Advil

Ibuprofen

Clinical data
Pronunciation	/ˈaɪbjuːproʊfɛn/, /aɪbjuːˈproʊfən/, EYE-bew-PROH-fən
Trade names	Advil, Motrin, Nurofen, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682159
License data	US FDA: Ibuprofen
Pregnancy category	AU: C US: C (Risk not ruled out) D (US) at ≥30 weeks of gestation, due to the potential for premature closure of the ductus arteriosus
Routes of administration	by mouth, rectal, topical, and intravenous
ATC code	C01EB16 (WHO) G02CC01 (WHO) M01AE01 (WHO) M02AA13 (WHO) R02AX02 (WHO)
Legal status
Legal status	AU: S2 (Pharmacy only) to Prescription Only (S4) CA: OTC UK: General sales list (GSL, OTC) US: OTC / Rx-only
Pharmacokinetic data
Bioavailability	87–100% (oral), 87% (rectal)
Protein binding	98%
Metabolism	Hepatic (CYP2C9)
Onset of action	30 min
Biological half-life	1.3–3 h
Excretion	Urine (95%)
Identifiers
IUPAC name (RS)-2-(4-(2-Methylpropyl)phenyl)propanoic acid
Synonyms	isobutylphenylpropionic acid
CAS Number	15687-27-1 Y
PubChem CID	3672
IUPHAR/BPS	2713
DrugBank	DB01050 Y
ChemSpider	3544 Y
UNII	WK2XYI10QM
KEGG	D00126 Y
ChEBI	CHEBI:5855 Y
ChEMBL	CHEMBL521 Y
PDB ligand	IBP (PDBe, RCSB PDB)
ECHA InfoCard	100.036.152
Chemical and physical data
Formula	C13H18O2
Molar mass	206.29 g/mol
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
Density	1.03 g/ml g/cm3
Melting point	75 to 78 °C (167 to 172 °F)
Boiling point	157 °C (315 °F)
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) Y Key:HEFNNWSXXWATRW-UHFFFAOYSA-N Y

Ibuprofen is a medication in the nonsteroidal anti-inflammatory drug (NSAID) class that is used for treating pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. About 60% of people improve with any given NSAID, and it is recommended that if one does not work then another should be tried. It may also be used to close a patent ductus arteriosus in a premature baby. It can be used 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 fewer 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 myocardial infarction; however, at higher doses it may. Ibuprofen can also result in worsened asthma. While it is unclear if it is safe in early pregnancy, it appears to be harmful in later pregnancy and therefore is not recommended. Like other NSAIDs, it works by inhibiting the making of prostaglandins by decreasing the activity of the enzyme cyclooxygenase. Ibuprofen might be a weaker anti-inflammatory than other NSAIDs.

Ibuprofen was discovered in 1961 by Stewart Adams and marketed as Brufen. It is available under a number of trade names, including Advil and Motrin. It was first marketed in 1969 in the United Kingdom and in the United States in 1974. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world is between 0.01 and 0.04 USD per dose. In the United States it costs about 0.05 USD per dose.