Taranabant

Taranabant (codenamed MK-0364) is a cannabinoid receptor type 1 (CB₁) inverse agonist that was investigated as a potential treatment for obesity due to its anorectic effects.^[1][2] It was developed by Merck & Co.

Taranabant

Clinical data
Routes of administration	Oral
ATC code	A08AX (WHO)
Legal status
Legal status	Investigational (failed)
Identifiers
IUPAC name N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyanophenyl)-2-butanyl]-2-methyl-2-{[5-(trifluoromethyl)-2-pyridinyl]oxy}propanamide
CAS Number	701977-09-5 Y
PubChem CID	11226090
ChemSpider	9401143
UNII	X9U622S114
CompTox Dashboard (EPA)	DTXSID60220464
ECHA InfoCard	100.207.983
Chemical and physical data
Formula	C27H25ClF3N3O2
Molar mass	515.96 g·mol−1
3D model (JSmol)	Interactive image
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 Key:QLYKJCMUNUWAGO-GAJHUEQPSA-N
(verify)

In October 2008, Merck stopped its phase III clinical trials with the drug due to high level of central nervous system side effects, mainly depression and anxiety.^[3][4][5][6]

See also

• Cannabinoid receptor antagonist