Albendazole

Title: Albendazole
CAS Registry Number: 54965-21-8
CAS Name: [5-(Propylthio)-1H-benzimidazol-2-yl]carbamic acid methyl ester
Additional Names: methyl 5-(propylthio)-2-benzimidazolecarbamate; 5-(propylthio)-2-carbomethoxyaminobenzimidazole
Manufacturers' Codes: SKF-62979
Trademarks: Albenza (GSK); Eskazole (GSK); Valbazen (Pfizer); Zentel (GSK)
Molecular Formula: C12H15N3O2S
Molecular Weight: 265.33
Percent Composition: C 54.32%, H 5.70%, N 15.84%, O 12.06%, S 12.08%
Literature References: Prepn: R. J. Gyurik, V. J. Theodorides, US 3915986 (1975 to SmithKline). Anthelmintic spectrum: V. J. Theodorides, Experientia 32, 702 (1976). Metabolism: R. J. Gyurik et al., Drug Metab. Dispos. 9, 503 (1981). Efficacy in cattle vs gastrointestinal parasites: J. C. Williams et al., Am. J. Vet. Res. 38, 2037 (1977); vs liver flukes: T. M. Craig et al., ibid. 53, 1170 (1992). Clinical trial in mixed helminth infections: P. Pene et al., Am. J. Trop. Med. Hyg. 31, 263 (1982); in echinococcosis: R. J. Horton, Trans. R. Soc. Trop. Med. Hyg. 83, 97 (1989).
Properties: Colorless crystals, mp 208-210°. Sol in DMSO, strong acids, strong bases; slightly sol in methanol, chloroform, ethyl acetate, acetonitrile. Practically insol in water.
Melting point: mp 208-210°
Derivative Type: Sulfoxide
CAS Registry Number: 54029-12-8
Additional Names: Albendazole oxide; ricobendazole; rycobendazole
Manufacturers' Codes: RS-8852
Trademarks: Rycoben (Novartis)
Molecular Formula: C12H15N3O3S
Molecular Weight: 281.33
Percent Composition: C 51.23%, H 5.37%, N 14.94%, O 17.06%, S 11.40%
Literature References: Active metabolite of albendazole. Bioavailability: L. Dominguez et al., Farmaco 50, 697 (1995).
Properties: mp 226-228° (dec).
Melting point: mp 226-228° (dec)
Therap-Cat: Anthelmintic (Cestodes).
Therap-Cat-Vet: Anthelmintic.
Keywords: Anthelmintic (Cestodes).
Albizziin Albofungin Albomycin Alborixin Albuterol

Albendazole
Albendazole2DACS.svg
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Systematic (IUPAC) name
Methyl [5-(propylthio)-1H-benzoimidazol-2-yl]carbamate
Clinical data
Trade names Albenza
AHFS/Drugs.com monograph
MedlinePlus a610019
Pregnancy cat. D (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability <5%[1]
Protein binding 70%[1]
Metabolism Hepatic[1]
Half-life 8-12 hours[1]
Excretion Urine, faeces[1]
Identifiers
CAS number 54965-21-8 YesY
ATC code P02CA03 QP52AC11
PubChem CID 2082
DrugBank DB00518
ChemSpider 1998 YesY
UNII F4216019LN YesY
KEGG D00134 YesY
ChEBI CHEBI:16664 YesY
ChEMBL CHEMBL1483 YesY
NIAID ChemDB 007895
Chemical data
Formula C12H15N3O2S 
Mol. mass 265.333 g/mol
 YesY (what is this?)  (verify)

Albendazole, marketed as Albenza (United States), Eskazole, Zentel, Andazol and Alworm, is a benzimidazole drug used for the treatment of a variety of parasitic worm infestations. Although its use is widespread in the United States, the U.S. Food and Drug Administration (FDA) has not approved albendazole for this indication. It is marketed by Amedra Pharmaceuticals. Albendazole was first discovered at the SmithKline Animal Health Laboratories in 1972. It is a broad spectrum anthelmintic, effective against roundworms, tapeworms, and flukes of domestic animals and humans.[2]

Albendazole is a WHO Essential Medicine.