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{{distinguish|Robert Asprin}}
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{{Infobox drug
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| NIAID_ChemDB =
| PDB_ligand = AIN
| 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| 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>}}
<!-- Chemical and physical data -->
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}}
'''Aspirin''', also known as '''acetylsalicylic acid''' ('''ASA'''), is a [[nonsteroidal anti-inflammatory drug]] (NSAID) used to reduce [[pain]], [[fever]], and
Aspirin is also used long-term to help prevent further [[heart attacks]], [[ischaemic stroke]]s, and [[thrombus|blood clots]] in people at high risk.<ref name=AHFS/> For pain or fever, effects typically begin within 30 minutes.<ref name=AHFS/> Aspirin works similarly to other NSAIDs but also suppresses the normal functioning of [[platelet]]s.<ref name=AHFS/>
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One common [[adverse effect]] is an [[upset stomach]].<ref name=AHFS/> More significant side effects include [[stomach ulcer]]s, [[stomach bleeding]], and worsening [[asthma]].<ref name=AHFS/> Bleeding risk is greater among those who are older, drink [[Alcohol (drug)|alcohol]], take other NSAIDs, or are on other [[anticoagulant|blood thinners]].<ref name=AHFS/> Aspirin is not recommended in the last part of [[pregnancy]].<ref name=AHFS/> It is not generally recommended in children with [[infection]]s because of the risk of [[Reye syndrome]].<ref name=AHFS/> High doses may result in [[tinnitus|ringing in the ears]].<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 is available [[Over-the-counter drug|without medical prescription]] as a proprietary or [[generic medication]]<ref name=AHFS/> in most jurisdictions. It is one of the most widely used medications globally, with an estimated {{convert|40000|tonne}} (50 to 120 billion [[Tablet (pharmacy)|pills]])
==Brand vs. generic name==
In 1897, scientists at the [[Bayer]] company began studying acetylsalicylic acid as a less-irritating replacement medication for common salicylate medicines.<ref name=Jeffreys2008/>{{rp|69–75}}<ref name="Distillations">{{cite magazine | vauthors = Dick B |title=Hard Work and Happenstance |url=https://www.sciencehistory.org/distillations/magazine/hard-work-and-happenstance |magazine=Distillations |publisher=[[Science History Institute]] |date=2018 |volume=4 |issue=1 |pages=44–45 }}</ref> By 1899, Bayer had named it "Aspirin" and
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,
==Chemical properties==
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==Physical properties==
Aspirin, an [[acetyl]] derivative of salicylic acid, is a white, crystalline, weakly acidic substance
===Polymorphism===
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[[Polymorphism (materials science)|Polymorphism]], or the ability of a substance to form more than one [[crystal structure]], is important in the development of pharmaceutical ingredients. Many drugs receive regulatory approval for only a single crystal form or polymorph.
