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Details

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

SHOW SMILES / InChI
Structure of TRICLABENDAZOLE

SMILES

CSC1=NC2=CC(Cl)=C(OC3=C(Cl)C(Cl)=CC=C3)C=C2N1

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
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

Primary TargetPharmacologyConditionPotency
15.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Egaten
Curative
Egaten
Curative
Egaten

Cmax

ValueDoseCo-administeredAnalytePopulation
0.34 μM
10 mg/kg 1 times / day multiple, oral
TRICLABENDAZOLE plasma
Homo sapiens
1.16 μM
10 mg/kg 1 times / day multiple, oral
TRICLABENDAZOLE plasma
Homo sapiens
1.16 μM
10 mg/kg single, oral
TRICLABENDAZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1.55 μM × h
10 mg/kg 1 times / day multiple, oral
TRICLABENDAZOLE plasma
Homo sapiens
5.72 μM × h
10 mg/kg 1 times / day multiple, oral
TRICLABENDAZOLE plasma
Homo sapiens
5.72 μM × h
10 mg/kg single, oral
TRICLABENDAZOLE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8 h
10 mg/kg single, oral
TRICLABENDAZOLE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
3.3%
10 mg/kg single, oral
TRICLABENDAZOLE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

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
Record UNII
4784C8E03O
Record Status Validated (UNII)
Record Version