Triclabendazole

Base Information

• Chemical Name: Triclabendazole
• CAS No.: 68786-66-3
• Molecular Formula: C14H9Cl3N2OS
• Molecular Weight: 359.663
• Hs Code.: 29339900
• European Community (EC) Number: 614-728-7
• NSC Number: 759250
• UNII: 4784C8E03O
• DSSTox Substance ID: DTXSID7043952
• Nikkaji Number: J126.317J
• Wikipedia: Triclabendazole
• Wikidata: Q419739
• NCI Thesaurus Code: C75236
• RXCUI: 2118525
• Metabolomics Workbench ID: 153271
• ChEMBL ID: CHEMBL1086440
• Mol file: 68786-66-3.mol

Synonyms:6-chloro-5-(2,3-dichlorophenoxy)-2-methylthiobenzimidazole;Egaten;Fasicare;Fasinex;Flukare;Tremacide;triclabendazole

Chemical Property of Triclabendazole

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 5.68E-10mmHg at 25°C
• Melting Point: 175-176 °C
• Refractive Index: 1.724
• Boiling Point: 495.9 °C at 760 mmHg
• PKA: 7.91±0.10(Predicted)
• Flash Point: 253.7 °C
• PSA: 63.21000
• Density: 1.59 g/cm³
• LogP: 6.03730
• Storage Temp.: 0-6°C
• Solubility.: Acetonitrile (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 357.950117
• Heavy Atom Count: 21
• Complexity: 365

Purity/Quality:

99%min ^*data from raw suppliers

Triclabendazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Anthelmintic Agents
• Canonical SMILES: CSC1=NC2=CC(=C(C=C2N1)Cl)OC3=C(C(=CC=C3)Cl)Cl
• Recent ClinicalTrials: Compassionate Use of Triclabendazole for the Treatment of Parasites (Prior to FDA Approval; Expanded Access Program)
• Description: Triclabendazole is a benzimidazole anthelmintic. It eliminates both immature and adult flukes in a sheep model of F. hepatica infection when administered at a dose of 10 mg/kg. Triclabendazole (5 μM) also protects against glucose- or α-synuclein-induced apoptosis in S. cerevisiae via inhibition of adenylyl cyclase in the Ras-adenylyl cyclase-protein kinase A (PKA) nutrient sensing pathway.
• Uses: An anthelmintic (fasciola) Triclabendazole is classified under the category of ‘Anthelmintic flukicide for veterinary use. An anthelmintic (fasciola).

Technology Process of Triclabendazole

There total 24 articles about Triclabendazole 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: 94.0%

5-chloro-6-(2,3-dichlorophenoxy)-2,3-dihydro-1H-1,3-benzodiazole-2-thione (68828-69-3) + methyl iodide (74-88-4) → triclabendazole (68786-66-3)

Guidance literature:

With potassium hydroxide; In ethanol; water; at 10 - 50 ℃; for 20h;

Reference yield: 92.0%

5-chloro-6-(2,3-dichlorophenoxy)-2,3-dihydro-1H-1,3-benzodiazole-2-thione (68828-69-3) + methyl iodide (74-88-4) → 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzo[d]imidazole (68786-66-3)

Guidance literature:

With potassium hydroxide; In ethanol; water; a) r.t., 30 min, b) 50 deg C, 1 h;

DOI:10.1039/P19920003129

Reference yield: 81.7%

6-chloro-5-(2,3-dichlorophenoxy)-1H-benzimidazole-2-thiol (68828-69-3) + dimethyl sulfate (77-78-1) → triclabendazole (68786-66-3)

Guidance literature:

6-chloro-5-(2,3-dichlorophenoxy)-1H-benzimidazole-2-thiol; dimethyl sulfate; In methanol; water; at 60 ℃; for 0.5h;

With sodium carbonate; In water; at 60 ℃; for 1.5h;

upstream raw materials:

5-chloro-6-(2,3-dichlorophenoxy)-2,3-dihydro-1H-1,3-benzodiazole-2-thione

methyl iodide

4-chloro-5-(2,3-dichlorophenoxy)-1,2-phenylenediamine

6-chloro-5-(2,3-dichlorophenoxy)-1H-benzimidazole-2-thiol

Downstream raw materials:

6-chloro-5-(2,3-dichlorophenoxy)-1-methyl-2-methylthio-1H-benzimidazole

Triclabendazole sulfoxide

Refernces

• 1、 -. "Synthesis method of triclabendazole". Paragraph 0025-0031. . Retrieved 2019/01/13.
• 2、 -. "PROCESS FOR PREPARATION OF TRICLABENDAZOLE". . . Retrieved 2013/11/19.