'''Form II''' was reported in 2005,<ref>{{cite journal | vauthors = Vishweshwar P, McMahon JA, Oliveira M, Peterson ML, Zaworotko MJ | title = The predictably elusive form II of aspirin | journal = Journal of the American Chemical Society | volume = 127 | issue = 48 | pages = 16802–16803 | date = December 2005 | pmid = 16316223 | doi = 10.1021/ja056455b
In form I, pairs of aspirin molecules form centrosymmetric [[Dimer (chemistry)|dimers]] through the [[acetyl]] groups with the (acidic) [[methyl]] proton to [[carbonyl]] [[hydrogen bond]]s. In form II, each aspirin molecule forms the same hydrogen bonds, but with two neighbouring molecules instead of one. With respect to the hydrogen bonds formed by the [[carboxylic acid]] groups, both polymorphs form identical dimer structures. The aspirin polymorphs contain identical 2-dimensional sections and are therefore more precisely described as polytypes.<ref>{{cite web |title=Polytypism - Online Dictionary of Crystallography |url=http://reference.iucr.org/dictionary/Polytypism |website=reference.iucr.org}}</ref>
Pure Form II aspirin could be prepared by seeding the batch with aspirin anhydrate in 15% weight.<ref name="Bučar-2015" />
Form III was reported in 2015 by compressing form I above 2 GPa, but it reverts back to Form I when pressure is removed.<ref>{{Cite journal | vauthors = Crowell EL, Dreger ZA, Gupta YM |date=2015-02-15 |title=High-pressure polymorphism of acetylsalicylic acid (aspirin): Raman spectroscopy |url=https://www.sciencedirect.com/science/article/abs/pii/S0022286014011065 |journal=Journal of Molecular Structure |volume=1082 |pages=29–37 |doi=10.1016/j.molstruc.2014.10.079 |issn=0022-2860}}</ref> Form IV was reported in 2017. It is stable at ambient conditions.<ref>{{Cite journal | vauthors = Shtukenberg AG, Hu CT, Zhu Q, Schmidt MU, Xu W, Tan M, Kahr B |date=2017-06-07 |title=The Third Ambient Aspirin Polymorph |url=https://pubs.acs.org/doi/10.1021/acs.cgd.7b00673 |journal=Crystal Growth & Design |language=en |volume=17 |issue=6 |pages=3562–3566 |doi=10.1021/acs.cgd.7b00673 |issn=1528-7483}}</ref>
==Mechanism of action==
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===Prostaglandins and thromboxanes===
Aspirin's ability to suppress the production of prostaglandins and thromboxanes is due to its irreversible inactivation of the [[cyclooxygenase]] (COX; officially known as prostaglandin-endoperoxide synthase, PTGS) enzyme required for prostaglandin and thromboxane synthesis. Aspirin acts as an acetylating agent where an acetyl group is covalently attached to a [[serine]] residue in the active site of the
Low-dose aspirin use irreversibly blocks the formation of [[thromboxane A2|thromboxane A<sub>2</sub>]] in platelets, producing an inhibitory effect on platelet aggregation during the lifetime of the affected platelet (8–9 days). This antithrombotic property makes aspirin useful for reducing the incidence of heart attacks in people who have had a heart attack, unstable angina, ischemic stroke or transient ischemic attack.<ref>{{cite web |url=http://www.americanheart.org/presenter.jhtml?identifier=4456 |title=Aspirin in heart attack and stroke prevention |access-date=8 May 2008 |publisher=American Heart Association |archive-url=https://web.archive.org/web/20080331031146/http://www.americanheart.org/presenter.jhtml?identifier=4456 |archive-date=31 March 2008 }}</ref> 40{{nbsp}}mg of aspirin a day is able to inhibit a large proportion of maximum thromboxane A<sub>2</sub> release provoked acutely, with the prostaglandin
