Details of the Drug

General Information of Drug (ID: DM5G9W0)

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

Disease Entry	ICD 11	Status	REF
Obesity	5B81	Discontinued in Phase 3	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

516

Logarithm of the Partition Coefficient (xlogp)

6.5

Rotatable Bond Count (rotbonds)

8

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

7

Chemical Identifiers

Formula: C27H25ClF3N3O2
IUPAC Name: N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyanophenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide
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

Cross-matching ID

PubChem CID: 11226090
CAS Number: 701977-09-5
UNII: X9U622S114
DrugBank ID: DB06624
TTD ID: D06TGE

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Cannabinoid receptor 1 (CB1)	TT6OEDT	CNR1_HUMAN	Antagonist	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Obesity

ICD Disease Classification

5B81

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Cannabinoid receptor 1 (CB1)	DTT	CNR1	5.59E-02	-0.22	-0.45
Cannabinoid receptor 1 (CB1)	DTT	CNR1	7.68E-01	-0.06	-0.46

Molecular Expression Atlas (MEA)

MEA Detail

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References

1	Obesity: pathophysiology and clinical management. Curr Med Chem. 2009;16(4):506-21.
2	Central side-effects of therapies based on CB1 cannabinoid receptor agonists and antagonists: focus on anxiety and depression. Best Pract Res Clin Endocrinol Metab. 2009 Feb;23(1):133-44.