Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1639)
Drug Name
Triclabendazole
Synonyms
Triclabendazol [INN-Spanish]; Triclabendazole; Triclabendazole, 98%; Triclabendazolum [INN-Latin]; Fasinex; 4784C8E03O; 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole; 6-Chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzo[d]imidazole; 6-Chloro-5-(2,3-dichlorophenoxy)-2-methylthio-benzimidazole; 68786-66-3; AK-68238; C14H9Cl3N2OS; CCRIS 8988; CGA 89317; CGA-89317; CHEMBL1086440; CPD000466357; MLS001424101; NCGC00164610-01; SMR000466357; UNII-4784C8E03O
Indication Fascioliasis [ICD11: 1F82] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 359.7 Topological Polar Surface Area 63.2
Heavy Atom Count 21 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
50248
ChEBI ID
CHEBI:94759
CAS Number
68786-66-3
TTD Drug ID
D02VMJ
Formula
C14H9Cl3N2OS
Canonical SMILES
CSC1=NC2=CC(=C(C=C2N1)Cl)OC3=C(C(=CC=C3)Cl)Cl
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
keto-triclabendazole DM019938
97182216
Unclear 1 [4]
TCBZ-SX DM002389
127657
Oxidation - Oxidation 1 [4] , [5]
Triclabendazole sulfone metabolite DM002390
10340439
Oxidation - Oxidation 2 [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002908 Triclabendazole TCBZ-SX Oxidation - Oxidation CYP1A2 [4], [5]
MR002910 Triclabendazole keto-triclabendazole Unclear Unclear [4]
MR002909 TCBZ-SX Triclabendazole sulfone metabolite Oxidation - Oxidation CYP2C19 ... [4], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Triclabendazole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 FDA Label of Egaten. The 2020 official website of the U.S. Food and Drug Administration.
4 Total determination of triclabendazole and its metabolites in bovine tissues using liquid chromatography-tandem mass spectrometry J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Mar 1;1109:54-59. doi: 10.1016/j.jchromb.2019.01.021.
5 Egaten FDA label

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