Benzbromarone

  • CAT Number: A000947
  • CAS Number: 3562-84-3
  • Molecular Formula: C17H12Br2O3
  • Molecular Weight: 424.1
  • Purity: ≥95%
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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 xanthine oxidase inhibitor but not uricosuric, and probenecid, another uricosuric drug.

Catalog Number A000947
CAS Number 3562-84-3
Molecular Formula

C17H12Br2O3

Purity 95%
Storage -20°C
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
InChIKey WHQCHUCQKNIQEC-UHFFFAOYSA-N
SMILES CCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)Br)O)Br
Reference

1: Chou HW, Chiu HT, Tsai CW, Ting IW, Yeh HC, Huang HC, Kuo CC; CMUH Kidney
Research Group. Comparative effectiveness of allopurinol, febuxostat and
benzbromarone on renal function in chronic kidney disease patients with
hyperuricemia: a 13-year inception cohort study. Nephrol Dial Transplant. 2017
Nov 17. doi: 10.1093/ndt/gfx313. [Epub ahead of print] PubMed PMID: 29165620.

<br>
2: He L, Li C, Liu X, Yang Q, Zhang H, Xu W, Zhang L, Liu C. Comparative study on
the interaction between 3 CYP2C9 allelic isoforms and benzbromarone by using
LC-MS/MS method. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Dec
1;1070:97-103. doi: 10.1016/j.jchromb.2017.10.051. PubMed PMID: 29100760.
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3: Wang H, Peng Y, Zhang T, Lan Q, Zhao H, Wang W, Zhao Y, Wang X, Pang J, Wang
S, Zheng J. Metabolic Epoxidation Is a Critical Step for the Development of
Benzbromarone-Induced Hepatotoxicity. Drug Metab Dispos. 2017
Dec;45(12):1354-1363. doi: 10.1124/dmd.117.077818. Epub 2017 Oct 11. PubMed PMID:
29021351.
<br>

4: Nicola&#239; J, Thevelin L, Bing Q, Stieger B, Chanteux H, Augustijns P, Annaert P.
Role of the OATP Transporter Family and a Benzbromarone-SensitiveEfflux
Transporter in the Hepatocellular Disposition of Vincristine. Pharm Res. 2017
Nov;34(11):2336-2348. doi: 10.1007/s11095-017-2241-0. Epub 2017 Aug 21. PubMed
PMID: 28828541.
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5: Yoshida M, Cho N, Akita H, Kobayashi K. Association of a reactive intermediate
derived from 1/’,6-dihydroxy metabolite with benzbromarone-induced hepatotoxicity.
J Biochem Mol Toxicol. 2017 Oct;31(10). doi: 10.1002/jbt.21946. Epub 2017 Jun 9.
PubMed PMID: 28598529.
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6: Lin HC, Daimon M, Wang CH, Ho Y, Uang YS, Chiang SJ, Wang LH. Allopurinol,
benzbromarone and risk of coronary heart disease in gout patients: A
population-based study. Int J Cardiol. 2017 Apr 15;233:85-90. doi:
10.1016/j.ijcard.2017.02.013. Epub 2017 Feb 13. PubMed PMID: 28202260.
<br>

7: Cho N, Kobayashi K, Yoshida M, Kogure N, Takayama H, Chiba K. Identification
of novel glutathione adducts of benzbromarone in human liver microsomes. Drug
Metab Pharmacokinet. 2017 Feb;32(1):46-52. doi: 10.1016/j.dmpk.2016.10.412. Epub
2016 Oct 27. PubMed PMID: 28131653.
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8: Wang H, Feng Y, Wang Q, Guo X, Huang W, Peng Y, Zheng J. Cysteine-Based
Protein Adduction by Epoxide-Derived Metabolite(s) of Benzbromarone. Chem Res
Toxicol. 2016 Dec 19;29(12):2145-2152. Epub 2016 Dec 1. PubMed PMID: 27989145.
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9: Zhou Q, Su J, Zhou T, Tian J, Chen X, Zhu J. A study comparing the safety and
efficacy of febuxostat, allopurinol, and benzbromarone in Chinese gout patients:
a retrospective cohort study&#8233;. Int J Clin Pharmacol Ther. 2017 Feb;55(2):163-168.
doi: 10.5414/CP202629. PubMed PMID: 27936522.
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10: Kojima S, Kojima S, Hifumi A, Soejima H, Ogawa H. Therapeutic strategy for
efficient reduction of serum uric acid levels with allopurinol versus
benzbromarone in hyperuricemic patients with essential hypertension – A
randomized crossover study (terao study). Int J Cardiol. 2016 Dec 1;224:437-439.
doi: 10.1016/j.ijcard.2016.09.073. Epub 2016 Sep 24. PubMed PMID: 27701062.

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