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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

Molecular Formula C14H9Cl3N2OS
Molecular Weight 359.658
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Experimental infection of rabbits with Fasciola gigantica and treatment with triclabendazole (TCBZ) or BT6: parasitological, haematological and immunological findings.
2001
[Obstructive jaundice, Fasciola hepatica: a new case report].
2005 May-Aug
Resistance-induced changes in triclabendazole transport in Fasciola hepatica: ivermectin reversal effect.
2006 Dec
Seasonal differences in the incidence of infection with Fasciola gigantica in Cambodian cattle.
2006 Jan
Surgery in Fasciola hepatica pancreatitis: report of a case and review of literature.
2007 Apr
Understanding triclabendazole resistance.
2007 Apr
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
[New drugs against parasitic diseases].
2007 Jan 31
Controlling fasciolosis in the Bolivian Altiplano.
2007 Jun
Effect of Fascioliasis on the pharmacokinetic parameters of triclabendazole in human subjects.
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
Substance Class Chemical
Created
by admin
on Tue Mar 06 10:25:57 UTC 2018
Edited
by admin
on Tue Mar 06 10:25:57 UTC 2018
Record UNII
4784C8E03O
Record Status Validated (UNII)
Record Version
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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
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 Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
WHO-ATC P02BX04
Created by admin on Tue Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 6.1.3
Created by admin on Tue Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
Code System Code Type Description
CAS
68786-66-3
Created by admin on Tue Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
PRIMARY
EVMPD
SUB11267MIG
Created by admin on Tue Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
PRIMARY
NCI_THESAURUS
C75236
Created by admin on Tue Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
PRIMARY
MERCK INDEX
M11087
Created by admin on Tue Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
PRIMARY Merck Index
MESH
C039276
Created by admin on Tue Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
PRIMARY
EPA CompTox
68786-66-3
Created by admin on Tue Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
PRIMARY
ChEMBL
CHEMBL1086440
Created by admin on Tue Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
PRIMARY
PUBCHEM
50248
Created by admin on Tue Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
PRIMARY SWITZERF
INN
5003
Created by admin on Tue Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
PRIMARY
WIKIPEDIA
TRICLABENDAZOLE
Created by admin on Tue Mar 06 10:25:57 UTC 2018 , Edited by admin on Tue Mar 06 10:25:57 UTC 2018
PRIMARY
Related Record Type Details
ACTIVE MOIETY