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.

Routes of
administrationOral

ATC code

A08AX (WHO)

Legal status

Investigational (failed)

CAS Number

701977-09-5^Y

Quick facts Clinical data, Routes ofadministration ...

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]

References

[1]
Armstrong HE, Galka A, Lin LS, Lanza TJ Jr, Jewell JP, Shah SK, et al. (2007). "Substituted acyclic sulfonamides as human cannabinoid-1 receptor inverse agonists". Bioorganic & Medicinal Chemistry Letters. 17 (8): 2184–7. doi:10.1016/j.bmcl.2007.01.087. PMID 17293109.
[2]
Fong TM, Guan XM, Marsh DJ, Shen CP, Stribling DS, Rosko KM, et al. (Jun 2007). "Antiobesity efficacy of a novel cannabinoid-1 receptor inverse agonist, N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-5-(trifluoromethyl)pyridin-2-yl]oxy]propanamide (MK-0364), in rodents". Journal of Pharmacology and Experimental Therapeutics. 321 (3): 1013–22. doi:10.1124/jpet.106.118737. PMID 17327489. S2CID 20001781.
[3]
"Press release by Merck". Retrieved 4 October 2008.
[4]
Aronne LJ, Tonstad S, Moreno M, Gantz I, Erondu N, Suryawanshi S, Molony C, Sieberts S, Nayee J, Meehan AG, Shapiro D, Heymsfield SB, Kaufman KD, Amatruda JM (May 2010). "A clinical trial assessing the safety and efficacy of taranabant, a CB1R inverse agonist, in obese and overweight patients: a high-dose study". International Journal of Obesity. 34 (5): 919–35. doi:10.1038/ijo.2010.21. PMID 20157323. S2CID 6769554.
[5]
Kipnes MS, Hollander P, Fujioka K, Gantz I, Seck T, Erondu N, Shentu Y, Lu K, Suryawanshi S, Chou M, Johnson-Levonas AO, Heymsfield SB, Shapiro D, Kaufman KD, Amatruda JM (June 2010). "A one-year study to assess the safety and efficacy of the CB1R inverse agonist taranabant in overweight and obese patients with type 2 diabetes". Diabetes, Obesity & Metabolism. 12 (6): 517–31. doi:10.1111/j.1463-1326.2009.01188.x. PMID 20518807. S2CID 23886192.
[6]
Proietto J, Rissanen A, Harp JB, Erondu N, Yu Q, Suryawanshi S, Jones ME, Johnson-Levonas AO, Heymsfield SB, Kaufman KD, Amatruda JM (August 2010). "A clinical trial assessing the safety and efficacy of the CB1R inverse agonist taranabant in obese and overweight patients: low-dose study". International Journal of Obesity. 34 (8): 1243–54. doi:10.1038/ijo.2010.38. PMID 20212496. S2CID 23352608.

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