Fexinidazole

Base Information

• Chemical Name: Fexinidazole
• CAS No.: 59729-37-2
• Molecular Formula: C12H13 N3 O3 S
• Molecular Weight: 279.32
• Hs Code.: 2933290090
• European Community (EC) Number: 682-380-3
• UNII: 306ERL82IR
• DSSTox Substance ID: DTXSID00208448
• Nikkaji Number: J18.186B
• Wikipedia: Fexinidazole
• Wikidata: Q5446115
• NCI Thesaurus Code: C65680
• RXCUI: 2564146
• Metabolomics Workbench ID: 153285
• ChEMBL ID: CHEMBL1631694
• Mol file: 59729-37-2.mol

Synonyms:fexinidazole;HOE 239

Chemical Property of Fexinidazole

Chemical Property:

• Vapor Pressure: 4.58E-10mmHg at 25°C
• Boiling Point: 511.3°C at 760 mmHg
• Flash Point: 263.1°C
• PSA: 98.17000
• Density: 1.33g/cm³
• LogP: 3.15240
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 279.06776246
• Heavy Atom Count: 19
• Complexity: 305

Purity/Quality:

97% ^*data from raw suppliers

1-Methyl-2-((4-(methylthio)phenoxy)-methyl)-5-nitro-1H-imidazole 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=CN=C1COC2=CC=C(C=C2)SC)[N+](=O)[O-]
• Recent ClinicalTrials: A Pharmacokinetic and Tolerability Study of Fexinidazole in a Single Oral Dose in Adult Participants With Mild and Moderate Hepatic Impairment
• Recent EU Clinical Trials: Phase 2 Randomized, Multicenter, Double-blinded Safety and Efficacy Study to Evaluate Oral Fexinidazole Dosing Regimens for the Treatment of Adult Patients with Chronic Indeterminate Chagas Disease
• Uses: Fexinidazole is a medication used in the treatment of African trypanosomiasis caused by trypanosoma brucei gambiense. An antitrypanosomal agent. It also functions as a medication used against the main species that cause visceral and cutaneous new World leishmaniasis.

Technology Process of Fexinidazole

There total 8 articles about Fexinidazole 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: 82.0%

C13H14N2O3S → 1-methyl-2-{[(4-methylsulfanyl)phenoxy]methyl}-5-nitro-1H-imidazole (59729-37-2)

Guidance literature:

With nitronium tetrafluoborate; silver carbonate; In N,N-dimethyl acetamide; at 90 ℃; for 12h; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.5b02133

Reference yield: 70.0%

→ 1-methyl-2-{[(4-methylsulfanyl)phenoxy]methyl}-5-nitro-1H-imidazole (59729-37-2)

Guidance literature:

Reference yield: 67.5%

1-methyl-2-(4-methylmercaptophenyloxymethyl)-5-nitroimidazole hydrochloride (1610877-02-5) → 1-methyl-2-{[(4-methylsulfanyl)phenoxy]methyl}-5-nitro-1H-imidazole (59729-37-2)

Guidance literature:

With ammonium hydroxide; In acetone; at 52 ℃;

upstream raw materials:

dimethyl sulfate

1-methyl-5-nitro-2-(4-thiocyanato-phenoxymethyl)-1H-imidazole

4-hydroxythioanisole

2-(chloromethyl)-1-methyl-5-nitroimidazole

Downstream raw materials:

1-methyl-2-(4-methylmercaptophenyloxymethyl)-5-nitroimidazole hydrochloride

1-methyl-2-(4-methylsulfinylphenoxymethyl)-5-nitroimidazole