Prostaglandins, local [[hormone]]s produced in the body, have diverse effects, including the transmission of pain information to the brain, modulation of the [[hypothalamus|hypothalamic]] thermostat, and inflammation. Thromboxanes are responsible for the aggregation of platelets that form [[clot|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.<ref name="pmid19482214">{{cite journal |vauthors=Baigent C, Blackwell L, Collins R, Emberson J, Godwin J, Peto R, Buring J, Hennekens C, Kearney P, Meade T, Patrono C, Roncaglioni MC, Zanchetti A |date=May 2009 |title=Aspirin in the primary and secondary prevention of vascular disease: collaborative meta-analysis of individual participant data from randomised trials |journal=Lancet |volume=373 |issue=9678 |pages=1849–60 |doi=10.1016/S0140-6736(09)60503-1 |pmc=2715005 |pmid=19482214}}</ref>
===COX-1 and COX-2 inhibition===
At least two different types of [[cyclooxygenase]]s, [[COX-1]] and [[COX-2]], are acted on by aspirin. Aspirin irreversibly inhibits COX-1 and modifies the enzymatic activity of COX-2. COX-2 normally produces [[prostanoid]]s, most of which are proinflammatory. Aspirin-modified
Several COX-2 inhibitors, such as [[rofecoxib]] (Vioxx), have been withdrawn from the market, after evidence emerged that
Furthermore, aspirin, while inhibiting the ability of COX-2 to form pro-inflammatory products such as the [[prostaglandins]], converts this enzyme's activity from a prostaglandin-forming cyclooxygenase to a [[lipoxygenase]]-like enzyme: aspirin-treated COX-2 metabolizes a variety of [[polyunsaturated fatty acids]] to hydroperoxy products which are then further metabolized to [[specialized proresolving mediators]] such as the aspirin-triggered [[lipoxin]]s, aspirin-triggered [[resolvins]], and aspirin-triggered [[maresin]]s. These mediators possess potent anti-inflammatory activity. It is proposed that this aspirin-triggered transition of COX-2 from cyclooxygenase to lipoxygenase activity and the consequential formation of specialized proresolving mediators contributes to the anti-inflammatory effects of aspirin.<ref name="pmid25895638">{{cite journal | vauthors = Romano M, Cianci E, Simiele F, Recchiuti A | title = Lipoxins and aspirin-triggered lipoxins in resolution of inflammation | journal = European Journal of Pharmacology | volume = 760 | pages = 49–63 | date = August 2015 | pmid = 25895638 | doi = 10.1016/j.ejphar.2015.03.083 }}</ref><ref name="pmid23747022">{{cite journal | vauthors = Serhan CN, Chiang N | title = Resolution phase lipid mediators of inflammation: agonists of resolution | journal = Current Opinion in Pharmacology | volume = 13 | issue = 4 | pages = 632–40 | date = August 2013 | pmid = 23747022 | pmc = 3732499 | doi = 10.1016/j.coph.2013.05.012 }}</ref><ref name="pmid26546723">{{cite journal | vauthors = Weylandt KH | title = Docosapentaenoic acid derived metabolites and mediators - The new world of lipid mediator medicine in a nutshell | journal = European Journal of Pharmacology | volume = 785 | pages = 108–115 | date = August 2016 | pmid = 26546723 | doi = 10.1016/j.ejphar.2015.11.002 }}</ref>
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[[File:Aspirine-1923.jpg|thumb|left|1923 advertisement]]
<!-- DO NOT PUT NEW CONTENT HERE. PLEASE UPDATE THE BODY OF [[HISTORY OF ASPIRIN]] AND UPDATE THE LEAD, AND COPY THAT LEAD HERE -->
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
[[File:Old Package of Aspirin.jpg|thumb|Old package. "Export from Germany is prohibited"]]
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/>
