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Aspirin information


Acetylsalicylic acid
Clinical data
Pronunciation/əˌstəlˌsælɪˈsɪlɪk/
Trade namesBayer Aspirin, others
Other names
  • 2-acetoxybenzoic acid
  • o-acetylsalicylic acid
  • acetylsalicylic acid
  • acetyl salicylate
  • monoacetic acid ester of salicylic acid[1]
AHFS/Drugs.comMonograph
MedlinePlusa682878
License data
  • US DailyMed: Acetylsalicylic acid
Pregnancy
category
  • AU: C[2]
Routes of
administration
Oral, rectal
Drug classNonsteroidal anti-inflammatory drug (NSAID)
ATC code
  • A01AD05 (WHO) B01AC06 (WHO), N02BA01 (WHO)
Legal status
Legal status
  • AU: OTC / Schedule 2, 4, 5, 6[3][4]
  • CA: OTC[5]
  • UK: General sales list (GSL, OTC)
  • US: OTC / Rx-only
Pharmacokinetic data
Bioavailability80–100%[6]
Protein binding80–90%[7]
MetabolismLiver (CYP2C19 and possibly CYP3A), some is also hydrolysed to salicylate in the gut wall.[7]
Elimination half-lifeDose-dependent; 2–3 h for low doses (100 mg or less), 15–30 h for larger doses.[7]
ExcretionUrine (80–100%), sweat, saliva, feces[6]
Identifiers
IUPAC name
  • 2-acetyloxybenzoic acid[8]
CAS Number
  • 50-78-2 checkY
PubChem CID
  • 2244
IUPHAR/BPS
  • 4139
DrugBank
  • DB00945 checkY
ChemSpider
  • 2157 checkY
UNII
  • R16CO5Y76E
KEGG
  • D00109 checkY
  • C01405 checkY
ChEBI
  • CHEBI:15365 checkY
ChEMBL
  • ChEMBL25 checkY
PDB ligand
  • AIN (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID5020108 Edit this at Wikidata
ECHA InfoCard100.000.059 Edit this at Wikidata
Chemical and physical data
FormulaC9H8O4
Molar mass180.159 g·mol−1
3D model (JSmol)
  • Interactive image
Density1.40 g/cm3
Melting point135 °C (275 °F) [9]
Boiling point140 °C (284 °F) (decomposes)
Solubility in water3 g/L
SMILES
  • O=C(C)Oc1ccccc1C(=O)O
InChI
  • InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12) checkY
  • Key:BSYNRYMUTXBXSQ-UHFFFAOYSA-N checkY
  (verify)

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.[10] Specific inflammatory conditions which aspirin is used to treat include Kawasaki disease, pericarditis, and rheumatic fever.[10]

Aspirin is also used long-term to help prevent further heart attacks, ischaemic strokes, and blood clots in people at high risk.[10] For pain or fever, effects typically begin within 30 minutes.[10] Aspirin works similarly to other NSAIDs but also suppresses the normal functioning of platelets.[10]

One common adverse effect is an upset stomach.[10] More significant side effects include stomach ulcers, stomach bleeding, and worsening asthma.[10] Bleeding risk is greater among those who are older, drink alcohol, take other NSAIDs, or are on other blood thinners.[10] Aspirin is not recommended in the last part of pregnancy.[10] It is not generally recommended in children with infections because of the risk of Reye syndrome.[10] High doses may result in ringing in the ears.[10]

A 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.[11][12] In 1853, chemist Charles Frédéric Gerhardt treated the medicine sodium salicylate with acetyl chloride to produce acetylsalicylic acid for the first time.[13] Over the next 50 years, other chemists, mostly of the German company Bayer, established the chemical structure and devised more efficient production methods.[13]: 69–75 

Aspirin is available without medical prescription as a proprietary or generic medication[10] in most jurisdictions. It is one of the most widely used medications globally, with an estimated 40,000 tonnes (44,000 tons) (50 to 120 billion pills)[clarification needed] consumed each year,[11][14] and is on the World Health Organization's List of Essential Medicines.[15] In 2021, it was the 34th most commonly prescribed medication in the United States, with more than 17 million prescriptions.[16][17]

