Mebendazole

Base Information

• Chemical Name: Mebendazole
• CAS No.: 31431-39-7
• Molecular Formula: C16H13N3O3
• Molecular Weight: 295.298
• Hs Code.: 29339900
• European Community (EC) Number: 250-635-4
• NSC Number: 757838,184849
• UNII: 81G6I5V05I
• DSSTox Substance ID: DTXSID4040682
• Nikkaji Number: J2.773A
• Wikipedia: Mebendazole
• Wikidata: Q422194
• NCI Thesaurus Code: C47595
• RXCUI: 6672
• Metabolomics Workbench ID: 42964
• ChEMBL ID: CHEMBL685
• Mol file: 31431-39-7.mol

Synonyms:Anti Worm;Anti-Worm;Bantenol;Banworm;Boots Threadworm Treatment;Lomper;Madicure;Mebendan;Mebendazole;Mebenvet;Pripsen Mebendazole;R17635;Sqworm;Sufil;Surfont;Telmin;Vermicol;Vermidil;Vermox;Wormkuur

Chemical Property of Mebendazole

Chemical Property:

• Appearance/Colour: white to yellowish powder
• Melting Point: 288.5 °C
• Refractive Index: 1.702
• Boiling Point: 436.98°C (rough estimate)
• PKA: pKa 3.43/9.93(H2O,t =25,I=0.025) (Uncertain)
• PSA: 84.08000
• Density: 1.388 g/cm³
• LogP: 3.04520
• Storage Temp.: 0-6°C
• Solubility.: Practically insoluble in water, in alcohol and in methylene chloride.
• Water Solubility.: 35.4mg/L(25 oC)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 295.09569129
• Heavy Atom Count: 22
• Complexity: 423

Purity/Quality:

99% ^*data from raw suppliers

Mebendazole ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Anthelmintic Agents
• Canonical SMILES: COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C3=CC=CC=C3
• Recent ClinicalTrials: A Phase I Study of Mebendazole for the Treatment of Pediatric Gliomas
• Recent EU Clinical Trials: A phase 2a TDM-guided clinical study on the safety and efficacy of mebendazole in patients with advanced gastrointestinal cancer or cancer of unknown origin
• Indications: Mebendazole is the drug of choice for mixed nematode infections due to Trichuris trichiura, Ascaris lumbricoides, Enterobius vermicularis, Capillaria philippinensis or hookworms. The drug may be used against hydatid disease when albendazole is not available. Unlike thiabendazole, mebendazole (Vermox) does not inhibit fumarate reductase.While mebendazole binds to both mammalian and nematode tubulin, it exhibits a differential affinity for the latter, possibly explaining the selective action of the drug. The selective binding to nematode tubulin may inhibit glucose absorption, leading to glycogen consumption and ATP depletion.
• Description: Mebendazole is a broad-spectrum anthelmintic that is active against both larval and adult stages of nematodes selectively binding the β-subunit of tubulin, thereby inhibiting intestinal microtubule synthesis in the parasite (IC50 = 0.19 μM for Giardia in vitro). As a tubulin-binding agent, mebendazole also possesses antitumor properties, inducing apoptosis of various human carcinomas both in vitro and in vivo, thus preventing their growth and migration. Furthermore, mebendazole has been used to inhibit hedgehog signaling in cancer cells via suppression of the formation of the primary cilium, a microtubule-based organelle that functions as a signaling hub for hedgehog pathway activation. Additionally, mebendazole has been shown to stabilize the transcriptional activator HIF-1α and its downstream targets, abrogating oxidative neuronal death in primary neurons.
• Uses: Mebendazole Polymorph C is an Anthelmintic (Nematodes). Anthelmintic (Nematodes) For the treatment of Enterobius vermicularis (pinworm), Trichuris trichiura (whipworm), Ascaris lumbricoides (common roundworm), Ancylostoma duodenale (common hookworm), Necator americanus (American hookworm) in single or mixed infections.
• Therapeutic Function: Anthelmintic
• Clinical Use: Methyl 5-benzoyl-2-benzimidazolecarbamate (Vermox) isa broad-spectrum anthelmintic that is effective against variousnematode infestations, including whipworm, pinworm,roundworm, and hookworm. Mebendazole irreversiblyblocks glucose uptake in susceptible helminths, thereby depletingglycogen stored in the parasite. It apparently does notaffect glucose metabolism in the host. It also inhibits cell divisionin nematodes.Mebendazole is poorly absorbed by the oral route.Adverse reactions are uncommon and usually consist of abdominaldiscomfort. It is teratogenic in laboratory animalsand, therefore, should not be given during pregnancy. Mebendazole is used primarily for the treatment of A. lumbricoides, T. trichiura, E. vermicularis, and hookworm infections, in which it produces high cure rates. It is an alternative agent for the treatment of trichinosis and visceral larva migrans. Owing to its broad-spectrum anthelmintic effect, mixed infections (ascariasis, hookworm infestation, or enterobiasis in association with trichuriasis) frequently respond to therapy. High doses have been used to treat hydatid disease, but albendazole is now thought to be superior. Intestinal nematode infections Trichinosis (larval stage)
• Drug interactions: Potentially hazardous interactions with other drugs Cimetidine: possibly inhibits metabolism of mebendazole. Antiepileptics: phenytoin, carbamazepine and phenobarbital: lower mebendazole concentrations, only relevant when being used in high doses for echinococcosis.

