Ibuprofen

Ibuprofen
Clinical data
Pronunciation	/ˈaɪbjuːproʊfɛn/, /aɪbjuːˈproʊfən/, EYE-bew-PROH-fən
Trade names	Advil, Motrin, Nurofen, others
Other names	isobutylphenylpropionic acid
AHFS/Drugs.com	Monograph
MedlinePlus	a682159
License data	US DailyMed: Ibuprofen;
Pregnancy; category	AU: C;
Routes of; administration	Oral (by mouth), rectal, topical, intravenous
ATC code	C01EB16 (WHO) G02CC01 (WHO) M01AE01 (WHO) M02AA13 (WHO) R02AX02 (WHO);
Legal status
Legal status	AU: OTC; CA: OTC; UK: General sales list (GSL, OTC); US: WARNINGOTC / Rx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	80–100% (orally), 87% (rectal)
Protein binding	98%
Metabolism	Liver (CYP2C9)
Metabolites	ibuprofen glucuronide, 2-hydroxyibuprofen, 3-hydroxyibuprofen, carboxy-ibuprofen, 1-hydroxyibuprofen
Onset of action	30 min
Elimination half-life	2–4 h
Excretion	Urine (95%)
Identifiers
	IUPAC name (RS)-2-(4-(2-Methylpropyl)phenyl)propanoic acid;
CAS Number	15687-27-1 ;
PubChem CID	3672;
IUPHAR/BPS	2713;
DrugBank	DB01050 ;
ChemSpider	3544 ;
UNII	WK2XYI10QM;
KEGG	D00126 ;
ChEBI	CHEBI:5855 ;
ChEMBL	ChEMBL521 ;
PDB ligand	IBP (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID5020732 ;
ECHA InfoCard	100.036.152
Chemical and physical data
Formula	C13H18O2
Molar mass	206.285 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
Density	1.03 g/cm3
Melting point	75 to 78 °C (167 to 172 °F)
Boiling point	157 °C (315 °F) at 4 mmHg
Solubility in water	0.021 mg/mL (20 °C)
	SMILES CC(C)Cc1ccc(cc1)[C@@H](C)C(=O)O;
	InChI InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15) ; Key:HEFNNWSXXWATRW-UHFFFAOYSA-N ;
	(verify)

Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is used to relieve pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. It may also be used to close a patent ductus arteriosus in a premature baby. It can be used orally (by mouth) or intravenously. It typically begins working within an hour.

Common side effects include heartburn and a rash. Compared to other NSAIDs, it may have other side effects such as gastrointestinal bleeding. It increases the risk of heart failure, kidney failure, and liver failure. At low doses, it does not appear to increase the risk of heart attack; however, at higher doses it may. Ibuprofen can also worsen asthma. While its safety in early pregnancy is unclear, it appears to be harmful in later pregnancy, so it is not recommended during that period. Like other NSAIDs, it works by inhibiting the production of prostaglandins by decreasing the activity of the enzyme cyclooxygenase (COX). Ibuprofen is a weaker anti-inflammatory agent than other NSAIDs.

Ibuprofen was discovered in 1961 by Stewart Adams and John Nicholson while working at Boots UK Limited and initially marketed as Brufen. It is available under a number of brand names, including Nurofen, Advil, and Motrin. Ibuprofen was first marketed in 1969 in the United Kingdom and in 1974 in the United States. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2021, it was the 36th-most commonly prescribed medication in the United States, with more than 17 million prescriptions.

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