Albendazole

Albendazole

File:Albendazole.svg
Clinical data
Pregnancy category	D
Routes of administration	only oral route
ATC code	P02CA03 (WHO)
Legal status
Legal status	on the counter (OTC)
Pharmacokinetic data
Metabolism	oxidation of sulphur atom to sulphoxide, the active metabolite
Identifiers
IUPAC name methyl [(5-propylsulfanyl-3H- benzoimidazol-2-yl) amino]formate
CAS Number	54965-21-8
PubChem CID	2082
DrugBank	APRD00782
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C12H15N3O2S
Molar mass	265.333 g/mol

Albendazole, marketed as Albenza, Eskazole or Zentel, is a member of the benzimidazole compounds used as a drug indicated for the treatment of a variety of worm infestations. Although this use is widespread in the United States, the FDA has not approved albendazole for this indication.

Uses

It is effective against

• threadworms or pinworms
• roundworms,
• whipworms
• tapeworms
• hookworms

Mode of action

Vermicidal: Albendazole (C₁₂H₁₅N₃O₂S) causes degenerative alterations in the tegument and intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. The loss of the cytoplasmic microtubules leads to impaired uptake of glucose by the larval and adult stages of the susceptible parasites, and depletes their glycogen stores. Degenerative changes in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP), which is the energy required for the survival of the helminth. Due to diminished energy production, the parasite is immobilized and eventually dies.

Albendazole also has been shown to inhibit the enzyme fumarate reductase, which is helminth-specific. This action may be considered secondary to the effect on the microtubules due to the decreased absorption of glucose. This action occurs in the presence of reduced amounts of nicotinamide-adenine dinucleotide in reduced form (NADH), which is a coenzyme involved in many cellular oxidation-reduction reactions.

Albendazole has larvicidal effects in necatoriasis and ovicidal effects in ascariasis, ancylostomiasis, and trichuriasis.

Pregnancy class

D (Australia) - Do not take when pregnant, and do not become pregnant for one month after taking this drug.

See also

• Mebendazole

Template:Anthelmintics