Albendazole

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Contents

Albendazole (Albenza, Eskazole, Zentel)

Effective Against

Lymphatic Filariasis

Albendazole works as a vermicidal by keeping the worm from absorbing sugar (glucose), so that the worm loses energy and dies.



Cost

To consumers: 29 USD for 30 200mg pills from http://www.aclepsa.com

From Sigma-Aldrich: 49.80 USD (10g)

Reported Routes of Synthesis:

Image:129625-01-a.jpg

The condensation of 3-chloro-6-nitroacetanilide (I) with propylmercaptane (A) by means of aqueous refluxing NaOH gives 2-nitro-5-propylthioaniline (II), which was reduced with H2 over Pd/C in ethanol HCl to yield 4-propylthio-o-phenylenediamine (III). The cyclization of (III) with cyanogen bromide affords 2-amino-5-propylthiobenzimidazole (IV), which is finally condensed with methyl chloroformate. It can be condensed directly with a mixture of cyanamide and methyl chloroformate or with carbomethoxycyanamide (B). All these condensations are performed in basic medium.

Castaner, J.; Bogan, J. Albendazole. Drugs Fut 1977, 2(2): 81

Gyurik, RJ; Theodorides, VJ; Methyl 5-propylthio-2-benzimidazolecarbamate. DE 2527065; FR 2275203; GB 1464326; JP 51012936; US 3915986

Cost of Starting Materials and Selected Reagents:
Starting material 3-chloro-6-nitroacetanilide pricing not available from Sigma-Aldrich
Propylmercaptane (1-Propanethiol) from Sigma-Aldrich: 32.7 USD (250 mL)
Cyanogen bromide from Sigma-Aldrich: 114.5 USD (25 g)
Methyl chloroformate from Sigma-Aldrich: 137.5 USD (1 L)
Cyanamide from Sigma-Aldrich: 17.2 USD (5 g)
Carbomethoxycyanamide pricing not available from Sigma-Aldrich

Submitted Syntheses