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Benzbromarone

Benzbromarone structure

CAS No:
3562-84-3
Formula:
C17H12Br2O3
Chemical Name:
Benzbromarone
Synonyms:
Methanone,(3,5-dibromo-4-hydroxyphenyl)(2-ethyl-3-benzofuranyl)-;Ketone,3,5-dibromo-4-hydroxyphenyl 2-ethyl-3-benzofuranyl;(3,5-Dibromo-4-hydroxyphenyl)(2-ethyl-3-benzofuranyl)methanone;Benzbromarone;3,5-Dibromo-4-hydroxyphenyl 2-ethyl-3-benzofuranyl ketone;2-Ethyl-3-(3,5-dibromo-4-hydroxybenzoyl)benzofuran;L 2214;Benzbromaron;Minuric;Uricovac;Desuric;L 2214-Labaz;Normurat;Azubromaron;Max-Uric;Besuric;MJ 10061;Urinorm;Narcaricin;NSC 85433;(3,5-Dibromo-4-hydroxyphenyl)(2-ethylbenzofuran-3-yl)methanone;(3,5-Dibromo-4-hydroxyphenyl)-(2-ethyl-1-benzofuran-3-yl)methanone
Categories:
Active Pharmaceutical Ingredients > Antipyretic Analgesics

Description

Benzbromarone is a highly effective and well tolerated non-competitive inhibitor of xanthine oxidase, used as an uricosuric agent, used in the treatment of gout.

Solid

Benzbromarone is 1-Benzofuran substituted at C-2 and C-3 by an ethyl group and a 3,5-dibromo-4-hydroxybenzoyl group respectively. An inhibitor of CYP2C9, it is used as an anti-gout medication. It has a role as a uricosuric drug. It is a member of 1-benzofurans and an aromatic ketone. It derives from a 2,6-dibromophenol.|Benzbromarone has been used in trials studying the basic science and treatment of Heart Failure, Hyperuricemia, Chronic Kidney Disease, Abnormal Renal Function, and Gout and Asymptomatic Hyperuricemia.|Benzbromarone is a nonpurine xanthine oxidase inhibitor used for the treatment of gout, but never approved for use in the United States because of concerns over reports of acute liver injury and deaths with its use.|Uricosuric that acts by increasing uric acid clearance. It is used in the treatment of gout.

Benzbromarone Basic Attributes

Molecular Weight：

424.08

Exact Mass：

424.08

EC Number：

222-630-7

UNII：

4POG0RL69O

NSC Number：

759281|85433

DSSTox ID：

DTXSID4022652

ATC Code：

M - Musculo-skeletal system

HScode：

2932999099

Characteristics

PSA：

50.4

XLogP3：

6.64

Appearance：

Solid

Density：

1.7±0.1 g/cm3

Melting Point：

151 °C

Boiling Point：

514.1±50.0 °C at 760 mmHg

Flash Point：

264.7±30.1 °C

Refractive Index：

1.673

Storage Conditions：

2-8°C

Toxicity：

LD50 oral in rat: 248mg/kg

Collision Cross Section：

176 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

safety instructions：

RTECS Number：

OB1804200

Marks：

Precautionary statement(s)：

Missing Phrase - N15.00950417

Hazard Statements：

H301

GHS Classification：

|Danger|H301 (98.11%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P264, P270, P273, P281, P301+P310, P308+P313, P321, P330, P391, P405, and P501|Aggregated GHS information provided by 53 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Hepatotoxicity：

Liver test abnormalities have been reported to occur rarely during benzbromarone therapy, in only 0.1% of patients in clinical trials. Furthermore, it was used widely for many years without reports of hepatotoxicity until the late 1980s, after which several cases of acute liver injury and acute liver failure during benzbromarone therapy were published. Hepatic injury arises after 1 to 6 months of therapy presenting with jaundice and fatigue, usually with a hepatocellular pattern of enzyme elevations. Immunoallergic symptoms (rash, fever) are uncommon. Low levels of autoantibodies have been reported in some cases with liver histology demonstrating chronic active hepatitis, particularly if benzbromarone is not stopped promptly. Upon stopping therapy, resolution is typically within 1 to 3 months. The hepatic injury from benzbromarone is similar to that reported with benzarone, a structurally related drug that was used for peripheral vascular disease, but also withdrawn also because of concerns over hepatotoxicity.

Drug Information

LiverTox Summary：

Benzbromarone is a nonpurine xanthine oxidase inhibitor used for the treatment of gout, but never approved for use in the United States because of concerns over reports of acute liver injury and deaths with its use.

MeSH：

Gout suppressants that act directly on the renal tubule to increase the excretion of uric acid, thus reducing its concentrations in plasma. (See all compounds classified as Uricosuric Agents.)

MeSH Entry Terms：

Acifugan

Benzbromarone Use and Manufacturing

Uses

Coronarodilatator;Uric acid transport inhibitor

Manufacturing Info：

Methanone, (3,5-dibromo-4-hydroxyphenyl)(2-ethyl-3-benzofuranyl)-: INACTIVE

Computed Properties

Molecular Weight:424.1
XLogP3:5.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:423.91327
Monoisotopic Mass:421.91532
Topological Polar Surface Area:50.4
Heavy Atom Count:22
Complexity:405
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is a benzofuran derivative and a uricosuric drug. Its mechanism of action is mainly to inhibit the reabsorption of uric acid by the renal tubules, thereby reducing the concentration of uric acid in the blood.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Benzbromarone Tablets
Ingredients	The main component of this product is benzbromarone. Chemical name: 3,5-dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl-ketone Molecular weight: C17H12Br2O3
Indication	The uricosuric effect of benzbromarone may be attenuated by salicylates and sulfinpyrazone.
Specifications	50 mg

Benzbromarone Tablets
Ingredients	Benzene bromide
Indication	The effect of benzbromarone in promoting uric acid excretion can be weakened by salicylates and sulfinpyrazone.

Benzbromarone Tablets
Ingredients	The main ingredient of this product is benzbromarone.
Indication	The uricosuric effect of benzbromarone may be attenuated by salicylates and sulfinpyrazone.
Specifications	50 mg
Manufacturer	Yichang HEC Changjiang Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

Inner Mongolia Kangpu Pharmaceutical Co., Ltd.

China
Active
Zhejiang Chemsyn Pharm Co., Ltd.

China
Active
Yichang HEC Changjiang Pharmaceutical Co., Ltd.

China
Active

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