Structure via PubChem · Public domain (PubChem)
benzbromarone
Sign in to saveAlso known as 2-ethyl-3-(3,5-dibrom-4-hydroxybenzoyl)benzofuran, 3,5-dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl ketone, Uroleap (TN)
Benzbromarone is a uricosuric agent and weak non-competitive inhibitor of xanthine oxidase used in the treatment of gout. It is a brominated analogue of withdrawn uricosuric benziodarone and benzarone, and is structurally related to the antiarrhythmic amiodarone.
Chemical data
- Formula
- C17H12Br2O3
- Molecular weight
- 424.1 g/mol
- IUPAC name
- (3,5-dibromo-4-hydroxyphenyl)-(2-ethyl-1-benzofuran-3-yl)methanone
- SMILES
- CCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)Br)O)Br
- InChIKey
- WHQCHUCQKNIQEC-UHFFFAOYSA-N
- XLogP
- 5.7
- Polar surface area
- 50.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Admin. routes
- oral
- Indications
- gout, hyperuricemia, idiopathic pulmonary arterial hypertension
via ChEMBL · EBI
Research
836 papers- Benzbromarone in the treatment of gout.Advances in rheumatology (London, England) · 2019
- Slow Metabolism-Driven Amplification of Hepatic PPARγ Agonism Mediates Benzbromarone-Induced Obesity-Specific Liver Injury.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025
- Benzbromarone interferes with the interaction between Hsp90 and Aha1 by interacting with both of them.Communications biology · 2025
- A benefit-risk assessment of benzbromarone in the treatment of gout. Was its withdrawal from the market in the best interest of patients?Drug safety · 2008
- [Benzbromarone in the treatment of gout].Reumatologia · 1980
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 421.915318444
Show 4 more facts
- chemical formula
- C₁₇H₁₂Br₂O₃
- canonical SMILES
- CCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)Br)O)Br
- Commons category
- Benzbromarone
- subject has role
- xanthine oxidase inhibitor
via Wikidata · CC0
~5 min read
Encyclopedic overview
8 sectionsContents
- Medical uses
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Side effects
- Drug interactions
- History
- References
Benzbromarone is a uricosuric agent and weak non-competitive inhibitor of xanthine oxidase used in the treatment of gout. It is a brominated analogue of withdrawn uricosuric benziodarone and benzarone, and is structurally related to the antiarrhythmic amiodarone.
Benzbromarone was withdrawn from most European countries in 2003 due to the risk of idiosyncratic hepatotoxicity, but remains heavily used in Asia and South America. Despite this risk, it is generally considered highly effective and well tolerated in most patients. Clinical trials dating back to 1981 and as recent as 2022, as well as meta-analyses, have reported its superior efficacy compared to both non-uricosuric xanthine oxidase inhibitors (allopurinol and febuxostat) and another uricosuric drug, probenecid.
Excerpted from Wikipedia’s “benzbromarone” article, available under the CC BY-SA 4.0 licence.