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Details

Stereochemistry ACHIRAL
Molecular Formula C14H9Cl3N2OS
Molecular Weight 359.658
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRICLABENDAZOLE

SMILES

CSC1=NC2=C(N1)C=C(OC3=CC=CC(Cl)=C3Cl)C(Cl)=C2

InChI

InChIKey=NQPDXQQQCQDHHW-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description

Triclabendazole, (brand name Avomec, Egaten, etc) is a member of the benzimidazole family of anthelmintics used to treat liver flukes, specifically fascioliasis and paragonimiasis. Triclabendazole used routinely since 1983 in veterinary practice for the treatment of fascioliasis. It was not used in humans until the 1989 epidemic of fascioliasis near the Caspian Sea when Iranian authorities approved the use of the veterinary formulation to treat the infection. Fasciolicidal not only against the adult worms present in the biliary ducts, but also against the immature larval stages of Fasciola migrating through the hepatic parenchyma. Triclabendazole is shown to penetrate into liver flukes by transtegumentary absorption followed by inhibition of the parasite's motility, probably related to the destruction of the microtubular structure, resulting in the death of the parasite; the immobilizing effect is paralleled by changes in the parasite's resting tegumental membrane potential, strongly inhibiting the release of proteolytic enzymes, a process that appears critical to the survival of the parasite. Side effects are generally few, but can include abdominal pain and headaches. Biliary colic may occur due to dying worms. While no harms have been found with use during pregnancy, triclabendazole has not been well studied in this population. Triclabendazole is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is not commercially available in the United States.

Originator

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Egaten
Primary
Egaten
Primary
Egaten
PubMed

PubMed

TitleDatePubMed
Effect of fasciolicides on the antigenaemia in sheep naturally infected with Fasciola hepatica.
2001 Aug
Efficacy of combined chemotherapy against gastrointestinal nematodes and Fasciola hepatica in cattle.
2001 Aug 20
Characterisation of a beta-tubulin gene from the liver fluke, Fasciola hepatica.
2001 Sep
A comparative study on the effect of praziquantel and triclabendazole on Vampirolepis nana in vitro.
2002 Apr
Fasciola gigantica: tegumental surface alterations following treatment in vitro with the sulphoxide metabolite of triclabendazole.
2002 Apr
A praziquantel-ineffective fascioliasis case successfully treated with triclabendazole.
2002 Jun
The efficacy of formulations of triclabendazole and ivermectin in combination against liver fluke (Fasciola hepatica) and gastro-intestinal nematodes in cattle and sheep and sucking lice species in cattle.
2002 Nov
Development and validation of a liquid chromatographic-electrospray tandem mass spectrometric multiresidue method for anthelmintics in milk.
2002 Nov 8
[Antiparasitic treatments in pregnant women and in children in 2003].
2003
Fasciola hepatica infestation with joint symptoms.
2003 Feb
Pre-exposure of cattle to drug-abbreviated Fasciola hepatica infections: the effect upon subsequent challenge infection and the early immune response.
2003 Jan 20
Comparison of two single-day regimens of triclabendazole for the treatment of human pulmonary paragonimiasis.
2003 Jul-Aug
The effect of metronidazole in treating human fascioliasis.
2003 Oct
The effect of the microtubule inhibitor tubulozole-C on the tegument of triclabendazole-susceptible and triclabendazole-resistant Fasciola hepatica.
2003 Sep
Comparative assessment of the access of albendazole, fenbendazole and triclabendazole to Fasciola hepatica: effect of bile in the incubation medium.
2004 Jan
Randomized trial of a single, double and triple dose of 10 mg/kg of a human formulation of triclabendazole in patients with fascioliasis.
2004 Nov
Triclabendazole biotransformation and comparative diffusion of the parent drug and its oxidized metabolites into Fasciola hepatica.
2004 Nov-Dec
Control of human fascioliasis by selective chemotherapy: design, cost and effect of the first public health, school-based intervention implemented in endemic areas of the Nile Delta, Egypt.
2005 Aug
Triclabendazole for the treatment of fascioliasis and paragonimiasis.
2005 Dec
Fascioliasis in relatives of patients with Fasciola hepatica infection in Peru.
2005 Jul-Aug
[Four cases of hepatic fascioliasis mimicking cholangiocarcinoma].
2005 Jun
[Obstructive jaundice, Fasciola hepatica: a new case report].
2005 May-Aug
Infection with Fasciola hepatica.
2005 Nov
Eurytrema pancreaticum: the in vitro effect of praziquantel and triclabendazole on the adult fluke.
2005 Nov
Altered drug influx/efflux and enhanced metabolic activity in triclabendazole-resistant liver flukes.
2005 Oct
[Design of a Russian sample of the antifascioliasis antihelminthic triclabendazole and evaluation of its therapeutic efficiency].
2005 Oct-Dec
Adult triclabendazole-resistant Fasciola hepatica: surface and subsurface tegumental responses to in vitro treatment with the sulphoxide metabolite of the experimental fasciolicide compound alpha.
2006 Aug
Treatment of fascioliasis in human infections.
2006 Feb
Seasonal differences in the incidence of infection with Fasciola gigantica in Cambodian cattle.
2006 Jan
Response from Savioli and colleagues from the Department of Neglected Tropical Diseases, World Health Organization.
2006 Jun
Fasciola hepatica infection: clinical and computerized tomographic findings of ten patients.
2006 Mar
Understanding triclabendazole resistance.
2007 Apr
Fasciola hepatica: ultrastructural effects of a combination of triclabendazole and clorsulon against mature fluke.
2007 Apr
Activity of artemether and OZ78 against triclabendazole-resistant Fasciola hepatica.
2007 Dec
Immature triclabendazole-resistant Fasciola hepatica: tegumental responses to in vitro treatment with the sulphoxide metabolite of the experimental fasciolicide compound alpha.
2007 Jan
Controlling fasciolosis in the Bolivian Altiplano.
2007 Jun
An in vitro effect of propolis on adult worms of Fasciola gigantica.
2007 Mar 31
[Fascioliasis: a 23-year retrospective study].
2007 Nov
Fasciola hepatica: the infectivity of cattle-origin miracidia had increased over the past years in central France.
2007 Sep
Natural history, clinicoradiologic correlates, and response to triclabendazole in acute massive fascioliasis.
2008 Feb
Patents

