Thiabendazole

Base Information

• Chemical Name: Thiabendazole
• CAS No.: 148-79-8
• Deprecated CAS: 123242-33-1,145316-67-2,8018-04-0,8027-10-9,8028-27-1,94977-06-7,98002-42-7,1135441-27-8,1135441-27-8,145316-67-2,8018-04-0,8027-10-9,94977-06-7,98002-42-7
• Molecular Formula: C10H7N3S
• Molecular Weight: 201.252
• Hs Code.: 2934.10
• European Community (EC) Number: 205-725-8
• NSC Number: 757347,525040,90507
• UN Number: 3077,2588
• UNII: N1Q45E87DT
• DSSTox Substance ID: DTXSID0021337
• Nikkaji Number: J2.961K
• Wikipedia: Tiabendazole
• Wikidata: Q424986
• NCI Thesaurus Code: C873
• Pharos Ligand ID: MCV61RRRWNWZ
• Metabolomics Workbench ID: 43036
• ChEMBL ID: CHEMBL625
• Mol file: 148-79-8.mol

Synonyms:2-(4'-Thiazolyl)Benzimidazole;Mintesol;Mintezol;Omnizole;Thiabendazole;Thibendole;Tiabendazol

Chemical Property of Thiabendazole

Chemical Property:

• Appearance/Colour: light yellow powder
• Vapor Pressure: 3.89E-06mmHg at 25°C
• Melting Point: 298-301 °C
• Refractive Index: 1.731
• Boiling Point: 446 °C at 760 mmHg
• PKA: pKa 4.7 (Uncertain)
• Flash Point: 226.2 °C
• PSA: 69.81000
• Density: 1.406 g/cm³
• LogP: 2.68640
• Storage Temp.: 0-6°C
• Solubility.: Soluble in methanol and dimethyl sulfoxide.
• Water Solubility.: 0.005 g/100 mL
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 201.03606841
• Heavy Atom Count: 14
• Complexity: 212
• Transport DOT Label: Class 9

Purity/Quality:

≥99% ^*data from raw suppliers

Thiabendazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: N,Xi
• Statements: 50/53-36/37/38
• Safety Statements: 60-61-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Animal Feed Additives
• Drug Classes: Anthelmintic Agents
• Canonical SMILES: C1=CC=C2C(=C1)NC(=N2)C3=CSC=N3
• Recent EU Clinical Trials: Randomized study on therapy of Strongyloides stercoralis invasion: ivermectine VS thiabendazole
• Physical properties: MW 201, pKa not known. Practically insoluble in water.
• Indications: Thiabendazole is primarily indicated in infections with Strongyloides stercoralis and cutaneous larva migrans. It may also prove useful against Capillaria philippinensis, Trichostrongylus species and alleviate symptoms during the invasion stage of trichinosis.
• Description: Thiabendazole is a kind of fungicide and parasiticide. As a fungicide, it can be used for the treatment of mold, blight and many other fungal diseases occurring in fruits and vegetable. As an antiparasitic, it is capable of treating roundworms, hookworms, and other kinds of helminth species that can attack wild animals, livestock and humans. It also has effects of inhibiting the angiogenesis of cells. The mechanism of action is still not fully understood. It has found that Thiabendazole is capable of suppressing the helminth-specific mitochondrial enzyme fumarate reductase, further inhibiting the citric acid cycle, mitochondrial respiration and ATP production, leading to helminth’s death. It may also inhibit the microtubule polymerization processes. Thiabendazole is a broad-spectrum anthelmintic that is active against a variety of helminths. In sheep, thiabendazole (50 mg/kg) kills greater than 95% of adult worms from ten genera, including Trichostrongylus, Cooperia, Nematodirus, Ostertagia, Haemonchus, Oesophagostomum, Bunostomum, Strongyloides, Chabertia, and Trichuris. It also inhibits production of eggs and disrupts larval development. Thiabendazole inhibits fumarate reductase in helminths, which inhibits succinate formation, and therefore energy production through the citric acid cycle. It also inhibits methionine aminopeptidase in E. coli (Ki = 40 nM; IC50 = 47.2 nM). Formulations containing thiabendazole have been used in the control of parasitic infections in livestock. Thiabendazole is also a broad-spectrum systemic fungicide against many fungal pathogens, although this compound was originally introduced as an anthelminthic (25).
• Uses: A drug used in the treatment of helminthiases anticoagulant, rodenticide Thiabendazole is widely used as a post-harvest systemic fungicide on citrus and bananas. It is active against fruit rots in bananas, citrus, apples and pears; bulb and corm rots in ornamentals; storage rots in sweet potato and potato and is also used to control Dutch elm disease. It is the original benzimidazole anthelmintic for both human and animal health usages. Systemic fungicide used for diseases of fruits and vegetables and for control of Dutch elm disease.
• Therapeutic Function: Anthelmintic
• Clinical Use: 2-(4-Thiazolyl)benzimidazole (Mintezol) occurs as a whitecrystalline substance that is only slightly soluble in waterbut is soluble in strong mineral acids. Thiabendazole is abasic compound with a pKa of 4.7 that forms complexeswith metal ions.Thiabendazole inhibits the helminth-specific enzymefumarate reductase. It is not known whether metal ionsare involved or if the inhibition of the enzyme is related tothiabendazole’s anthelmintic effect. Benzimidazole anthelminticdrugs such as thiabendazole and mebendazolealso arrest nematode cell division in metaphase by interferingwith microtubule assembly. They exhibit a highaffinity for tubulin, the precursor protein for microtubulesynthesis.Thiabendazole has broad-spectrum anthelmintic activity.It is used to treat enterobiasis, strongyloidiasis (threadworminfection), ascariasis, uncinariasis (hookworm infection), andtrichuriasis (whipworm infection). It has also been used torelieve symptoms associated with cutaneous larva migrans(creeping eruption) and the invasive phase of trichinosis. Inaddition to its use in human medicine, thiabendazole iswidely used in veterinary practice to control intestinalhelminths in livestock.

