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WEKX/sandbox
Clinical data
Pronunciationacetylsalicylic acid /əˌsiːtəlˌsæl[invalid input: 'ɨ']ˈsɪl[invalid input: 'ɨ']k/
Other names2-acetoxybenzoic acid
acetylsalicylate
acetylsalicylic acid
O-acetylsalicylic acid
AHFS/Drugs.comMonograph
MedlinePlusa682878
License data
Pregnancy
category
  • AU: C
Routes of
administration		Most commonly oral, also rectal, lysine acetylsalicylate may be given intravenously or intramuscularly
ATC code
Legal status
Legal status
  • AU: S2 (Pharmacy medicine) except when given intravenously (in which case it is schedule 4), used in animal medicine (schedule 5/6) or when the dose is higher than usual.
  • UK: General sales list (GSL, OTC)
  • US: OTC
Pharmacokinetic data
Bioavailability80–100%[1]
Protein binding80–90%[2]
MetabolismHepatic, (CYP2C19 and possibly CYP3A), some is also hydrolysed to salicylate in the gut wall.[2]
Elimination half-lifeDose-dependent; 2–3 hours for low doses, 15–30 hours for large doses.[2]
ExcretionUrine (80–100%), sweat, saliva, feces[1]
Identifiers
  • 2-(acetyloxy)benzoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
Chemical and physical data
FormulaC9H8O4
Molar mass180.157 g/mol g·mol−1
3D model (JSmol)
Density1.40 g/cm3
Melting point135 °C (275 °F)
Boiling point140 °C (284 °F) (decomposes)
Solubility in water3 mg/mL (20 °C)
  • O=C(Oc1ccccc1C(=O)O)C
  • 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 medication, often used to treat pain, fever, and inflammation.[2] Aspirin is also used long-term, at low doses, to help prevent heart attacks, strokes, and blood clot formation in people at high risk of developing blood clots.[3] Low doses of aspirin may be given immediately after a heart attack to prevent clotting and reduce the risk of another heart attack or the death of heart tissue.[4][5] Aspirin may be effective at preventing certain types of cancer, particularly colorectal cancer.[6][7][8]

The main side effects of aspirin are gastric ulcers, stomach bleeding[3], and ringing in the ears, especially with higher doses. While daily aspirin can help prevent a clot-related stroke, it may increase risk of a bleeding stroke (hemorrhagic stroke).[9] In children and adolescents, aspirin is not recommended for flu-like symptoms or viral illnesses, because of the risk of Reye's syndrome.[10]

Medical use

[edit]

Aspirin is used in the treatment of a number of conditions, including fever, pain, rheumatic fever, and inflammatory diseases, such as rheumatoid arthritis, pericarditis, and Kawasaki disease.[11] Lower doses of aspirin have also shown to reduce the risk of death from a heart attack, or the risk of stroke in some circumstances.[12][13][14] There is some evidence that aspirin is effective at preventing colorectal cancer, though the mechanisms of this effect are unclear.[15] In the United States low dose aspirin is deemed reasonable in those between 50 and 70 years old who have a more than 10% risk of cardiovascular disease and are not at an increased risk of bleeding who are otherwise healthy.[16]

