210. Albendazole

Nomenclature

CAS number: 54965-21-8
[5-(Propylthio)-1H-benzimidazol-2-yl]carbamic acid methyl ester; methyl 5-(propylthio)-2-benzimidazolecarbamate; 5-(propylthio)-2-carbomethoxyaminobenzimidazole; SKF-62979; Albenza (GSK); Eskazole (GSK); Valbazen (Pfizer); Zentel (GSK).
C12H15N3O2S; mol wt 265.33.
C 54.32%, H 5.70%, N 15.84%, O 12.06%, S 12.08%.

Description and references

Prepn: R. J. Gyurik, V. J. Theodorides, US 3915986 (1975 to SmithKline). Anthelmintic spectrum: V. J. Theodorides, Experientia 32, 702 (1976) DOI PubMed. Metabolism: R. J. Gyurik et al., Drug Metab. Dispos. 9, 503 (1981) PubMed. Efficacy in cattle vs gastrointestinal parasites: J. C. Williams et al., Am. J. Vet. Res. 38, 2037 (1977) PubMed; vs liver flukes: T. M. Craig et al., ibid. 53, 1170 (1992) PubMed. Clinical trial in mixed helminth infections: P. Pene et al., Am. J. Trop. Med. Hyg. 31, 263 (1982) PubMed; in echinococcosis: R. J. Horton, Trans. R. Soc. Trop. Med. Hyg. 83, 97 (1989).

Chemical structure

Properties

Colorless crystals, mp 208-210°. Freely sol in anhydrous formic acid. Sol in DMSO, strong acids, strong bases. Slightly sol in methanol, chloroform, ethyl acetate, acetonitrile. Very slightly sol in ether, methylene chloride. Practically insol in water, alcohol.

Derivative

Sulfoxide.

Nomenclature

CAS number: 54029-12-8
Albendazole oxide; ricobendazole; rycobendazole; RS-8852; Rycoben (Novartis).
C12H15N3O3S; mol wt 281.33.
C 51.23%, H 5.37%, N 14.94%, O 17.06%, S 11.40%.

Description and references

Active metabolite of albendazole. Bioavailability: L. Dominguez et al., Farmaco 50, 697 (1995) PubMed.

Properties

mp 226-228° (dec).

Therapeutic Category

Anthelmintic (Cestodes).

Therapeutic Category (Veterinary)

Anthelmintic.

Keywords

Anthelmintic (Cestodes)