Sample Use Guides

In Vivo Use Guide
10 mg per kg of body weight as a single dose
Route of Administration: Oral
In Vitro Use Guide
Triclabendazole was tested in vitro against recently excysted metacercariae. Triclabendazole was evaluated at concentrations of 10 and 50 mg/L., Triclabendazole demonstrated a fasciolicidal efficacy of 100% at a concentration of 10 and 50 mg/L at 24, 48 h and 72 hours post-treatment
Name Type Language
TRICLABENDAZOLE
INN   MART.   MI  
USAN   INN  
Official Name English
1H-BENZIMIDAZOLE, 6-CHLORO-5-(2,3-DICHLOROPHENOXY)-2-(METHYLTHIO)-
Systematic Name English
NVP-EGA230
Code English
TRICLABENDAZOLE [MART.]
Common Name English
EGATEN
Brand Name English
TRICLABENDAZOLE [INN]
Common Name English
EGA230B
Code English
TRICLABENDAZOLE [MI]
Common Name English
5-CHLORO-6-(2,3-DICHLOROPHENOXY)-2-(METHYLTHIO)-1H-BENZIMIDAZOLE
Systematic Name English
TRICLABENDAZOLE [WHO-DD]
Common Name English
FASINEX
Brand Name English
TRICLABENDAZOLE [USAN]
Common Name English
Classification Tree Code System Code
WHO-VATC QP52AC01
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
WHO-ATC P02BX04
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
FDA ORPHAN DRUG 564216
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.1.3
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
NCI_THESAURUS C250
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
FDA ORPHAN DRUG 525416
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
Code System Code Type Description
CAS
68786-66-3
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
PRIMARY
EVMPD
SUB11267MIG
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
PRIMARY
NCI_THESAURUS
C75236
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
PRIMARY
MERCK INDEX
M11087
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
PRIMARY Merck Index
MESH
C039276
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
PRIMARY
EPA CompTox
68786-66-3
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
PRIMARY
ChEMBL
CHEMBL1086440
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
PRIMARY
PUBCHEM
50248
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
PRIMARY
INN
5003
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
PRIMARY
WIKIPEDIA
TRICLABENDAZOLE
Created by admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
PRIMARY