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Benzbromarone

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Benzbromarone
Benzbromarone.svg
Clinical data
AHFS/Drugs.com International Drug Names
ATC code
Identifiers
  • (3,5-dibromo-4-hydroxyphenyl)-(2-ethyl-1-benzofuran-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.020.573
Chemical and physical data
Formula C17H12Br2O3
Molar mass 424.088 g·mol−1
3D model (JSmol)
Melting point 161 to 163 °C (322 to 325 °F)
  • Brc1cc(cc(Br)c1O)C(=O)c2c3ccccc3oc2CC
  • 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 checkY
  • Key:WHQCHUCQKNIQEC-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Benzbromarone 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.

Mechanism of action

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.

History

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In 2003, the drug was withdrawn by Sanofi-Synthélabo, after reports of serious hepatotoxicity, although it is still marketed in several countries by other drug companies.


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