Benzbromarone

Title: Benzbromarone
CAS Registry Number: 3562-84-3
CAS Name: (3,5-Dibromo-4-hydroxyphenyl)(2-ethyl-3-benzofuranyl)methanone
Additional Names: 3,5-dibromo-4-hydroxyphenyl 2-ethyl-3-benzofuranyl ketone; 3-(3,5-dibromo-4-hydroxybenzoyl)-2-ethylbenzofuran; 2-ethyl-3-benzofuranyl 4-hydroxy-3,5-dibromophenyl ketone; 2-ethyl-3-(3,5-dibromo-4-hydroxybenzoyl)benzofuran; 2-ethyl-3-(3,5-dibromo-4-hydroxybenzoyl)oxaindene; 2-ethyl-3-benzofuryl 3,5-dibromo-4-hydroxyphenyl ketone
Manufacturers' Codes: L-2214; MJ-10061
Trademarks: Azubromaron (Azupharma); Desuric (Sanofi Winthrop); Max-Uric (Labinca); Minuric (R & C); Narcaricin (Heumann); Normurat (Grenthal); Uricovac (Sanofi Winthrop); Urinorm (Torii)
Molecular Formula: C17H12Br2O3
Molecular Weight: 424.08
Percent Composition: C 48.15%, H 2.85%, Br 37.68%, O 11.32%
Literature References: Prepn: BE 553621 (1957 to Labaz); Buu-Hoi et al., J. Chem. Soc. 1957, 625; Buu-Hoi, Beaudet, US 3012042 (1961 to Soc. Belge l'Azote Prod. Chim. Marly). Structure-activity study: Delbarre et al., Chim. Ther. 3, 470 (1968). Pharmacology of hypouricemic effect: D. S. Sinclair, I. H. Fox, J. Rheumatol. 2, 437 (1975). Pharmacokinetic and clinical studies: T. F. Yu, ibid. 3, 305 (1976). Pharmacokinetics and biotransformation in man: H. Ferber et al., Eur. J. Clin. Pharmacol. 19, 431 (1981). HPLC determn in serum: H. Vergin et al., J. Chromatogr. 183, 383 (1980).
Properties: Yellowish prisms, mp 151°.
Melting point: mp 151°
Therap-Cat: Uricosuric.
Keywords: Uricosuric.
Benzenearsonic Acid Benzeneboronic Acid Benzenestibonic Acid Benzenesulfonic Acid Benzenesulfonic Anhydride

Benzbromarone
Benzbromarone V.1.svg
Systematic (IUPAC) name
(3,5-dibromo-4-hydroxyphenyl)- (2-ethyl-3-benzofuranyl)methanone
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 3562-84-3 N
ATC code M04AB03
PubChem CID 2333
ChemSpider 2243 YesY
UNII 4POG0RL69O YesY
ChEBI CHEBI:3023 YesY
ChEMBL CHEMBL388590 YesY
Chemical data
Formula C17H12Br2O3 
Mol. mass 424.083 g/mol
Physical data
Melt. point 161–163 °C (322–325 °F)
 N (what is this?)  (verify)

Benzbromarone (INN) is a uricosuric agent and non-competitive inhibitor of xanthine oxidase[1] 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.[2]

Benzbromarone is highly effective and well tolerated,[3][4][5][6] and clinical trials as early as 1981 and as recently as April 2008 have suggested it is superior to both allopurinol, a xanthine oxidase inhibitor but not uricouric, and probenecid, another uricouric drug.[7][8]