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
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)
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
PubMed
Title | Date | PubMed |
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[Obstructive jaundice, Fasciola hepatica: a new case report]. | 2005 May-Aug |
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Activity of artemether and OZ78 against triclabendazole-resistant Fasciola hepatica. | 2007 Dec |
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Human fascioliasis: a case of hyperinfection and an update for clinicians. | 2007 Fall |
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[New drugs against parasitic diseases]. | 2007 Jan 31 |
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Food-borne trematodiasis: current chemotherapy and advances with artemisinins and synthetic trioxolanes. | 2007 Nov |
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Obstructive jaundice with fever and eosinophilia. | 2007 Nov |
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[Fascioliasis: a 23-year retrospective study]. | 2007 Nov |
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Fasciola hepatica: the infectivity of cattle-origin miracidia had increased over the past years in central France. | 2007 Sep |
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A field trial of production and financial consequences of helminthosis control in sheep production in Ethiopia. | 2008 Apr 17 |
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Natural history, clinicoradiologic correlates, and response to triclabendazole in acute massive fascioliasis. | 2008 Feb |
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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
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
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Classification Tree | Code System | Code | ||
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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
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WHO-ATC |
P02BX04
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FDA ORPHAN DRUG |
564216
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admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
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WHO-ESSENTIAL MEDICINES LIST |
6.1.3
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admin on Tue Oct 22 00:08:02 UTC 2019 , Edited by admin on Tue Oct 22 00:08:02 UTC 2019
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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
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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
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68786-66-3
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SUB11267MIG
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C75236
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M11087
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C039276
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68786-66-3
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CHEMBL1086440
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50248
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5003
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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
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PRIMARY |
ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
METABOLITE ACTIVE (PARENT)