Benzbromarone

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Benzbromarone
Systematic (IUPAC) name
(3,5-dibromo-4-hydroxyphenyl)- (2-ethyl-3-benzofuranyl)methanone
Identifiers
CAS number 3562-84-3
ATC code M04AB03
PubChem 2333
Chemical data
Formula C17H12Br2O3 
Mol. mass 424.083 g/mol
SMILES eMolecules & PubChem
Physical data
Melt. point 161–163 °C (322–325 °F)
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?
Legal status
Routes  ?

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]

[edit] 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]

[edit] See also

[edit] References

  1. ^ a b Kumar V, Locuson CW, Sham YY, Tracy TS (October 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. 
  2. ^ Heel RC, Brogden RN, Speight TM, Avery GS (November 1977). "Benzbromarone: a review of its pharmacological properties and therapeutic use in gout and hyperuricaemia". Drugs 14 (5): 349–66. PMID 338280. 
  3. ^ Masbernard A, Giudicelli CP (May 1981). "Ten years' experience with benzbromarone in the management of gout and hyperuricaemia". S. Afr. Med. J. 59 (20): 701–6. PMID 7221794. 
  4. ^ Perez-Ruiz F, Alonso-Ruiz A, Calabozo M, Herrero-Beites A, García-Erauskin G, Ruiz-Lucea E (September 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. 
  5. ^ Reinders MK, van Roon EN, Houtman PM, Brouwers JR, Jansen TL (September 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. 
  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 (April 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. 
  8. ^ Hummel MA, Locuson CW, Gannett PM, et al (September 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. 
  9. ^ Locuson CW, Rock DA, Jones JP (June 2004). "Quantitative binding models for CYP2C9 based on benzbromarone analogues". Biochemistry 43 (22): 6948–58. doi:10.1021/bi049651o. PMID 15170332. 
  10. ^ Locuson CW, Suzuki H, Rettie AE, Jones JP (December 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. 
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Antigout preparations (M04)
Uricosuric
Probenecid, Sulfinpyrazone, Benzbromarone, Isobromindione
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