Aspirin's popularity declined after the development of [[paracetamol|acetaminophen/paracetamol]] in 1956 and [[ibuprofen]] in 1962. In the 1960s and 1970s, [[John Vane]] and others discovered the basic mechanism of aspirin's effects,<ref name=Jeffreys2008/>{{rp|226–231}} 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.<ref name=Jeffreys2008/>{{rp|247–257}} The initial large studies on the use of low-dose aspirin to prevent heart attacks that were published in the 1970s and 1980s helped spur reform in [[clinical research ethics]] and [[guidelines for human subject research]] and US federal law, and are often cited as examples of clinical trials that included only men, but from which people drew general conclusions that did not hold true for women.<ref>{{cite journal | vauthors = Schiebinger L | title = Women's health and clinical trials | journal = The Journal of Clinical Investigation | volume = 112 | issue = 7 | pages = 973–7 | date = October 2003 | pmid = 14523031 | pmc = 198535 | doi = 10.1172/JCI19993 }}</ref><ref>{{cite journal | vauthors = | title = Regular aspirin intake and acute myocardial infarction | journal = British Medical Journal | volume = 1 | issue = 5905 | pages = 440–3 | date = March 1974 | pmid = 4816857 | pmc = 1633212 | doi = 10.1136/bmj.1.5905.440 }}</ref><ref>{{cite journal | vauthors = Elwood PC, Cochrane AL, Burr ML, Sweetnam PM, Williams G, Welsby E, Hughes SJ, Renton R | title = A randomized controlled trial of acetyl salicylic acid in the secondary prevention of mortality from myocardial infarction | journal = British Medical Journal | volume = 1 | issue = 5905 | pages = 436–40 | date = March 1974 | pmid = 4593555 | pmc = 1633246 | doi = 10.1136/bmj.1.5905.436 }}</ref>
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==Medical use==
Aspirin is used in the treatment of a number of conditions, including fever, pain, [[rheumatic fever]], and inflammatory conditions, such as [[rheumatoid arthritis]], [[pericarditis]], and [[Kawasaki disease]].<ref name=AHFS/> Lower doses of aspirin have also been shown to reduce the risk of death from a [[myocardial infarction|heart attack]], or the risk of [[stroke]] in people who are at high risk or who have cardiovascular disease, but not in elderly people who are otherwise healthy.<ref name="USFDA-patient-guideline">{{citation-attribution|1={{cite web |title=Aspirin for reducing your risk of heart attack and stroke: know the facts |url=https://www.fda.gov/drugs/safe-daily-use-aspirin/aspirin-reducing-your-risk-heart-attack-and-stroke-know-facts |publisher=U.S. [[Food and Drug Administration]] (FDA) |access-date=26 July 2012 |url-status=live |archive-url=https://web.archive.org/web/20120814182151/https://www.fda.gov/Drugs/ResourcesForYou/Consumers/BuyingUsingMedicineSafely/UnderstandingOver-the-CounterMedicines/SafeDailyUseofAspirin/ucm291433.htm |archive-date=14 August 2012}} }}</ref><ref name="USPSTF-CV">{{citation-attribution|1={{cite web |title=Aspirin for the prevention of cardiovascular disease |url=http://www.uspreventiveservicestaskforce.org/uspstf/uspsasmi.htm |publisher=[[U.S. Preventive Services Task Force]] |access-date=26 July 2012 |url-status=dead |archive-url=https://web.archive.org/web/20120711031337/http://www.uspreventiveservicestaskforce.org/uspstf/uspsasmi.htm |archive-date=11 July 2012}} }}</ref><ref>{{cite journal | vauthors = Seshasai SR, Wijesuriya S, Sivakumaran R, Nethercott S, Erqou S, Sattar N, Ray KK | title = Effect of aspirin on vascular and nonvascular outcomes: meta-analysis of randomized controlled trials | journal = Archives of Internal Medicine | volume = 172 | issue = 3 | pages = 209–16 | date = February 2012 | pmid = 22231610 | doi = 10.1001/archinternmed.2011.628 | hdl-access = free | doi-access = free | hdl = 10044/1/34287 | title-link = doi }}</ref><ref name="NEJM-20180916">{{cite journal | vauthors = McNeil JJ, Woods RL, Nelson MR, Reid CM, Kirpach B, Wolfe R, Storey E, Shah RC, Lockery JE, Tonkin AM, Newman AB, Williamson JD, Margolis KL, Ernst ME, Abhayaratna WP, Stocks N, Fitzgerald SM, Orchard SG, Trevaks RE, Beilin LJ, Donnan GA, Gibbs P, Johnston CI, Ryan J, Radziszewska B, Grimm R, Murray AM | title = Effect of Aspirin on Disability-free Survival in the Healthy Elderly | journal = The New England Journal of Medicine | volume = 379 | issue = 16 | pages = 1499–1508 | date = October 2018 | pmid = 30221596 | pmc = 6426126 | doi = 10.1056/NEJMoa1800722 | hdl-access = free | doi-access = free | hdl = 1885/154654 | title-link = doi }}</ref><ref name=NEJM2018CVE>{{cite journal | vauthors = McNeil JJ, Wolfe R, Woods RL, Tonkin AM, Donnan GA, Nelson MR, Reid CM, Lockery JE, Kirpach B, Storey E, Shah RC, Williamson JD, Margolis KL, Ernst ME, Abhayaratna WP, Stocks N, Fitzgerald SM, Orchard SG, Trevaks RE, Beilin LJ, Johnston CI, Ryan J, Radziszewska B, Jelinek M, Malik M, Eaton CB, Brauer D, Cloud G, Wood EM, Mahady SE, Satterfield S, Grimm R, Murray AM | title = Effect of Aspirin on Cardiovascular Events and Bleeding in the Healthy Elderly | journal = The New England Journal of Medicine | volume = 379 | issue = 16 | pages = 1509–1518 | date = October 2018 | pmid = 30221597 | pmc = 6289056 | doi = 10.1056/NEJMoa1805819 | doi-access = free | title-link = doi }}</ref> There is evidence that aspirin is effective at preventing [[colorectal cancer]], though the mechanisms of this effect are unclear.<ref name="Algra 518–27">{{cite journal | vauthors = Algra AM, Rothwell PM | title = Effects of regular aspirin on long-term cancer incidence and metastasis: a systematic comparison of evidence from observational studies versus randomised trials | journal = The Lancet. Oncology | volume = 13 | issue = 5 | pages = 518–27 | date = May 2012 | pmid = 22440112 | doi = 10.1016/S1470-2045(12)70112-2
===Pain===
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===Fever===
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>
===Inflammation===
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*{{lay source |template = cite news|vauthors = Thomas K|url= https://www.nytimes.com/2012/12/05/business/coating-on-buffered-aspirin-may-hide-its-heart-protective-effects.html|title = Study Raises Questions on Coating of Aspirin|date = 4 December 2012|website = [[The New York Times]] }}</ref>
Meta-analysis and systematic reviews have concluded that laboratory confirmed aspirin resistance confers increased rates of poorer outcomes in cardiovascular and neurovascular diseases.<ref>{{cite journal | vauthors = Li J, Song M, Jian Z, Guo W, Chen G, Jiang G, Wang J, Wu X, Huang L | title = Laboratory aspirin resistance and the risk of major adverse cardiovascular events in patients with coronary heart disease on confirmed aspirin adherence | journal = Journal of Atherosclerosis and Thrombosis | volume = 21 | issue = 3 | pages = 239–47 | date = 2014 | pmid = 24201035 | doi = 10.5551/jat.19521 | doi-access = free | title-link = doi }}</ref><ref name="pmid18202034"/><ref>{{cite journal | vauthors = Sofi F, Marcucci R, Gori AM, Abbate R, Gensini GF | title = Residual platelet reactivity on aspirin therapy and recurrent cardiovascular events--a meta-analysis | journal = International Journal of Cardiology | volume = 128 | issue = 2 | pages = 166–71 | date = August 2008 | pmid = 18242733 | doi = 10.1016/j.ijcard.2007.12.010 | hdl-access = free | hdl = 2158/323452 }}</ref><ref>{{cite journal | vauthors = Shim EJ, Ryu CW, Park S, Lee HN, Shin HS, Kim SB | title = Relationship between adverse events and antiplatelet drug resistance in neurovascular intervention: a meta-analysis | journal = Journal of NeuroInterventional Surgery | volume = 10 | issue = 10 | pages = 942–948 | date = October 2018 | pmid = 29352056 | doi = 10.1136/neurintsurg-2017-013632 | s2cid = 38147668 }}</ref><ref>{{cite journal | vauthors = Fiolaki A, Katsanos AH, Kyritsis AP, Papadaki S, Kosmidou M, Moschonas IC, Tselepis AD, Giannopoulos S | title = High on treatment platelet reactivity to aspirin and clopidogrel in ischemic stroke: A systematic review and meta-analysis | journal = Journal of the Neurological Sciences | volume = 376 | pages = 112–116 | date = May 2017 | pmid = 28431593 | doi = 10.1016/j.jns.2017.03.010 | s2cid = 3485236 }}</ref><ref>{{cite journal | vauthors = Snoep JD, Hovens MM, Eikenboom JC, van der Bom JG, Huisman MV | title = Association of laboratory-defined aspirin resistance with a higher risk of recurrent cardiovascular events: a systematic review and meta-analysis | journal = Archives of Internal Medicine | volume = 167 | issue = 15 | pages = 1593–9 | date = 13 August 2007 | pmid = 17698681 | doi = 10.1001/archinte.167.15.1593 | doi-access = free | title-link = doi }}</ref> Although the majority of research conducted has surrounded cardiovascular and neurovascular, there is emerging research into the risk of aspirin resistance after orthopaedic surgery where aspirin is used for venous thromboembolism prophylaxis.<ref name="A Narrative Review of Aspirin Resis">{{cite journal | vauthors = van Oosterom N, Barras M, Bird R, Nusem I, Cottrell N | title = A Narrative Review of Aspirin Resistance in VTE Prophylaxis for Orthopaedic Surgery | journal = Drugs | volume = 80 | issue = 18 | pages = 1889–1899 | date = December 2020 | pmid = 33037568 | doi = 10.1007/s40265-020-01413-w | s2cid = 222234431 }}</ref> Aspirin resistance in orthopaedic surgery, specifically after total hip and knee arthroplasties, is of interest as risk factors for aspirin resistance are also risk factors for venous thromboembolisms and osteoarthritis; the
== Dosages ==
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===Gastrointestinal===
Aspirin increases the risk of [[upper gastrointestinal bleeding]].<ref name="Sorensen 2000">{{cite journal | vauthors = Sørensen HT, Mellemkjaer L, Blot WJ, Nielsen GL, Steffensen FH, McLaughlin JK, Olsen JH | title = Risk of upper gastrointestinal bleeding associated with use of low-dose aspirin | journal = The American Journal of Gastroenterology | volume = 95 | issue = 9 | pages = 2218–2224 | date = September 2000 | pmid = 11007221 | doi = 10.1016/s0002-9270(00)01040-6 }}</ref> Enteric coating on aspirin
Blockade of COX-1 by aspirin apparently results in the upregulation of COX-2 as part of a gastric defense.<ref>{{cite journal |vauthors = Wallace JL |title = Prostaglandins, NSAIDs, and gastric mucosal protection: why doesn't the stomach digest itself? |journal = Physiological Reviews |volume = 88 |issue = 4 |pages = 1547–65 |date = October 2008 |pmid = 18923189 |doi = 10.1152/physrev.00004.2008 |s2cid = 448875 }}</ref>
"[[Buffer solution|Buffering]]" is an additional method
Taking
===Retinal vein occlusion===
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===Reye's syndrome===
{{Main|Reye's syndrome}}
Reye's syndrome, a rare but severe illness characterized by acute [[encephalopathy]] and [[fatty liver]], can occur when children or adolescents are given aspirin for a fever or other illness or infection. From 1981 to 1997, 1207 cases of Reye's syndrome in people younger than 18 were reported to the US [[Centers for Disease Control and Prevention]] (CDC). Of these, 93% reported being ill in the three weeks preceding the onset of Reye's syndrome, most commonly with a [[Respiratory tract infection|respiratory infection]], [[chickenpox]], or [[diarrhea]]. Salicylates were detectable in 81.9% of children for whom test results were reported.