Acetylsalicylic acid

Aspirin
INN: acetylsalicylic acid
Clinical data


Pronunciation	acetylsalicylic acid /əˌsiːtəlˌsælᵻˈsɪlᵻk/
AHFS/Drugs.com	Monograph
MedlinePlus	a682878
License data	US FDA: Aspirin
Pregnancy category	AU: C US: C (Risk not ruled out) D in the 3rd trimester
Routes of administration	by mouth, rectal, lysine acetylsalicylate may be given intravenously or intramuscularly
ATC code	A01AD05 (WHO) B01AC06 (WHO), N02BA01 (WHO)
Legal status
Legal status	AU: S2 (Pharmacy only) 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
Bioavailability	80–100%
Protein binding	80–90%
Metabolism	Liver, (CYP2C19 and possibly CYP3A), some is also hydrolysed to salicylate in the gut wall.
Biological half-life	Dose-dependent; 2 h to 3 h for low doses, 15 h to 30 h for large doses.
Excretion	Urine (80–100%), sweat, saliva, feces
Identifiers
IUPAC name 2-(acetyloxy)benzoic acid
Synonyms	2-acetoxybenzoic acid acetylsalicylate acetylsalicylic acid O-acetylsalicylic acid
CAS Number	50-78-2^Y
PubChem CID	2244
IUPHAR/BPS	4139
DrugBank	DB00945^Y
ChemSpider	2157^Y
UNII	R16CO5Y76E
KEGG	D00109^Y
ChEBI	CHEBI:15365^Y
ChEMBL	CHEMBL25^Y
PDB ligand	AIN (PDBe, RCSB PDB)
ECHA InfoCard	100.000.059
Chemical and physical data
Formula	C₉H₈O₄
Molar mass	180.157 g/mol
3D model (Jmol)	Interactive image
Density	1.40 g/cm³
Melting point	135 °C (275 °F)
Boiling point	140 °C (284 °F) (decomposes)
Solubility in water	3 mg/mL (20 °C)
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)^Y Key:BSYNRYMUTXBXSQ-UHFFFAOYSA-N^Y

Aspirin, also known as acetylsalicylic acid (ASA), is a medication used to treat pain, fever, and inflammation. Specific inflammatory conditions in which it is used include Kawasaki disease, pericarditis, and rheumatic fever. Aspirin given shortly after a heart attack decreases the risk of death. Aspirin is also used long-term to help prevent heart attacks, strokes, and blood clots, in people at high risk. Aspirin may also decrease the risk of certain types of cancer, particularly colorectal cancer. For pain or fever, effects typically begin within 30 minutes. Aspirin is a nonsteroidal anti-inflammatory drug (NSAID) and works similar to other NSAIDs but it is also an antiplatelet and suppresses the normal functioning of platelets.

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

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