Benzbromarone

Benzbromarone

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	M04AB03 (WHO)
Identifiers
IUPAC name (3,5-dibromo-4-hydroxyphenyl)-(2-ethyl-1-benzofuran-3-yl)methanone
CAS Number	3562-84-3 N
PubChem CID	2333
ChemSpider	2243 Y
UNII	4POG0RL69O
ChEBI	CHEBI:3023 Y
ChEMBL	CHEMBL388590 Y
ECHA InfoCard	100.020.573
Chemical and physical data
Formula	C17H12Br2O3
Molar mass	424.083 g/mol
3D model (Jmol)	Interactive image
Melting point	161 to 163 °C (322 to 325 °F)
SMILES Brc1cc(cc(Br)c1O)C(=O)c2c3ccccc3oc2CC
InChI InChI=1S/C17H12Br2O3/c1-2-13-15(10-5-3-4-6-14(10)22-13)16(20)9-7-11(18)17(21)12(19)8-9/h3-8,21H,2H2,1H3 Y Key:WHQCHUCQKNIQEC-UHFFFAOYSA-N Y
NY (what is this?)

Benzbromarone (INN) is a uricosuric agent and non-competitive inhibitor of xanthine oxidase used in the treatment of gout, especially when allopurinol, a first-line treatment, fails or produces intolerable adverse effects. It is structurally related to the antiarrhythmic amiodarone.

Benzbromarone is highly effective and well tolerated, and clinical trials as early as 1981 and as recently as April 2008 have suggested it is superior to both allopurinol, a non-uricosuric xanthine oxidase inhibitor, and probenecid, another uricosuric drug.

Benzbromarone is a very potent inhibitor of CYP2C9. Several analogues of the drug have been developed as CYP2C9 and CYP2C19 inhibitors for use in research.

Benzbromarone was introduced in the 1970s and was viewed as having few associated serious adverse reactions. It was registered in about 20 countries throughout Europe, Asia and South America.

In 2003, the drug was withdrawn by Sanofi-Synthélabo, after reports of serious hepatotoxicity, although it is still marketed in several countries by other drug companies.