<ref name=Belay>{{cite journal |vauthors = Belay ED, Bresee JS, Holman RC, Khan AS, Shahriari A, Schonberger LB |title = Reye's syndrome in the United States from 1981 through 1997 |journal = The New England Journal of Medicine |volume = 340 |issue = 18 |pages = 1377–82 |date = May 1999 |pmid = 10228187 |doi = 10.1056/NEJM199905063401801 |doi-access = free }}</ref> After the association between Reye's syndrome and aspirin was reported, and safety measures to prevent it (including a [[Surgeon General of the United States|Surgeon General]]'s warning, and changes to the labeling of aspirin-containing drugs) were implemented, aspirin taken by children declined considerably in the United States, as did the number of reported cases of Reye's syndrome; a similar decline was found in the United Kingdom after warnings against pediatric aspirin use were issued.<ref name=Belay/> The US [[Food and Drug Administration]] recommends aspirin (or aspirin-containing products) should not be given to anyone under the age of 12 who has a fever,<ref name="BMJ2002-Macdonald"/> and the UK [[National Health Service]] recommends children who are under 16 years of age should not take aspirin, unless it is on the advice of a doctor.<ref>{{cite web |url=
===Skin===
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Aspirin can induce [[angioedema|swelling of skin tissues]] in some people. In one study, [[angioedema]] appeared one to six hours after ingesting aspirin in some of the people. However, when the aspirin was taken alone, it did not cause angioedema in these people; the aspirin had been taken in combination with another NSAID-induced drug when angioedema appeared.<ref>{{cite journal |vauthors = Berges-Gimeno MP, Stevenson DD |title = Nonsteroidal anti-inflammatory drug-induced reactions and desensitization |journal = The Journal of Asthma |volume = 41 |issue = 4 |pages = 375–84 |date = June 2004 |pmid = 15281324 |doi = 10.1081/JAS-120037650 |s2cid = 29909460 }}</ref>
Aspirin causes an increased risk of cerebral microbleeds, having the appearance on [[MRI]] scans of 5 to 10{{nbsp}}mm or smaller, hypointense (dark holes) patches.<ref>{{cite journal |vauthors = Vernooij MW, Haag MD, van der Lugt A, Hofman A, Krestin GP, Stricker BH, Breteler MM |title = Use of antithrombotic drugs and the presence of cerebral microbleeds: the Rotterdam Scan Study |journal = Archives of Neurology |volume = 66 |issue = 6 |pages = 714–20 | date = June 2009 |pmid = 19364926 |doi = 10.1001/archneurol.2009.42 |doi-access = free | title-link = doi }}</ref><ref>{{cite journal |vauthors = Gorelick PB |title = Cerebral microbleeds: evidence of heightened risk associated with aspirin use |journal = Archives of Neurology |volume = 66 |issue = 6 |pages = 691–3 |date = June 2009 |pmid = 19506128 |doi = 10.1001/archneurol.2009.85 }}</ref>
A study of a group with a mean dosage of aspirin of 270{{nbsp}}mg per day estimated an average absolute risk increase in [[intracerebral hemorrhage]] (ICH) of 12 events per 10,000 persons.<ref name=He1998/> In comparison, the estimated absolute risk reduction in myocardial infarction was 137 events per 10,000 persons, and a reduction of 39 events per 10,000 persons in ischemic stroke.<ref name=He1998>{{cite journal |vauthors = He J, Whelton PK, Vu B, Klag MJ |title = Aspirin and risk of hemorrhagic stroke: a meta-analysis of randomized controlled trials |journal = JAMA |volume = 280 |issue = 22 |pages = 1930–5 |date = December 1998 |pmid = 9851479 |doi = 10.1001/jama.280.22.1930 |s2cid = 22997730 }}</ref> In cases where ICH already has occurred, aspirin use results in higher mortality, with a dose of about 250{{nbsp}}mg per day resulting in a [[relative risk]] of death within three months after the ICH around 2.5 (95% [[confidence interval]] 1.3 to 4.6).<ref name=Saloheimo2006>{{cite journal |vauthors = Saloheimo P, Ahonen M, Juvela S, Pyhtinen J, Savolainen ER, Hillbom M |title = Regular aspirin-use preceding the onset of primary intracerebral hemorrhage is an independent predictor for death |journal = Stroke |volume = 37 |issue = 1 |pages = 129–33 |date = January 2006 |pmid = 16322483 |doi = 10.1161/01.STR.0000196991.03618.31 |doi-access = free | title-link = doi }}</ref>
