Benzbromarone
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 326875

CAS#: 3562-84-3

Description: 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.


Price and Availability

Size
Price

500mg
USD 150
5g
USD 650
Size
Price

1g
USD 250
10g
USD 950
Size
Price

2g
USD 450

Benzbromarone, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326875
Name: Benzbromarone
CAS#: 3562-84-3
Chemical Formula: C17H12Br2O3
Exact Mass: 421.9153
Molecular Weight: 424.088
Elemental Analysis: C, 48.15; H, 2.85; Br, 37.68; O, 11.32


Synonym: L2214; L 2214; L-2214; L2214-Labaz; MJ 10061; Narcaricin; Normurat; Benzbromarone.

IUPAC/Chemical Name: (3,5-dibromo-4-hydroxyphenyl)(2-ethylbenzofuran-3-yl)methanone

InChi Key: WHQCHUCQKNIQEC-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: O=C(C1=CC(Br)=C(O)C(Br)=C1)C2=C(CC)OC3=CC=CC=C23


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Stamp LK, Haslett J, Frampton C, White D, Gardner D, Stebbings S, Taylor G, Grainger R, Kumar R, Kumar S, Kain T, Porter D, Corkill M, Cathro A, Metcalfe S, Wyeth J, Dalbeth N. The safety and efficacy of benzbromarone in gout in Aotearoa New Zealand. Intern Med J. 2016 Jul 8. doi: 10.1111/imj.13173. [Epub ahead of print] PubMed PMID: 27391386.

2: López LC, Varea O, Navarro S, Carrodeguas JA, Sanchez de Groot N, Ventura S, Sancho J. Benzbromarone, Quercetin, and Folic Acid Inhibit Amylin Aggregation. Int J Mol Sci. 2016 Jun 18;17(6). pii: E964. doi: 10.3390/ijms17060964. PubMed PMID: 27322259; PubMed Central PMCID: PMC4926496.

3: Ahn SO, Ohtomo S, Kiyokawa J, Nakagawa T, Yamane M, Lee KJ, Kim KH, Kim BH, Tanaka J, Kawabe Y, Horiba N. Stronger Uricosuric Effects of the Novel Selective URAT1 Inhibitor UR-1102 Lowered Plasma Urate in Tufted Capuchin Monkeys to a Greater Extent than Benzbromarone. J Pharmacol Exp Ther. 2016 Apr;357(1):157-66. doi: 10.1124/jpet.115.231647. Epub 2016 Feb 23. PubMed PMID: 26907620.

4: Wang K, Wang H, Peng Y, Zheng J. Identification of Epoxide-Derived Metabolite(s) of Benzbromarone. Drug Metab Dispos. 2016 Apr;44(4):607-15. doi: 10.1124/dmd.115.066803. Epub 2016 Jan 20. PubMed PMID: 26792818.

5: Masubuchi Y, Kondo S. Inactivation of CYP3A4 by Benzbromarone in Human Liver Microsomes. Drug Metab Lett. 2016;10(1):16-21. PubMed PMID: 26693855.

6: Shirakawa M, Sekine S, Tanaka A, Horie T, Ito K. Metabolic activation of hepatotoxic drug (benzbromarone) induced mitochondrial membrane permeability transition. Toxicol Appl Pharmacol. 2015 Oct 1;288(1):12-8. doi: 10.1016/j.taap.2015.06.018. Epub 2015 Jul 3. PubMed PMID: 26148448.

7: Kitagawara Y, Ohe T, Tachibana K, Takahashi K, Nakamura S, Mashino T. Novel Bioactivation Pathway of Benzbromarone Mediated by Cytochrome P450. Drug Metab Dispos. 2015 Sep;43(9):1303-6. doi: 10.1124/dmd.115.065037. Epub 2015 Jun 23. PubMed PMID: 26106235.

8: Manger B. [Uricosuric agent benzbromarone vs. allopurinol: comparable effect]. Dtsch Med Wochenschr. 2015 Apr;140(8):562. doi: 10.1055/s-0041-101396. Epub 2015 Apr 16. German. PubMed PMID: 25945905.

9: Kadowaki D, Sakaguchi S, Miyamoto Y, Taguchi K, Muraya N, Narita Y, Sato K, Chuang VT, Maruyama T, Otagiri M, Hirata S. Direct radical scavenging activity of benzbromarone provides beneficial antioxidant properties for hyperuricemia treatment. Biol Pharm Bull. 2015;38(3):487-92. doi: 10.1248/bpb.b14-00514. Epub 2015 Jan 15. PubMed PMID: 25757933.

