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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
[Antiparasitic treatments in pregnant women and in children in 2003].
2003
An ultrasensitive capture ELISA for detection of Fasciola hepatica coproantigens in sheep and cattle using a new monoclonal antibody (MM3).
2004 Aug
Response of two isolates of Fasciola hepatica to treatment with triclabendazole in vivo and in vitro.
2004 Dec
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
[Human infection with Dicrocoelium dendriticum].
2004 Nov 19
Triclabendazole biotransformation and comparative diffusion of the parent drug and its oxidized metabolites into Fasciola hepatica.
2004 Nov-Dec
Measurement of triclabendazole and its metabolites in liver flukes: method development and full validation.
2004 Sep 3
Fascioliasis imported to Norway.
2005
Monitoring and treatment of Fascioloides magna in semi-farm red deer husbandry in Croatia.
2005 Aug
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
Separation and characterization of synthetic impurities of triclabendazole by reversed-phase high-performance liquid chromatography/electrospray ionization mass spectrometry.
2005 Feb 7
Isolation, identification and expression of a Fasciola hepatica cDNA encoding a 2.9-kDa recombinant protein for the diagnosis of ovine fasciolosis.
2005 Jan
Fascioliasis in relatives of patients with Fasciola hepatica infection in Peru.
2005 Jul-Aug
[Four cases of hepatic fascioliasis mimicking cholangiocarcinoma].
2005 Jun
Lack of reversion in triclabendazole-resistant Fasciola hepatica.
2005 Mar 12
[Obstructive jaundice, Fasciola hepatica: a new case report].
2005 May-Aug
Infection with Fasciola hepatica.
2005 Nov
An outbreak of subacute fasciolosis in Soay sheep: ultrasonographic biochemical and histological studies.
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
Triclabendazole: new skills to unravel an old(ish) enigma.
2005 Sep
[Therapeutic alternatives in case of failure of first-line treatment of intestinal helminthiasis in adults].
2006 Aug
Triclabendazole and its two main metabolites lack activity against Schistosoma mansoni in the mouse model.
2006 Aug
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
Stage-specific differences in fecundity over the life-cycle of two characterized isolates of the liver fluke, Fasciola hepatica.
2006 Aug
Treatment of fascioliasis in human infections.
2006 Feb
Unusual thrombotic manifestations secondary to antiphospholipid syndrome and hepatic fascioliasis.
2006 Jan
Response from Savioli and colleagues from the Department of Neglected Tropical Diseases, World Health Organization.
2006 Jun
Assessment of the main metabolism pathways for the flukicidal compound triclabendazole in sheep.
2006 Jun
Fasciola hepatica infection: clinical and computerized tomographic findings of ten patients.
2006 Mar
[Hepatobiliary fasciolasis without eosinophilia].
2006 Oct
Fasciola hepatica: morphological effects of a combination of triclabendazole and clorsulon against mature fluke.
2006 Oct
Resistance of Fasciola hepatica to triclabendazole and albendazole in sheep in Spain.
2006 Sep 23
Activity of artemether and OZ78 against triclabendazole-resistant Fasciola hepatica.
2007 Dec
Human fascioliasis: a case of hyperinfection and an update for clinicians.
2007 Fall
The use of MM3 monoclonal antibodies for the early immunodiagnosis of ovine fascioliasis.
2007 Feb
Immature triclabendazole-resistant Fasciola hepatica: tegumental responses to in vitro treatment with the sulphoxide metabolite of the experimental fasciolicide compound alpha.
2007 Jan
[New drugs against parasitic diseases].
2007 Jan 31
Controlling fasciolosis in the Bolivian Altiplano.
2007 Jun
The effect of diet type on the plasma disposition of triclabendazole in goats.
2007 Jun
Food-borne trematodiasis: current chemotherapy and advances with artemisinins and synthetic trioxolanes.
2007 Nov
Obstructive jaundice with fever and eosinophilia.
2007 Nov
[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
A field trial of production and financial consequences of helminthosis control in sheep production in Ethiopia.
2008 Apr 17
Natural history, clinicoradiologic correlates, and response to triclabendazole in acute massive fascioliasis.
2008 Feb
Pharmacokinetic disposition of triclabendazole in cattle and sheep; discrimination of the order and the rate of the absorption process of its active metabolite triclabendazole sulfoxide.
2008 Jan
Use of triclabendazole for treatment of patients co-infected by Fasciola spp. and S. mansoni in Behera Governorate, Egypt.
2008 Mar
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