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'''Benzbromarone''' ([[International Nonproprietary Name|INN]]) is a [[uricosuric]] agent used in the treatment of [[gout]], especially when [[allopurinol]], a [[first-line treatment]], fails or produces intolerable [[adverse drug reaction|adverse effects]]. It is structurally related to the [[antiarrhythmic agent|antiarrhythmic]] [[amiodarone]].<ref name=Kumar>{{cite journal |author=Kumar V, Locuson CW, Sham YY, Tracy TS |title=Amiodarone analog-dependent effects on CYP2C9-mediated metabolism and kinetic profiles |journal=Drug Metab. Dispos. |volume=34 |issue=10 |pages=1688–96 |year=2006 |month=October |pmid=16815961 |doi=10.1124/dmd.106.010678 |url=}}</ref>
'''Benzbromarone''' ([[International Nonproprietary Name|INN]]) is a [[uricosuric]] agent used in the treatment of [[gout]], especially when [[allopurinol]], a [[first-line treatment]], fails or produces intolerable [[adverse drug reaction|adverse effects]]. It is structurally related to the [[antiarrhythmic agent|antiarrhythmic]] [[amiodarone]].<ref name=Kumar>{{cite journal |author=Kumar V, Locuson CW, Sham YY, Tracy TS |title=Amiodarone analog-dependent effects on CYP2C9-mediated metabolism and kinetic profiles |journal=Drug Metab. Dispos. |volume=34 |issue=10 |pages=1688–96 |year=2006 |month=October |pmid=16815961 |doi=10.1124/dmd.106.010678 |url=}}</ref>
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{{Antigout preparations}}
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[[Category:Antigout agents]]
[[Category:Antigout agents]]

Revision as of 22:51, 8 August 2012

Benzbromarone
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Clinical data
ATC code
Identifiers
CAS Number
PubChem CID
E number{{#property:P628}}
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Chemical and physical data
FormulaC17H12Br2O3
Molar mass424.083 g/mol
3D model (JSmol)
Melting point161 to 163 °C (Expression error: Unrecognized word "to". °F)

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Benzbromarone (INN) is a uricosuric agent 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.[1]

Benzbromarone is highly effective and well-tolerated,[2][3][4][5] and clinical trials as early as 1981 and as recently as April 2008 have suggested it is superior to both allopurinol and probenecid, another uricosuric drug.[6][7]

Effect on cytochrome P450

Benzbromarone is a very potent inhibitor of CYP2C9.[8][1] Several analogues of the drug have been developed as CYP2C9 and CYP2C19 inhibitors for use in research.[9][10]

Safety

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. [11]

See also

References

  1. ↑ 1.0 1.1 Kumar V, Locuson CW, Sham YY, Tracy TS (2006). "Amiodarone analog-dependent effects on CYP2C9-mediated metabolism and kinetic profiles". Drug Metab. Dispos. 34 (10): 1688–96. doi:10.1124/dmd.106.010678. PMID 16815961. Unknown parameter |month= ignored (help)
  2. ↑ Heel RC, Brogden RN, Speight TM, Avery GS (1977). "Benzbromarone: a review of its pharmacological properties and therapeutic use in gout and hyperuricaemia". Drugs. 14 (5): 349–66. PMID 338280. Unknown parameter |month= ignored (help)
  3. ↑ Masbernard A, Giudicelli CP (1981). "Ten years' experience with benzbromarone in the management of gout and hyperuricaemia". S. Afr. Med. J. 59 (20): 701–6. PMID 7221794. Unknown parameter |month= ignored (help)
  4. ↑ Perez-Ruiz F, Alonso-Ruiz A, Calabozo M, Herrero-Beites A, García-Erauskin G, Ruiz-Lucea E (1998). "Efficacy of allopurinol and benzbromarone for the control of hyperuricaemia. A pathogenic approach to the treatment of primary chronic gout". Ann. Rheum. Dis. 57 (9): 545–9. PMID 9849314. Unknown parameter |month= ignored (help)
  5. ↑ Reinders MK, van Roon EN, Houtman PM, Brouwers JR, Jansen TL (2007). "Biochemical effectiveness of allopurinol and allopurinol-probenecid in previously benzbromarone-treated gout patients". Clin. Rheumatol. 26 (9): 1459–65. doi:10.1007/s10067-006-0528-3. PMID 17308859. Unknown parameter |month= ignored (help)
  6. ↑ Schepers GW (1981). "Benzbromarone therapy in hyperuricaemia; comparison with allopurinol and probenecid". J. Int. Med. Res. 9 (6): 511–5. PMID 7033016.
  7. ↑ Reinders MK, van Roon EN, Jansen TL; et al. (2008). "Efficacy and tolerability of urate lowering drugs in gout: a randomised controlled trial of benzbromarone versus probenecid after failure of allopurinol". Ann. Rheum. Dis. doi:10.1136/ard.2007.083071. PMID 18250112. Unknown parameter |month= ignored (help)
  8. ↑ Hummel MA, Locuson CW, Gannett PM; et al. (2005). "CYP2C9 genotype-dependent effects on in vitro drug-drug interactions: switching of benzbromarone effect from inhibition to activation in the CYP2C9.3 variant". Mol. Pharmacol. 68 (3): 644–51. doi:10.1124/mol.105.013763. PMID 15955872. Unknown parameter |month= ignored (help)
  9. ↑ Locuson CW, Rock DA, Jones JP (2004). "Quantitative binding models for CYP2C9 based on benzbromarone analogues". Biochemistry. 43 (22): 6948–58. doi:10.1021/bi049651o. PMID 15170332. Unknown parameter |month= ignored (help)
  10. ↑ Locuson CW, Suzuki H, Rettie AE, Jones JP (2004). "Charge and substituent effects on affinity and metabolism of benzbromarone-based CYP2C19 inhibitors". J. Med. Chem. 47 (27): 6768–76. doi:10.1021/jm049605m. PMID 15615526. Unknown parameter |month= ignored (help)
  11. ↑ Lee MH, Graham GG, Williams KM, Day RO, A benefit-risk assessment of benzbromarone in the treatment of gout : was its withdrawal from the market in the best interest of patients? Drug Saf. 2008;31(8):643-65. PMID: 18636784

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