Benzbromarone

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Benzbromarone
	Error creating thumbnail: File missing
Clinical data
ATC code	M04AB03 (WHO) ;
Identifiers
	IUPAC name (3,5-dibromo-4-hydroxyphenyl)- (2-ethyl-3-benzofuranyl)methanone;
CAS Number	3562-84-3;
PubChem CID	2333;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C17H12Br2O3
Molar mass	424.083 g/mol
3D model (JSmol)	Interactive image;
Melting point	161 to 163 °C (Expression error: Unrecognized word "to". °F)
	SMILES CCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)Br)O)Br;

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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In 2003, the drug was withdrawn by Sanofi-Synthélabo, after reports of serious hepatotoxicity, although it is still marketed in several countries by other drug companies.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

References

↑ ^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)
↑ 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)
↑ 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)
↑ 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)
↑ 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)
↑ Schepers GW (1981). "Benzbromarone therapy in hyperuricaemia; comparison with allopurinol and probenecid". J. Int. Med. Res. 9 (6): 511–5. PMID 7033016.
↑ 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)
↑ 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)
↑ 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)
↑ 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)
↑ 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

Template:WH Template:WS

[Kumar-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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v t e Antigout preparations (M04)
Uricosuric	Probenecid, Sulfinpyrazone
Other	Allopurinol, Cinchophen, Colchicine, Febuxostat, Oxypurinol

Benzbromarone

Overview

Effect on cytochrome P450

Safety

See also

References

Navigation menu

Clinical data
Error creating thumbnail: File missing
ATC code	M04AB03 (WHO)
Identifiers
IUPAC name (3,5-dibromo-4-hydroxyphenyl)- (2-ethyl-3-benzofuranyl)methanone
CAS Number	3562-84-3
PubChem CID	2333
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₁₇H₁₂Br₂O₃
Molar mass	424.083 g/mol
3D model (JSmol)	Interactive image
Melting point	161 to 163 °C (Expression error: Unrecognized word "to". °F)
SMILES CCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)Br)O)Br

Benzbromarone

Overview

Effect on cytochrome P450

Safety

See also

References

Navigation menu

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