Technology Process of Mebendazole

There total 16 articles about Mebendazole 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: 95.0%

4-benzoylbenzene-1,2-diamine (39070-63-8) + O-methyl-N-(methoxycarbonyl)-isourea (40943-37-1) → mebendazole (31431-39-7)

Guidance literature:

With acetic acid; In toluene;

Reference yield: 88.0%

(2-amino-1H-benzo[d]imidazol-6-yl)(phenyl)methanone (52329-60-9) + methyl chloroformate (79-22-1) → mebendazole (31431-39-7)

Guidance literature:

With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide; In N,N-dimethyl-formamide; at 120 ℃; for 24h;

DOI:10.1039/c8ob02172d

Reference yield:

methyl-N-cyano carbamate (21729-98-6) + 4-benzoylbenzene-1,2-diamine (39070-63-8) → mebendazole (31431-39-7)

Guidance literature:

With hydrogenchloride; In water; acetone; at 97 ℃; for 5.16h; Temperature;

upstream raw materials:

(2-amino-1H-benzimidazol-5-yl)(phenyl)methanone

methyl chloroformate

(3,4-diaminophenyl)phenylmethanone hydrochloride

dimethyl sulfoxide

Downstream raw materials:

(2-amino-1H-benzimidazol-5-yl)(phenyl)methanone

1-(5-benzoylbenzimidazol-2-yl)-3-(4-methylpiperazino)urea

1-(5-benzoylbenzimidazol-2-yl)-3-(2-hydroxyethyl)urea

1-(5-benzoylbenzimidazol-2-yl)-3-<2-<(2-hydroxyethyl)amino>ethyl>urea

Refernces

• 1、 Ke, Fang,Zhang, Peng,Lin, Chen,Lin, Xiaoyan,Xu, Jianhua,Zhou, Xiangge. "Synthesis of benzimidazoles by Cul-catalyzed three-component reaction of 2-haloaniline, ammonia and aldehyde in water". supporting information. p. 8090 - 8094. Retrieved 2018/11/23.
• 2、 Zhang, Jin,Fu, Lei-Lei,Tian, Mao,Liu, Hao-Qiu,Li, Jing-Jing,Li, Yan,He, Jun,Huang, Jian,Ouyang, Liang,Gao, Hui-Yuan,Wang, Jin-Hui. "Design and synthesis of a novel candidate compound NTI-007 targeting sodium taurocholate cotransporting polypeptide [NTCP]-APOA1-HBx-Beclin1-mediated autophagic pathway in HBV therapy". . p. 976 - 984. Retrieved 2015/03/04.