Details of the Drug

General Information of Drug (ID: DMPWGBR)

Drug Name

TRICLABENDAZOLE

Synonyms

Triclabendazole; 68786-66-3; Fasinex; 6-Chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzo[d]imidazole; C14H9Cl3N2OS; Triclabendazolum [INN-Latin]; Triclabendazol [INN-Spanish]; CCRIS 8988; UNII-4784C8E03O; CGA 89317; 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole; CPD000466357; MLS001424101; CHEMBL1086440; 6-Chloro-5-(2,3-dichlorophenoxy)-2-methylthio-benzimidazole; 4784C8E03O; NCGC00164610-01; Triclabendazole, 98%; SMR000466357; AK-68238; 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)benzimidazole

Indication

Disease Entry	ICD 11	Status	REF
Helminth infection	1F90.0	Approved	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

359.7

Logarithm of the Partition Coefficient (xlogp)

5.7

Rotatable Bond Count (rotbonds)

3

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

3

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 5.72 micromolh/L []
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 1.16 micromol/L []
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Elimination: In animals, triclabendazole is primarily excreted by the biliary tract in the feces (90%), together with the sulfoxide and sulfone metabolite []
Half-life: The concentration or amount of drug in body reduced by one-half in 8 hours (triclabendazole), 14 hours (the sulfoxide metabolites), and 11 hours (sulfone metabolites) []
Metabolism: The drug is metabolized via the CYP1A2 enzyme into its active sulfoxide metabolite and to a lesser extent by CYP2C9, CYP2C19, CYP2D6, CYP3A, and FMO (flavin containing monooxygenase) []
Vd: The volume of distribution (Vd) of drug is 1 L/kg []
Water Solubility: The ability of drug to dissolve in water is measured as 0.0002 mg/mL [2]

Chemical Identifiers

Formula: C14H9Cl3N2OS
IUPAC Name: 6-chloro-5-(2,3-dichlorophenoxy)-2-methylsulfanyl-1H-benzimidazole
Canonical SMILES: CSC1=NC2=CC(=C(C=C2N1)Cl)OC3=C(C(=CC=C3)Cl)Cl
InChI: 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)
InChIKey: NQPDXQQQCQDHHW-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 50248
ChEBI ID: CHEBI:94759
CAS Number: 68786-66-3
DrugBank ID: DB12245
TTD ID: D02VMJ
INTEDE ID: DR1639
ACDINA ID: D01502

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Trypanosoma Cruzipain (Trypano CYSP)	TTEAID7	CYSP_TRYCR	Inhibitor	[3]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[4]
Cytochrome P450 2D6 (CYP2D6)	DECB0K3	CP2D6_HUMAN	Substrate	[5]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[4]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[4]
Cytochrome P450 1A2 (CYP1A2)_{Main DME}	DEJGDUW	CP1A2_HUMAN	Substrate	[4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Potassium voltage-gated channel subfamily H member 2 (KCNH2)	OTZX881H	KCNH2_HUMAN	Gene/Protein Processing	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from TRICLABENDAZOLE (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Ivosidenib	DM8S6T7	Major	Increased risk of prolong QT interval by the combination of Triclabendazole and Ivosidenib.	Acute myeloid leukaemia [2A60]	[7]
Oliceridine	DM6MDCF	Moderate	Increased risk of prolong QT interval by the combination of Triclabendazole and Oliceridine.	Acute pain [MG31]	[8]
Levalbuterol	DM5YBO1	Moderate	Increased risk of prolong QT interval by the combination of Triclabendazole and Levalbuterol.	Asthma [CA23]	[9]
Selpercatinib	DMZR15V	Major	Increased risk of prolong QT interval by the combination of Triclabendazole and Selpercatinib.	Lung cancer [2C25]	[10]
Siponimod	DM2R86O	Major	Increased risk of ventricular arrhythmias by the combination of Triclabendazole and Siponimod.	Multiple sclerosis [8A40]	[11]
Ozanimod	DMT6AM2	Major	Increased risk of ventricular arrhythmias by the combination of Triclabendazole and Ozanimod.	Multiple sclerosis [8A40]	[12]
Rucaparib	DM9PVX8	Moderate	Increased risk of prolong QT interval by the combination of Triclabendazole and Rucaparib.	Ovarian cancer [2C73]	[13]
Macimorelin	DMQYJIR	Major	Increased risk of prolong QT interval by the combination of Triclabendazole and Macimorelin.	Pituitary gland disorder [5A60-5A61]	[14]
Lefamulin	DME6G97	Major	Increased risk of prolong QT interval by the combination of Triclabendazole and Lefamulin.	Pneumonia [CA40]	[7]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Haematite red	E00236	14833	Colorant
Hydrophobic colloidal silica	E00285	24261	Anticaking agent; Emulsion stabilizing agent; Glidant; Suspending agent; Viscosity-controlling agent
Methylhydroxyethylcellulose	E00703	Not Available	Coating agent; Emulsion stabilizing agent; Modified-release agent; Suspending agent; Binding agent; Viscosity-controlling agent
Pregelatinized starch	E00674	Not Available	Binding agent; Diluent; Disintegrant
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⏷ Show the Full List of 6 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Triclabendazole 250 mg tablet	250 mg	Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	BDDCS applied to over 900 drugs
3	Colloid formation by drugs in simulated intestinal fluid. J Med Chem. 2010 May 27;53(10):4259-65.
4	In vitro drug-drug interaction potential of sulfoxide and/or sulfone metabolites of albendazole, triclabendazole, aldicarb, methiocarb, montelukast and ziprasidone. Drug Metab Lett. 2018;12(2):101-116.
5	FDA Label of Egaten. The 2020 official website of the U.S. Food and Drug Administration.
6	Why are most phospholipidosis inducers also hERG blockers?. Arch Toxicol. 2017 Dec;91(12):3885-3895. doi: 10.1007/s00204-017-1995-9. Epub 2017 May 27.
7	Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
8	Iannini PB "Cardiotoxicity of macrolides, ketolides and fluoroquinolones that prolong the QTc interval." Expert Opin Drug Saf 1 (2002): 121-8. [PMID: 12904146]
9	Product Information. Arcapta Neohaler (indacaterol). Novartis Pharmaceuticals, East Hanover, NJ.
10	Product Information. Retevmo (selpercatinib). Lilly, Eli and Company, Indianapolis, IN.
11	Cerner Multum, Inc. "Australian Product Information.".
12	Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.
13	Canadian Pharmacists Association.
14	Product Information. Macrilen (macimorelin). Aeterna Zentaris, Charleston, SC.