the prefix '''a'''(cetyl) + '''spir''' ''[[Spiraea]]'', the meadowsweet plant genus from which the acetylsalicylic acid was originally derived at Bayer + '''-in''', the common chemical suffix.{{Citation needed|date=April 2024}}

Aspirin, an [[acetyl]] derivative of salicylic acid, is a white, crystalline, weakly acidic substance, whichthat melts at {{convert|136|C|F}},<ref name=b92>{{RubberBible92nd|page=3.8}}</ref> and decomposes around {{convert|140|C|F}}.<ref name="Myers2007">{{cite book |vauthors=Myers RL |title=The 100 most important chemical compounds: a reference guide |url=https://books.google.com/books?id=MwpQWcIKMzAC&pg=PA10 |year=2007 |publisher=ABC-CLIO |isbn=978-0-313-33758-1 |page=10 |url-status=live |archive-url=https://web.archive.org/web/20130610170345/http://books.google.com/books?id=MwpQWcIKMzAC&pg=PA10 |archive-date=10 June 2013}}</ref> Its [[acid dissociation constant]] (p''K''_a) is 3.5 at {{convert|25|C|F}}.<ref name="asaaciddissconst">{{cite web |title=Acetylsalicylic acid |publisher=Jinno Laboratory, School of Materials Science, Toyohashi University of Technology |date=4 March 1996 |url=http://chrom.tutms.tut.ac.jp/JINNO/DRUGDATA/07acetylsalicylic_acid.html |access-date=12 April 2014 |url-status=dead |archive-url=https://web.archive.org/web/20120120224558/http://chrom.tutms.tut.ac.jp/JINNO/DRUGDATA/07acetylsalicylic_acid.html |archive-date=20 January 2012}}</ref>

ThereUntil 2005, there was only one proven polymorph of aspirin ('''Form I''' of aspirin), though the existence of another polymorph was debated since the 1960s, and one report from 1981 reported that when crystallized in the presence of aspirin ''anhydride'', the [[diffractogram]] of aspirin has weak additional peaks. Though at the time it was dismissed as mere impurity, it was, in retrospect, '''Form II''' aspirin.<ref name="Bučar-2015">{{cite journal | vauthors = Bučar DK, Lancaster RW, Bernstein J | title = Disappearing polymorphs revisited | journal = Angewandte Chemie | volume = 54 | issue = 24 | pages = 6972–6993 | date = June 2015 | pmid = 26031248 | pmc = 4479028 | doi = 10.1002/anie.201410356 }}</ref>

Medicines made from [[willow]] and other [[salicylate]]-rich plants appear in clay tablets from ancient [[Sumer]] as well as the [[Ebers Papyrus]] from ancient Egypt.<ref name=Jeffreys2008/>{{rp|8–13}}<ref name=ACS/> Hippocrates referred to the use of salicylic tea to reduce fevers around 400 BC, and willow bark preparations were part of the pharmacopoeia of Western medicine in [[classical antiquity]] and the [[Middle Ages]].<ref name=ACS/> Willow bark extract became recognized for its specific effects on fever, pain, and inflammation in the mid-eighteenth century.<ref name="Goldberg">{{cite magazine |vauthors = Goldberg DR |title=Aspirin: Turn of the Century Miracle Drug|url=https://www.sciencehistory.org/distillations/magazine/aspirin-turn-of-the-century-miracle-drug|magazine=Chemical Heritage |date=Summer 2009|volume=27|issue= 2|pages=26–30}}</ref> after the Rev Edward Stone of [[Chipping Norton]], Oxfordshire, noticed that the bitter taste of willow bark resembled the taste of the bark of the [[cinchona]] tree, known as "[[Peruvian bark]]", which was used successfully in [[Peru]] to treat a variety of ailments. Stone experimented with preparations of powdered willow bark on people in Chipping Norton for five years and found it to be as effective as Peruvian bark and a cheaper domestic version. In 1763 he sent a report of his findings to the [[Royal Society]] in London.<ref>{{cite book|title= Aspirin: the Remarkable Story of a Wonder Drug |author= Diarmuid Jeffreys |publisher=Bloomsbury |date=2004 |page=18-34 }}</ref> By the nineteenth century, pharmacists were experimenting with and prescribing a variety of chemicals related to [[salicylic acid]], the active component of willow extract.<ref name="Jeffreys2008" />{{rp|46–55}}

