Fenbendazole

Base Information

• Chemical Name: Fenbendazole
• CAS No.: 43210-67-9
• Deprecated CAS: 53571-02-1
• Molecular Formula: C15H13N3O2S
• Molecular Weight: 299.353
• Hs Code.: 29339900
• European Community (EC) Number: 256-145-7
• NSC Number: 757824
• UNII: 621BVT9M36
• DSSTox Substance ID: DTXSID0040672
• Nikkaji Number: J15.833J
• Wikipedia: Fenbendazole
• Wikidata: Q908013
• NCI Thesaurus Code: C75218
• RXCUI: 4325
• Pharos Ligand ID: B8LVFQ13WFKZ
• Metabolomics Workbench ID: 44033
• ChEMBL ID: CHEMBL37161
• Mol file: 43210-67-9.mol

Synonyms:Fenbendazole;Panacur;Phenbendasol

Chemical Property of Fenbendazole

Chemical Property:

• Appearance/Colour: Off-white solid
• Melting Point: 233 °C
• Refractive Index: 1.709
• PKA: 10.80±0.10(Predicted)
• PSA: 92.31000
• Density: 1.4 g/cm³
• LogP: 3.96540
• Storage Temp.: 0-6°C
• Water Solubility.: Insoluble in water
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 299.07284784
• Heavy Atom Count: 21
• Complexity: 363

Purity/Quality:

98% ^*data from raw suppliers

Fenbendazole ^*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

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)NC1=NC2=C(N1)C=C(C=C2)SC3=CC=CC=C3
• Uses: Anthelmintic. Broad-spectrum, high efficiency, low toxicity, antiparasitic. It has a strong killing effect on Roundworm, nematodes, tapeworms, cysticercosis , Fasciola and other parasites, not only killing worms, especially having a great effect on Transitional larvae ehich are hazardous to the liver, lungs and intestines .Fenbendazole is a benzimidazole anthelmintic, not only having a highly anthelmintic activity for gastrointestinal nematodes adults and larvae , but also having a good effect on dictyocaulasis, flukes and tapeworms, in addition,it has a strong killing eggs effect. Fenbendazole is a benzimidazole anthelmintic that is metabolised in mammals to a series of other benzimidazoles including oxfendazole. It is used for the control of gastrointestinal roundworms, lung worms, Nematodes and tape worms. It is the only benzimidazole approved for use in organic livestock production.
• Production method: 5-chloro-2-nitroaniline reacts with benzene thiol, to thereby obtain 5-phenylthio-2-nitroaniline in 91% yield.Generate 3-phenylthio-o-phenylenediamine by ferrous sulfate-iron reduction in 90% yield. Finally, cyclize it with the S-methyl-melamine Methyl to obtain fenbendazole.
• Description: Fenbendazole is a benzimidazole anthelmintic. It is active against Giardia in vitro (IC50 = 0.3 μM). Fenbendazole (20 mg/kg) prevents infiltration of parasites into the brain in a rabbit model of E. cuniculi infection. Fenbendazole also activates HIF-1α and prevents oxidative stress-induced death in primary neurons in vitro.
• Therapeutic Function: Anthelmintic

Technology Process of Fenbendazole

There total 16 articles about Fenbendazole 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: 89.99%

1,2-diamino-4-phenylthiobenzene (43156-48-5) + N-(trichloromethyl)carbamic acid methyl ester → Fenbendazole (43210-67-9)

Guidance literature:

In acetone; at 40 - 60 ℃; for 2.5h; Temperature; Time;

Reference yield: 88.0%

1,2-diamino-4-phenylthiobenzene (43156-48-5) + S-Methylisothiourea sulfate (867-44-7,147895-43-0) + methyl chloroformate (79-22-1) → Fenbendazole (43210-67-9)

Guidance literature:

S-Methylisothiourea sulfate; methyl chloroformate; With sodium hydroxide; In water; at 3 - 6 ℃; for 0.666667h;

1,2-diamino-4-phenylthiobenzene; With acetic acid; In ethanol; water; at 95 ℃; for 24h;

DOI:10.1002/jhet.5570410220

Reference yield: 86.8%

methyl N-methylcarbamate (6642-30-4) + 1,2-diamino-4-phenylthiobenzene (43156-48-5) → fenbendazole (43210-67-9)

Guidance literature:

With hydrogenchloride; In toluene; at 20 - 55 ℃; for 2h;

upstream raw materials:

methyl N-methylcarbamate

1,2-diamino-4-phenylthiobenzene

2,4-dibromonitrobenzene

1.4-dibromobenzene

Downstream raw materials:

oxfendazole

5-(phenylthio)-1H-benzo[d]imidazol-2-amine

Refernces

• 1、 -. "Synthetic method of fenbendazole". . . Retrieved 2021/08/14.
• 2、 Chassaing,Berger,Heckeroth,Ilg,Jaeger,Kern,Schmid,Uphoff. "Highly water-soluble prodrugs of anthelmintic benzimidazole carbamates: Synthesis, pharmacodynamics, and pharmacokinetics". . p. 1111 - 1114. Retrieved 2008/09/20.