Technology Process of Thiabendazole

There total 22 articles about Thiabendazole 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: 97.82%

C10H9N3S*ClH → thiabendazole (148-79-8,98002-42-7)

Guidance literature:

With sodium hypochlorite; sodium carbonate; In methanol; water; at 0 - 65 ℃; for 1.5h; pH=9 - 10;

Reference yield: 92.7%

thiazole-4-carbonitrile (1452-15-9) + 1,2-diamino-benzene (95-54-5) + ascorbic acid (50-81-7,98966-42-8) → thiabendazole (148-79-8,98002-42-7)

Guidance literature:

With hydrogenchloride; ethylenediaminetetraacetic acid; In water;

Reference yield: 91.7%

thiazole-4-carbonitrile (1452-15-9) + o-phenylenediamine hydrochloride (39145-59-0) + 1,2-diamino-benzene (95-54-5) + ascorbic acid (50-81-7,98966-42-8) → thiabendazole (148-79-8,98002-42-7)

Guidance literature:

With hydrogenchloride; ethylenediaminetetraacetic acid; In methanol; water;

upstream raw materials:

thiazole-4-carbonitrile

aminosulfonic acid

1,2-diamino-benzene

ascorbic acid

Downstream raw materials:

4-(1-methyl-1H-benzo[d]imidazol-2-yl)thiazole

5-Hydroxythiabendazole

xanthene

C₁₈H₁₂Cl₂N₄OS

Refernces

• 1、 Zhang, Chao,Zhong, Bo,Yang, Simin,Pan, Liangkun,Yu, Siwang,Li, Zhongjun,Li, Shuchun,Su, Bin,Meng, Xiangbao. "Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents". . p. 3774 - 3780. Retrieved 2015.
• 2、 Silky, Sethy,Mandal, Sudip Kumar,Ewies, Ewies Fawzy,Neerupma, Dhiman,Arun, Garg. "Synthesis, characterization and biological evaluation of benzimidazole and benzindazole derivatives as anti-hypertensive agents". . p. 3659 - 3664. Retrieved 2021/07/10.
• 3、 -. "Preparation method of thiabendazole technical". . . Retrieved 2019/08/03.