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

General Information of Drug (ID: DR3053)
Drug Name
Taranabant
Synonyms
Taranabant [USAN]; MK 0364; MK0364; MK-0364; MK-0634; Taranabant (INN/USAN); L]-2-methyl-2-[(5-(trifluoromethyl)pyridin-2-yl)oxy]propanamide; N-[(1S,2S)-3-(4-Chlorophenyl)-2-(3-cyanophenyl)-1-methylpropy; N-(3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl)-2-methyl-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)propanamide; N-[(1S,2S)-3-(4-Chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-[[5-(trifluoromethyl)pyridin-2-yl]oxy]propanamide; N-((1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl)-2-methyl-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)propanamide
Indication Obesity [ICD11: 5B80-5B81] Discontinued in Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 516 Topological Polar Surface Area 75
Heavy Atom Count 36 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
11226090
CAS Number
701977-09-5
TTD Drug ID
D06TGE
Formula
C27H25ClF3N3O2
Canonical SMILES
C[C@@H]([C@@H](CC1=CC=C(C=C1)Cl)C2=CC=CC(=C2)C#N)NC(=O)C(C)(C)OC3=NC=C(C=C3)C(F)(F)F
InChI
InChI=1S/C27H25ClF3N3O2/c1-17(34-25(35)26(2,3)36-24-12-9-21(16-33-24)27(29,30)31)23(14-18-7-10-22(28)11-8-18)20-6-4-5-19(13-20)15-32/h4-13,16-17,23H,14H2,1-3H3,(H,34,35)/t17-,23+/m0/s1
InChIKey
QLYKJCMUNUWAGO-GAJHUEQPSA-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
Taranabant Metabolite M1 DM018342 N. A. Oxidation - Monohydroxylation 1 [3]
Taranabant Metabolite M10 DM018346 N. A. Unclear - Unclear 1 [3]
Taranabant Metabolite M15 DM018345 N. A. Unclear - Unclear 1 [3]
Taranabant Metabolite M1a DM018348 N. A. Unclear - Unclear 1 [3]
Taranabant Metabolite M1b DM018347 N. A. Unclear - Unclear 1 [3]
Taranabant Metabolite M5 DM018344 N. A. Unclear - Unclear 1 [3]
Taranabant Metabolite M7 DM018343 N. A. Unclear - Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010328 Taranabant Taranabant Metabolite M1 Oxidation - Monohydroxylation Unclear [3]
MR010330 Taranabant Taranabant Metabolite M5 Unclear - Unclear Unclear [3]
MR010331 Taranabant Taranabant Metabolite M15 Unclear - Unclear Unclear [3]
MR010332 Taranabant Taranabant Metabolite M10 Unclear - Unclear Unclear [3]
MR010333 Taranabant Taranabant Metabolite M1b Unclear - Unclear Unclear [3]
MR010334 Taranabant Taranabant Metabolite M1a Unclear - Unclear Unclear [3]
MR010329 Taranabant Metabolite M1 Taranabant Metabolite M7 Unclear - Unclear Unclear [3]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Obesity: pathophysiology and clinical management. Curr Med Chem. 2009;16(4):506-21.
2 In vitro and in vivo metabolism of a novel cannabinoid-1 receptor inverse agonist, taranabant, in rats and monkeys
3 Metabolism and excretion of [14C]taranabant, a cannabinoid-1 inverse agonist, in humans

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