Lesinurad

Base Information

• Chemical Name: Lesinurad
• CAS No.: 878672-00-5
• Molecular Formula: C₁₇H₁₄BrN₃O₂S
• Molecular Weight: 404.287
• European Community (EC) Number: 689-245-8
• UNII: 09ERP08I3W,Q59CAT99RS,73WY698HZ7
• DSSTox Substance ID: DTXSID201026091
• Wikipedia: Lesinurad
• Wikidata: Q21820633
• NCI Thesaurus Code: C175109
• Pharos Ligand ID: KUT3SVC6AMQ7
• Metabolomics Workbench ID: 152716
• ChEMBL ID: CHEMBL2105720
• Mol file: 878672-00-5.mol

Synonyms:((5-bromo-4-(4-cyclopropyl-1-naphthyl)-4H-1,2,4-triazol-3-yl)sulfanyl)acetic acid;lesinurad;RDEA594;Zurampic

Chemical Property of Lesinurad

Chemical Property:

• Melting Point: >171oC (dec.)
• Boiling Point: 643.7±65.0 °C(Predicted)
• PKA: 2.91±0.10(Predicted)
• PSA: 93.31000
• Density: 1.72±0.1 g/cm3(Predicted)
• LogP: 4.23710
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 402.99901
• Heavy Atom Count: 24
• Complexity: 479

Purity/Quality:

98%min ^*data from raw suppliers

Lesinurad ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antigout Agents
• Canonical SMILES: C1CC1C2=CC=C(C3=CC=CC=C23)N4C(=NN=C4Br)SCC(=O)O
• Recent ClinicalTrials: A Phase 4 Safety and Efficacy Study to Evaluate Lesinurad 200 mg in Participants With Gout and Renal Impairment
• Recent EU Clinical Trials: A Phase 4, Randomized, Double-Blind, Multicenter, Placebo-Controlled Study to Evaluate the Safety and Efficacy of Lesinurad 200 mg in Combination With a Xanthine Oxidase Inhibitor (XOI), Compared With an XOI Alone, in Subjects With Gout and Estimated Creatinine Clearance 30 to <60 mL/min Who Have Not Achieved Target Serum Uric Acid Levels on an XOI Alone
• Description: Approved by the FDA late in 2015, lesinurad is an urate anion exchange transporter 1 (URAT1) inhibitor for use in the treatment of gout. Ardea Biosciences, which is a subsidiary of AstraZeneca, developed lesinurad to be used in a combination therapy with xanthine oxidase inhibitors for the treatment of hyperuricaemia associated with gout. The approval process is ongoing in several other countries across the globe, with the EMA Committee for Medicinal Products for Human Use giving lesinurad a positive opinion for use as an adjunctive therapy in combination with xanthine oxidase inhibitors to treat hyperuricaemia.
• Uses: Lesinurad is used to synthesize febuxostat which is a non-purine analog inhibitor of xanthine oxidase. Febuxostat is approved by the European Medicines Agency and the US Food and Drug Administration for treating gout.

Technology Process of Lesinurad

There total 116 articles about Lesinurad 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%

2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid dicyclohexylamine → 2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid (878672-00-5)

Guidance literature:

With sodium hydrogensulfite; In dichloromethane; at 20 ℃; for 2h;

Reference yield: 96.0%

2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid ethyl ester (1158970-52-5) → 2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid (878672-00-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 10 - 15 ℃; Reagent/catalyst;

Reference yield: 93.0%

phenyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate → 2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid (878672-00-5)

Guidance literature:

With sodium hydrogencarbonate; In acetone; at 65 ℃; for 12h;

upstream raw materials:

VRX-480773

1-cyclopropyl-naphthalene

1-Bromonaphthalene

1-amino-4-cyclopropylnaphthalene

Refernces

• 1、 -. "RESOLUTION METHOD FOR AXIS CHIRAL ENANTIOMERS OF LESINURAD". . . Retrieved 2021/02/26.
• 2、 -. "Refining method of Lesinured". Paragraph 0032-0033. . Retrieved 2020/06/05.