WEKX/sandbox
Clinical data
AHFS/Drugs.comInternational Drug Names
License data
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
Pharmacokinetic data
BioavailabilityNot applicable (IV only)
Protein binding94 to 98%
MetabolismHepatic (mostly CYP3A4-mediated)
Elimination half-life180 hours (mean)
ExcretionMostly fecal
Identifiers
  • (1'R,6R,6aR,7R,13S,14S,16R)-6',8,14-trihydroxy-7',9-dimethoxy-4,10,23-trimethyl-19-oxo-3',4',6,7,12,13,14,16-octahydrospiro[6,16-(epithiopropano-oxymethano)-7,13-imino-6aH-1,3-dioxolo[7,8]isoquino[3,2-b][3]benzazocine-20,1'(2'H)-isoquinolin]-5-yl acetate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC39H43N3O11S
Molar mass761.84 g/mol g·mol−1
3D model (JSmol)
  • Cc1cc2c(c(c1OC)O)[C@@H]3[C@@H]4[C@H]5c6c(c7c(c(c6OC(=O)C)C)OCO7)[C@@H](N4[C@H]([C@H](C2)N3C)O)COC(=O)[C@@]8(CS5)c9cc(c(cc9CCN8)O)OC
  • InChI=1S/C39H43N3O11S/c1-16-9-20-10-22-37(46)42-23-13-50-38(47)39(21-12-25(48-5)24(44)11-19(21)7-8-40-39)14-54-36(30(42)29(41(22)4)26(20)31(45)32(16)49-6)28-27(23)35-34(51-15-52-35)17(2)33(28)53-18(3)43/h9,11-12,22-23,29-30,36-37,40,44-46H,7-8,10,13-15H2,1-6H3/t22-,23-,29+,30+,36+,37-,39+/m0/s1
  • Key:PKVRCIRHQMSYJX-AIFWHQITSA-N
 ☒NcheckY (what is this?)  (verify)
superdrug
Clinical data
License data
  1. ^ a b "Zorprin, Bayer Buffered Aspirin (aspirin) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 3 April 2014.
  2. ^ a b c d Brayfield, A, ed. (14 January 2014). "Aspirin". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 3 April 2014.
  3. ^ a b Lewis, HD; Davis, JW; Archibald, DG; Steinke, WE; Smitherman, TC; Doherty Je, JE; Schnaper, HW; Lewinter, MM; Linares, E; Pouget, JM; Sabharwal, SC; Chesler, E; Demots, H (1983). "Protective Effects of Aspirin against Acute Myocardial Infarction and Death in Men with Unstable Angina". New England Journal of Medicine. 309 (7): 396–403. doi:10.1056/NEJM198308183090703. PMID 6135989.
  4. ^ Julian, D G; D A Chamberlain; S J Pocock (24 September 1996). "A comparison of aspirin and anticoagulation following thrombolysis for myocardial infarction (the AFTER study): a multicentre unblinded randomised clinical trial". BMJ. 313 (7070). British Medical Journal: 1429–1431. doi:10.1136/bmj.313.7070.1429. PMC 2353012. PMID 8973228.
  5. ^ Krumholz, HM; Radford, MJ; Ellerbeck, EF; Hennen, J; Meehan, TP; Petrillo, M; Wang, Y; Kresowik, TF; Jencks, SF (1995). "Aspirin in the treatment of acute myocardial infarction in elderly Medicare beneficiaries. Patterns of use and outcomes". Circulation. 92 (10): 2841–2847. doi:10.1161/01.CIR.92.10.2841. PMID 7586250.
  6. ^ Algra, Annemijn M; Rothwell, Peter M (2012). "Effects of regular aspirin on long-term cancer incidence and metastasis: A systematic comparison of evidence from observational studies versus randomised trials". The Lancet Oncology. 13 (5): 518–27. doi:10.1016/S1470-2045(12)70112-2. PMID 22440112.
  7. ^ Rothwell, Peter M; Price, Jacqueline F; Fowkes, F Gerald R; Zanchetti, Alberto; Roncaglioni, Maria Carla; Tognoni, Gianni; Lee, Robert; Belch, Jill FF; Wilson, Michelle; Mehta, Ziyah; Meade, Tom W (2012). "Short-term effects of daily aspirin on cancer incidence, mortality, and non-vascular death: Analysis of the time course of risks and benefits in 51 randomised controlled trials". The Lancet. 379 (9826): 1602–1612. doi:10.1016/S0140-6736(11)61720-0. PMID 22440946. S2CID 205964516. {{cite journal}}: Unknown parameter |displayauthors= ignored (|display-authors= suggested) (help)
  8. ^ Rothwell, Peter M; Wilson, Michelle; Price, Jacqueline F; Belch, Jill FF; Meade, Tom W; Mehta, Ziyah (2012). "Effect of daily aspirin on risk of cancer metastasis: A study of incident cancers during randomised controlled trials". The Lancet. 379 (9826): 1591–1601. doi:10.1016/S0140-6736(12)60209-8. PMID 22440947. S2CID 13943035.
  9. ^ "Daily aspirin therapy: Understand the benefits and risks". MayoClinic.org. Mayo Clinic. Retrieved 21 March 2015.
  10. ^ Macdonald S (2002). "Aspirin use to be banned in under 16-year olds". BMJ. 325 (7371): 988c–988. doi:10.1136/bmj.325.7371.988/c. PMC 1169585. PMID 12411346.
  11. ^ "Aspirin". The American Society of Health-System Pharmacists. Retrieved 3 April 2011.
  12. ^ "Aspirin for reducing your risk of heart attack and stroke: know the facts". U.S. Food and Drug Administration. Retrieved 26 July 2012.
  13. ^ "Aspirin for the prevention of cardiovascular disease". U.S. Preventive Services Task Force. Retrieved 26 July 2012.
  14. ^ Seshasai, SR; Wijesuriya, S; Sivakumaran, R; Nethercott, S; Erqou, S; Sattar, N; Ray, KK (13 February 2012). "Effect of aspirin on vascular and nonvascular outcomes: meta-analysis of randomized controlled trials". Archives of Internal Medicine. 172 (3): 209–16. doi:10.1001/archinternmed.2011.628. PMID 22231610.
  15. ^ Algra, AM; Rothwell, PM (May 2012). "Effects of regular aspirin on long-term cancer incidence and metastasis: a systematic comparison of evidence from observational studies versus randomised trials". The Lancet Oncology. 13 (5): 518–27. doi:10.1016/S1470-2045(12)70112-2. PMID 22440112.
  16. ^ Bibbins-Domingo, K; U.S. Preventive Services Task, Force (21 June 2016). "Aspirin use for the primary prevention of cardiovascular disease and colorectal cancer: U.S. Preventive Services Task Force recommendation statement". Annals of Internal Medicine. 164 (12): 836–45. doi:10.7326/M16-0577. PMID 27064677.
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