Triclabendazole

Triclabendazole
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	P02BX04 (WHO) QP52AC01 (WHO)
Pharmacokinetic data
Metabolism	Oxidation to the sulfone and sulfoxide parent compound
Biological half-life	22–24 hs
Excretion	Feces (>95%), urine (2%), milk (<1%)
Identifiers
IUPAC name 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole
CAS Number	68786-66-3^N
PubChem (CID)	50248
ChemSpider	45565^Y
UNII	4784C8E03O^Y
KEGG	D07364^N
ChEMBL	CHEMBL1086440^Y
ECHA InfoCard	100.127.414
Chemical and physical data
Formula	C₁₄H₉Cl₃N₂OS
Molar mass	359.658
3D model (Jmol)	Interactive image
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.^[1]

References

↑ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

Antiparasitics – Anthelmintics (P02) and Endectocides (QP54)

Antiplatyhelmintic agents

Antitrematodals
(schistosomicides)

Binds tubulin	benzimidazole Triclabendazole^#

AI	phosphonic acid Metrifonate^‡

Other/unknown	quinoline Praziquantel^# Oxamniquine^# phenol Bithionol thiazole Niridazole arylsulfonate Stibophen

Anticestodals
(taeniacides)

Binds tubulin	benzimidazole Albendazole^#

Other/unknown	quinoline Praziquantel^# salicylanilide Niclosamide^# aminoacridine Quinacrine butyrophenone Desaspidin chlorophenol Dichlorophen

Antinematodal agents
(including
macrofilaricides)

Binds tubulin	benzimidazole Mebendazole^# Albendazole^# Tiabendazole Fenbendazole Ciclobendazole Flubendazole

Glutamate-gated chloride channel, GABA receptor	avermectins Abamectin Doramectin Emamectin Ivermectin^# Selamectin milbemycins Moxidectin Milbemycin oxime

NMDA	tetrahydropyrimidine Pyrantel^# pyrantel pamoate Oxantel Morantel Carbantel Febantel (aka felsantel)

Other/unknown	piperazine Piperazine Diethylcarbamazine^# thiazole Levamisole^# quinolinium Pyrvinium benzylammonium Bephenium naphthalenesulfonate Suramin^# Tribendimidine

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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