Aspirin and other NSAIDs can cause [[hyperkalemia|abnormally high blood levels of potassium]] by inducing a [[hyporeninemic hypoaldosteronism|hyporeninemic
Use of low-dose aspirin before a surgical procedure has been associated with an increased risk of bleeding events in some patients, however, ceasing aspirin prior to surgery has also been associated with an increase in major adverse cardiac events. An analysis of multiple studies found a three-fold increase in adverse events such as [[myocardial infarction]] in patients who ceased aspirin prior to surgery. The analysis found that the risk is dependent on the type of surgery being performed and the patient indication for aspirin use.<ref>{{cite journal | vauthors = Biondi-Zoccai GG, Lotrionte M, Agostoni P, Abbate A, Fusaro M, Burzotta F, Testa L, Sheiban I, Sangiorgi G | title = A systematic review and meta-analysis on the hazards of discontinuing or not adhering to aspirin among 50,279 patients at risk for coronary artery disease | journal = European Heart Journal | volume = 27 | issue = 22 | pages = 2667–2674 | date = November 2006 | pmid = 17053008 | doi = 10.1093/eurheartj/ehl334 }}</ref>
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=== In gardening ===
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== Veterinary medicine ==
Aspirin is sometimes used in veterinary medicine as an [[anticoagulant]] or to [[analgesic|relieve pain]] associated with musculoskeletal inflammation or [[osteoarthritis]]. Aspirin should
Dogs are better able to tolerate aspirin than cats are.<ref name="Merck" /> Cats metabolize aspirin slowly because they lack the [[glucuronide]] conjugates that aid in the excretion of aspirin, making it potentially toxic if dosing is not spaced out properly.<ref name="Edwards-2016" /><ref>{{cite book|title=Feline internal medicine secrets|publisher=Hanley & Belfus|year=2001|isbn=978-1-56053-461-7 |veditors = Lappin MR |location=Philadelphia|page=160}}</ref> No clinical signs of toxicosis occurred when cats were given 25{{nbsp}}mg/kg of aspirin every 48 hours for 4 weeks,<ref name="Merck">{{cite web|url=http://www.merckmanuals.com/vet/toxicology/toxicities_from_human_drugs/analgesics_toxicity.html|title=Analgesics (toxicity) |publisher=Merck|archive-url= https://web.archive.org/web/20150411095033/http://www.merckmanuals.com/vet/toxicology/toxicities_from_human_drugs/analgesics_toxicity.html |archive-date=11 April 2015 |url-status=live|access-date=19 January 2018}}</ref> but the recommended dose for relief of pain and fever and for treating [[thrombophilia|blood clotting diseases]] in cats is 10{{nbsp}}mg/kg every 48 hours to allow for metabolization.<ref name="Edwards-2016" /><ref>{{cite web|url=http://www.ansci.cornell.edu/plants/toxcat/toxcat.html|title=Plants poisonous to livestock|publisher=Cornell University Department of Animal Science|archive-url=https://web.archive.org/web/20150816192109/http://www.ansci.cornell.edu/plants/toxcat/toxcat.html|archive-date=16 August 2015|url-status=live|access-date=3 March 2016}}</ref>
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* {{cite journal | vauthors = McTavish JR | title = What's in a name? Aspirin and the American Medical Association | journal = Bulletin of the History of Medicine | volume = 61 | issue = 3 | pages = 343–66 | date = 1987 | pmid = 3311247 | doi = | jstor = 44442097 }}
* {{cite encyclopedia |vauthors=Ling G |title=Aspirin |url=http://www.madehow.com/Volume-1/Aspirin.html |encyclopedia=How Products Are Made |volume=1 |publisher=Thomson Gale |year=2005}}
*{{cite book|title= Aspirin: the Remarkable Story of a Wonder Drug |author= Diarmuid Jeffreys |publisher=Bloomsbury |date=2004 }}
{{refend}}
== External links ==
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