26097-80-3

Usage

Uses

Used in Pharmaceutical Industry:
Cambendazol is used as an antihelmintic agent for the treatment of strongyloidiasis in humans. It is effective in eradicating parasitic worms from the intestine and muscle tissues, providing relief from the symptoms and complications associated with the infection.
Used in Research and Development:
Cambendazol is used as a potential chemotherapeutic agent in the development of new treatments for parasitic infections. Its ability to inhibit microtubule polymerization makes it a valuable tool in studying the mechanisms of action and potential applications in combating various parasitic diseases.
Brand Name:
Cambendazol is marketed under the brand name Camdan by Merck, a leading pharmaceutical company. This brand name is associated with the quality and efficacy of the antihelmintic compound, ensuring patients receive a reliable and effective treatment option for strongyloidiasis.

InChI:InChI=1/C14H14N4O2S/c1-8(2)20-14(19)16-9-3-4-10-11(5-9)18-13(17-10)12-6-21-7-15-12/h3-8H,1-2H3,(H,16,19)(H,17,18)

Synthetic route

1,3-thiazole-4-carbaldehyde (3364-80-5) + 3,4-diaminophenylcarbamic acid isopropyl ester (35198-67-5) → cambendazol (26097-80-3)

Conditions	Yield
With sulfur In xylene for 8h; Heating;	1.1 g

2-nitro-1,4-phenylenediamine (5307-14-2) → cambendazol (26097-80-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 12 g / dimethylaniline / acetonitrile / 3 h / Ambient temperature 2: 6.5 g / H2, HCl / 10percent Pd-C / methanol; propan-2-ol / 760 Torr / Ambient temperature 3: 1.1 g / sulphur / xylene / 8 h / Heating View Scheme

4-isopropoxycarbonylamino-2-nitroaniline (30713-39-4) → cambendazol (26097-80-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 6.5 g / H2, HCl / 10percent Pd-C / methanol; propan-2-ol / 760 Torr / Ambient temperature 2: 1.1 g / sulphur / xylene / 8 h / Heating View Scheme

5-aminothiabendazole (25893-06-5) + isopropyl chloroformate (108-23-6) → cambendazol (26097-80-3)

Conditions	Yield
In pyridine; methanol; benzene

Upstream product

• 3364-80-5 1,3-thiazole-4-carbaldehyde 
• 35198-67-5 3,4-diaminophenylcarbamic acid isopropyl ester 
• 5307-14-2 2-nitro-1,4-phenylenediamine 
• 30713-39-4 4-isopropoxycarbonylamino-2-nitroaniline 
• 25893-06-5 5-aminothiabendazole 
• 108-23-6 isopropyl chloroformate 

Relevant academic research and scientific papers

Selective Functionalization of 2-Nitro-p-phenylenediamine : Part III - A New Route to 1-Arylbenzimidazole 5-carbamates, Including Cambendazole

Reaction of 3,4-diaminophenylcarbamic acid ethyl ester (2) with carboxymethyl dithiobenzoate (3) gives the thiobenzanilides (4a or 4b), which could be cyclized by acid to 2-phenylbenzimidazole-5-carbamic acid ethyl ester (5).The same product is obtained by the reaction of 2 with benzaldehyde and sulphur.Other aromatic aldehydes have been similarly reacted to give (9b-d).Cambendazole (9e) is obtained by the reaction of thiazole-4-aldehyde and sulphur with 3,4-diaminophenylcarbamic acid isopropyl ester (6e).

Compositions and methods for the treatment of helminthiasis

Compositions and methods for the treatment of helminthiasis are disclosed which utilize 5-isopropoxycarbonylamino-2-(4'-thiazolyl)-benzimidazole and 3'-chloro-4'-(p-chlorophenoxy)-3,5-diiodosalicylanilide as the active ingredients.