10: Felser A, Lindinger PW, Schnell D, Kratschmar DV, Odermatt A, Mies S, Jenö P, Krähenbühl S. Hepatocellular toxicity of benzbromarone: effects on mitochondrial function and structure. Toxicology. 2014 Oct 3;324:136-46. doi: 10.1016/j.tox.2014.08.002. Epub 2014 Aug 7. PubMed PMID: 25108121.

11: Azevedo VF, Buiar PG, Giovanella LH, Severo CR, Carvalho M. Allopurinol, benzbromarone, or a combination in treating patients with gout: analysis of a series of outpatients. Int J Rheumatol. 2014;2014:263720. doi: 10.1155/2014/263720. Epub 2014 Feb 12. PubMed PMID: 24719620; PubMed Central PMCID: PMC3955622.

12: Parashar A, Gade SK, Potnuru M, Madhavan N, Manoj KM. The curious case of benzbromarone: insight into super-inhibition of cytochrome P450. PLoS One. 2014 Mar 3;9(3):e89967. doi: 10.1371/journal.pone.0089967. eCollection 2014. PubMed PMID: 24594849; PubMed Central PMCID: PMC3940698.

13: Pandey RN, Wang TS, Tadjuidje E, McDonald MG, Rettie AE, Hegde RS. Structure-activity relationships of benzbromarone metabolites and derivatives as EYA inhibitory anti-angiogenic agents. PLoS One. 2013 Dec 18;8(12):e84582. doi: 10.1371/journal.pone.0084582. eCollection 2013. PubMed PMID: 24367676; PubMed Central PMCID: PMC3867503.

14: Cheng CL, Chao PH, Hsu JC, Weng MM, On AW, Yang YH. Utilization patterns of antihyperuricemic agents following safety announcement on allopurinol and benzbromarone by Taiwan Food and Drug Administration. Pharmacoepidemiol Drug Saf. 2014 Mar;23(3):309-13. doi: 10.1002/pds.3550. Epub 2013 Dec 5. PubMed PMID: 24307655.

15: Day R, Lee H, Graham G, Williams K. Benzbromarone: availability for general prescribing in New Zealand (a response to letters by Dr Lance Gravatt onbenzbromarone). N Z Med J. 2013 Sep 13;126(1382):124-6. PubMed PMID: 24154781.

16: Dalbeth N, Gow P, Stamp L, Merriman T, Stuart R, Winnard D, Lindsay K; New Zealand Rheumatology Association and the Māori Gout Action Group. New urate-lowering therapies in Aotearoa New Zealand: a response to Dr Lance Gravatt's letter on benzbromarone hepatotoxicity. N Z Med J. 2013 Sep 13;126(1382):120-3. PubMed PMID: 24154780.

17: Gravatt L. Gout--is Lee's 2008 risk:benefit conclusion for benzbromarone hepatotoxicity still relevant today? N Z Med J. 2013 Sep 13;126(1382):118-9. PubMed PMID: 24154779.

18: Gravatt L. Gout--is adequate attention devoted to preventing haemorrhagic risk when benzbromarone is administered with warfarin? N Z Med J. 2013 Sep 13;126(1382):116-7. PubMed PMID: 24154778.

19: Cai HY, Wang T, Zhao JC, Sun P, Yan GR, Ding HP, Li YX, Wang HY, Zhu WL, Chen KX. Benzbromarone, an old uricosuric drug, inhibits human fatty acid binding protein 4 in vitro and lowers the blood glucose level in db/db mice. Acta Pharmacol Sin. 2013 Nov;34(11):1397-402. doi: 10.1038/aps.2013.97. Epub 2013 Sep 30. PubMed PMID: 24077632; PubMed Central PMCID: PMC4651057.

20: Roberts RL, Wallace MC, Wright DF, Cadzow M, Dalbeth N, Jones PB, Stamp LK, Harrison AA, Black MA, Merriman TR. Frequency of CYP2C9 polymorphisms in Polynesian people and potential relevance to management of gout with benzbromarone. Joint Bone Spine. 2014 Mar;81(2):160-3. doi: 10.1016/j.jbspin.2013.07.006. Epub 2013 Aug 7. PubMed PMID: 23932726.