In 1853, chemist [[Charles Frédéric Gerhardt]] treated [[sodium salicylate]] with [[acetyl chloride]] to produce acetylsalicylic acid for the first time;<ref name=Jeffreys2008/>{{rp|46–48}} in the second half of the 19th 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, and identified a new way to synthesize it.<ref name=Jeffreys2008/>{{rp|69–75}} That year, [[Felix Hoffmann]] (or [[Arthur Eichengrün]]) of Bayer was the first to produce acetylsalicylic acid in a pure, stable form.<ref name=HoffmannSHI /> By 1899, Bayer had dubbed this drug Aspirin and was selling it globally.<ref name=MannPlummer1991/>{{rp|27}} The word ''Aspirin'' was Bayer's brand name, rather than the generic name of the drug; however, Bayer's rights to the trademark were lost or sold in many countries. Aspirin's popularity grew over the first half of the 20th century leading to fierce competition with the proliferation of aspirin brands and products.<ref name=ACS/>

Like its ability to control pain, aspirin's ability to control [[fever]] is due to its action on the [[prostaglandin]] system through its irreversible inhibition of [[COX]].<ref>{{cite journal | vauthors = Bartfai T, Conti B | title = Fever | journal = TheScientificWorldJournal | volume = 10 | pages = 490–503 | date = March 2010 | pmid = 20305990 | pmc = 2850202 | doi = 10.1100/tsw.2010.50 | doi-access = free }}</ref> Although aspirin's use as an [[antipyretic]] in adults is well established, many medical societies and regulatory agencies, including the [[American Academy of Family Physicians]], the [[American Academy of Pediatrics]], and the [[Food and Drug Administration]], strongly advise against using aspirin for the treatment of fever in children because of the risk of [[Reye's syndrome]], a rare but often fatal illness associated with the use of aspirin or other salicylates in children during episodes of viral or bacterial infection.<ref>{{cite journal | vauthors = Pugliese A, Beltramo T, Torre D | title = Reye's and Reye's-like syndromes | journal = Cell Biochemistry and Function | volume = 26 | issue = 7 | pages = 741–6 | date = October 2008 | pmid = 18711704 | doi = 10.1002/cbf.1465 | s2cid = 22361194 }}</ref><ref>{{cite journal | vauthors = Beutler AI, Chesnut GT, Mattingly JC, Jamieson B | title = FPIN's Clinical Inquiries. Aspirin use in children for fever or viral syndromes | journal = American Family Physician | volume = 80 | issue = 12 | pages = 1472 | date = December 2009 | pmid = 20000310 }}</ref><ref name=AAPweb>{{cite web|title=Medications Used to Treat Fever|date=29 June 2012 |url=http://www.healthychildren.org/English/health-issues/conditions/fever/Pages/Medications-Used-to-Treat-Fever.aspx|publisher=American Academy of Pediatrics|access-date=25 November 2012|url-status=live|archive-url=https://web.archive.org/web/20130218084054/http://www.healthychildren.org/English/health-issues/conditions/fever/Pages/Medications-Used-to-Treat-Fever.aspx|archive-date=18 February 2013}}</ref> Because of the risk of Reye's syndrome in children, in 1986, the US [[Food and Drug Administration]] (FDA) required labeling on all aspirin-containing medications advising against its use in children and teenagers.<ref name="FDA 1986 FR">{{cite journal|title=51 FR 8180|url=https://www.fda.gov/downloads/Drugs/DevelopmentApprovalProcess/DevelopmentResources/Over-the-CounterOTCDrugs/StatusofOTCRulemakings/UCM078593.pdf|journal=United States Federal Register|volume=51|issue=45|date=7 March 1986|url-status=dead|archive-url=https://web.archive.org/web/20110819130409/https://www.fda.gov/downloads/Drugs/DevelopmentApprovalProcess/DevelopmentResources/Over-the-CounterOTCDrugs/StatusofOTCRulemakings/UCM078593.pdf|archive-date=19 August 2011}}</ref>

There are many anecdotal reportings that aspirin can improve plant's growth and resistance<ref>{{cite web |title=Aspirin Water Helps Plants |url=https://cybercemetery.unt.edu/archive/allcollections/20090117082434/http://www.plantea.com/plant-aspirin.htm |access-date= |website=cybercemetery.unt.edu}}</ref><ref>{{cite web |title=Gardens: drug therapy for plants {{!}} Gardening advice |url=https://amp.theguardian.com/lifeandstyle/2016/jan/31/drug-therapy-for-plants |access-date= |website=[[The Guardian]]|date=31 January 2016 }}</ref> though most research involved [[salicylic acid]] instead of aspirin.<ref>{{cite web |title=Priming Plant Defenses with Aspirin-like Compound : USDA ARS |url=https://www.ars.usda.gov/news-events/news/research-news/2014/priming-plant-defenses-with-aspirin-like-compound/ |access-date= |website=www.ars.usda.gov}}</ref>