Benzbromarone

Base Information

• Chemical Name: Benzbromarone
• CAS No.: 3562-84-3
• Molecular Formula: C17H12Br2O3
• Molecular Weight: 424.088
• Hs Code.: 2932190090
• European Community (EC) Number: 222-630-7
• NSC Number: 759281,85433
• UNII: 4POG0RL69O
• DSSTox Substance ID: DTXSID4022652
• Nikkaji Number: J3.404E
• Wikipedia: Benzbromarone
• Wikidata: Q410435
• NCI Thesaurus Code: C74412
• Pharos Ligand ID: L1B5DR6HXMQL
• Metabolomics Workbench ID: 49569
• ChEMBL ID: CHEMBL388590
• Mol file: 3562-84-3.mol

Synonyms:Acifugan;AL, Benzbromaron;Benzbromaron;Benzbromaron AL;Benzbromaron ratiopharm;Benzbromaron-ratiopharm;Benzbromarone;Besuric;Desuric;Narcaricin;Urinorm

Chemical Property of Benzbromarone

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Melting Point: 161 - 163oC
• Refractive Index: 1.6010 (estimate)
• Boiling Point: 514.1 °C at 760 mmHg
• PKA: 4.66±0.25(Predicted)
• Flash Point: 264.7 °C
• PSA: 50.44000
• Density: 1.709 g/cm³
• LogP: 5.45680
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, freely soluble in acetone and in methylene chloride, sparingly soluble in ethanol (96 per cent).
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 423.91327
• Heavy Atom Count: 22
• Complexity: 405

Purity/Quality:

99% ^*data from raw suppliers

Benzbromarone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)Br)O)Br
• Recent ClinicalTrials: SGLT2 Inhibition: Uric Acid Excretion Study
• Recent EU Clinical Trials: The Gout TrEatment STrategy Project (GO TEST) Overture trial
• Recent NIPH Clinical Trials: Urate lowering drugs RandomIzed parallel-group Comparison study in the Chronic Kidney Disease patients with hypertension and hyperuricemia
• Description: Benzbromarone,a non-competitive inhibitor of xanthine oxidase，is apotent uricosuric drug used in the treatment of gout.Benzbromarone is a benzofuran derivative chemically related to amiodarone. It increases uric acid excretion by non-specificallyinhibiting its tubular reabsorption.lt is used in patients with venous disorders to prevent,retard,or reverse varicose degenerative changes in the vessel wall.Benzbromarone causes diarrhea (3-4% of patients), urate and oxalate stones,urinary sand,renal colic，and allergy in a small number of patients.Liver damage, which reverses after withdrawal, has been described (SEDA-18,108).
• Uses: Benzbromarone is a benzofuran derivative that has been reported to lower serum urate levels in animals and human studies. In normal and hyperuricaemic subjects, benzbromarone reduced serum uric acid levels by one-third to one-half. In comparison with other urate-lowering drugs, 80 mg of micronized or 100 mg of nonmicronized benzbromarone had equal urate-lowering activity to 1–1.5 g of probenecid or 400–800 mg of sulfinpyrazone. The mechanism of the urate-lowering activity of benzbromarone appears to be attributable to its uricosuric activity. In rats, benzobromarone inhibited urate reabsorption in the proximal tubules when given at 10 mg/kg i.v. In isolated rat liver preparation, benzbromarone inhibits xanthine oxidase in vitro but not in vivo . In humans, this compound only weakly inhibits xanthine oxidase and no increase in urinary excretion of xanthine or hypoxanthine was observed. After oral administration, about 50% of benzbromarone is absorbed. The drug undergoes extensive dehalogenation in the liver and is excreted mainly in the bile and feces. For control of gout the usual therapeutic dose is 100–200 mg daily. Benzbromarone has few side effects and is usually well tolerated. Benzbromarone is a uricosuric agent used in the treatment of gout and hyperuricemia. Studies show that use of Benzbromarone results in less complications than other uricosuric agent such as Allopurinol. Coronarodilatator;Uric acid transport inhibitor
• Therapeutic Function: Uricosuric, Antiarthritic

Technology Process of Benzbromarone

There total 11 articles about Benzbromarone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

benzarone (1477-19-6) → benzbromarone (3562-84-3)

Guidance literature:

With bromine; acetic acid; In water; at 20 ℃; for 2h;

DOI:10.1021/acs.joc.9b00270

Reference yield:

benzarone (1477-19-6) → benziodarone (68-90-6) + benzbromarone (3562-84-3)

Guidance literature:

Reference yield:

2-ethylbenzofuran (3131-63-3) → benzbromarone (3562-84-3)

Guidance literature:

Multi-step reaction with 3 steps

1: tin (IV)-chloride; carbon disulfide

2: pyridine hydrochloride

3: aqueous acetic acid; bromine

With carbon disulfide; bromine; pyridine hydrochloride; tin(IV) chloride; acetic acid;

upstream raw materials:

benzarone

2-ethylbenzofuran

(2-ethylbenzofuran-3-yl)(4-methoxyphenyl)methanone

4-methoxy-benzoyl chloride

Downstream raw materials:

benzbromarone methyl ether

benzarone

4-[2,6-Dibromo-4-(2-ethyl-benzofuran-3-carbonyl)-phenoxysulfonyl]-2-hydroxy-benzoic acid

Refernces

• 1、 Huang, Wenbo,Xu, Jing,Liu, Changhui,Chen, Zhiyan,Gu, Yanlong. "Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds". . p. 2941 - 2950. Retrieved 2019/02/26.
• 2、 Wempe, Michael F.,Jutabha, Promsuk,Quade, Bettina,Iwen, Timothy J.,Frick, Morin M.,Ross, Ian R.,Rice, Peter J.,Anzai, Naohiko,Endou, Hitoshi. "Developing potent human uric acid transporter 1 (hURAT1) inhibitors". experimental part. p. 2701 - 2713. Retrieved 2011/06/25.