  1. ^ McTavish J (Fall 1987). "What's in a Name? Aspirin and the American Medical Association". Bulletin of the History of Medicine. 61 (3).
  2. ^ "Aspirin Use During Pregnancy". Drugs.com. 2 April 2018. Retrieved 29 December 2019.
  3. ^ "OTC medicine monograph: Aspirin tablets for oral use". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 4 April 2023.
  4. ^ "Poisons Standard October 2022". Australian Government Federal Register of Legislation. 26 September 2022. Retrieved 9 January 2023.
  5. ^ "Aspirin Product information". Health Canada. 22 October 2009. Retrieved 20 August 2023.
  6. ^ a b "Zorprin, Bayer Buffered Aspirin (aspirin) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 7 April 2014. Retrieved 3 April 2014.
  7. ^ a b c Brayfield A, ed. (14 January 2014). "Aspirin". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 3 April 2014.
  8. ^ CID 2244 from PubChem
  9. ^ Cite error: The named reference b92 was invoked but never defined (see the help page).
  10. ^ a b c d e f g h i j k l "Aspirin". American Society of Health-System Pharmacists. 29 November 2021. Archived from the original on 25 April 2017 – via Drugs.com.
  11. ^ a b Jones A (2015). Chemistry: An Introduction for Medical and Health Sciences. John Wiley & Sons. pp. 5–6. ISBN 978-0-470-09290-3.
  12. ^ Ravina E (2011). The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. p. 24. ISBN 978-3-527-32669-3.
  13. ^ a b Jeffreys D (2008). Aspirin the remarkable story of a wonder drug. Bloomsbury Publishing USA. ISBN 978-1-59691-816-0. Archived from the original on 8 September 2017.: 46–48 
  14. ^ Warner TD, Mitchell JA (October 2002). "Cyclooxygenase-3 (COX-3): filling in the gaps toward a COX continuum?". Proceedings of the National Academy of Sciences of the United States of America. 99 (21): 13371–3. Bibcode:2002PNAS...9913371W. doi:10.1073/pnas.222543099. PMC 129677. PMID 12374850.
  15. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  16. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  17. ^ "Aspirin - Drug Usage Statistics, US 2013-2021". ClinCalc. Retrieved 14 January 2024.

and 22 Related for: Aspirin information

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Aspirin

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Aspirin, also known as acetylsalicylic acid (ASA), is a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and/or inflammation, and...

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Reye syndrome

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syndrome. Prevention is typically by avoiding the use of aspirin in children. When aspirin was withdrawn for use in children in the US and UK in the...

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History of aspirin

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Aspirin (acetylsalicylic acid), an organic compound that does not occur in nature, was first synthesised in 1899. In 1897, scientists at the drug and...

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Ibuprofen

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after IR aspirin, and 8 hours or more for ibuprofen taken before IR aspirin. However, this timing cannot be recommended for enteric-coated aspirin. If ibuprofen...

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Mechanism of action of aspirin

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Aspirin causes several different effects in the body, mainly the reduction of inflammation, analgesia (relief of pain), the prevention of clotting, and...

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Salicylic acid

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solid, it is a precursor to and a metabolite of acetylsalicylic acid (aspirin). It is a plant hormone, and has been listed by the EPA Toxic Substances...

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Bayer

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launched the compound acetylsalicylic acid under the trademarked name Aspirin. Aspirin is on the World Health Organization's List of Essential Medicines....

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Robert Asprin

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Robert Lynn Asprin (June 28, 1946 – May 22, 2008) was an American science fiction and fantasy author and active fan, known best for his humorous series...

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Willow

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an analgesic effect. This acid was named "Aspirin" by Hoffmann's employer Bayer AG. The discovery of aspirin is therefore only indirectly connected to...

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Felix Hoffmann

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the Bayer trade name of "heroin". He is also credited with synthesizing aspirin, though whether he did this under his own initiative or under the instruction...

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PubMed

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"attack"[All Fields]) OR "heart attack"[All Fields]) AND ("aspirin"[MeSH Terms] OR "aspirin"[All Fields]) AND ("prevention and control"[Subheading] OR...

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Stroke

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problematic carotid narrowing, and warfarin in people with atrial fibrillation. Aspirin or statins may be recommended by physicians for prevention. Stroke is a...

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Salicylate poisoning

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Salicylate poisoning, also known as aspirin poisoning, is the acute or chronic poisoning with a salicylate such as aspirin. The classic symptoms are ringing...

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Lysine acetylsalicylate

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acetylsalicylate, also known as aspirin DL-lysine or lysine aspirin, is a more soluble form of acetylsalicylic acid (aspirin). As with aspirin itself, it is a nonsteroidal...

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Clopidogrel

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disease and stroke in those at high risk. It is also used together with aspirin in heart attacks and following the placement of a coronary artery stent...

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High anion gap metabolic acidosis

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More rarely, it may be caused by ingesting methanol or overdosing on aspirin. The delta ratio is a formula that can be used to assess elevated anion...

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Antiplatelet drug

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treatment of both stable and unstable ischemic heart disease. Most commonly, aspirin is used as a single medication in cases of uncomplicated stable angina...

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Salicylamide

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Its medicinal uses are similar to those of aspirin. Salicylamide is used in combination with both aspirin and caffeine in the over-the-counter pain remedy...

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Coronary artery disease

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as prevention. Additional medications such as antiplatelets (including aspirin), beta blockers, or nitroglycerin may be recommended. Procedures such as...

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Myocardial infarction

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and less often creatine kinase MB. Treatment of an MI is time-critical. Aspirin is an appropriate immediate treatment for a suspected MI. Nitroglycerin...

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Nasal polyp

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occur more commonly among people who have allergies, cystic fibrosis, aspirin sensitivity, or certain infections. The polyp itself represents an overgrowth...

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Mechanism of action

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which the mechanism of action is known. One example is aspirin. The mechanism of action of aspirin involves irreversible inhibition of the enzyme cyclooxygenase;...

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