Triclabendazole

Triclabendazole

Systematic (IUPAC) name
5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	?
Legal status	?
Routes of administration	?
Pharmacokinetic data
Metabolism	oxidation to the sulfone and sulfoxide parent compound
Biological half-life	22 - 24 hs
Excretion	>95% in faeces, 2% in urine, and < 1% in milk
Identifiers
CAS Number	68786-66-3 N
ATC code	P02BX04 (WHO) QP52AC01 (WHO)
PubChem	CID: 50248
ChemSpider	45565 Y
UNII	4784C8E03O Y
ChEMBL	CHEMBL1086440 Y
Chemical data
Formula	C14H9Cl3N2OS
Molecular mass	359.658
SMILES Clc3cccc(Oc2c(Cl)cc1c(nc(SC)n1)c2)c3Cl
InChI InChI=1S/C14H9Cl3N2OS/c1-21-14-18-9-5-8(16)12(6-10(9)19-14)20-11-4-2-3-7(15)13(11)17/h2-6H,1H3,(H,18,19) Y Key:NQPDXQQQCQDHHW-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Triclabendazole (commercial names: veterinary, liquid: Fasinex; human, tablets: Egaten, both manufactured by Novartis) is a member of the benzimidazole family of anthelmintics. The benzimidazole drugs share a common molecular structure, triclabendazole being the exception in having a chlorinated benzene ring but no carbamate group. Benzimidazoles such as triclabendazole are generally accepted to bind to beta-tubulin and prevent the polymerization of the microtubules of which they are part.

Triclabendazole was initially only developed as an oral route drug, and displays high efficacy against both immature and adult liver flukes.

Since late 1990s, triclabendazole became available as a generic drug, as patents expired in many countries. Many products were developed then. Among them, Trivantel 15, a 15% triclabendazole suspension, was launched by Agrovet Market Animal Health in the early 2000s. In 2009, the first triclabendazole injectable solution (combined with ivermectin) was developed and launched, also by Agrovet Market Animal Health. The product, Fasiject Plus, a triclabendazole 36% and ivermectin 0.6% solution, is designed to treat infections by Fasciola hepatica (both immature and adult liver flukes), roundworms and ectoparasites, as well.

It is on the World Health Organization's List of Essential Medicines, the most important medication needed in a basic health system.