Chemistry:Taranabant

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 ;
PubChem CID	11226090;
ChemSpider	9401143;
UNII	X9U622S114;
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;
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Short description: Chemical compound

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 discovered by Merck & Co.

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

References

↑ "Substituted acyclic sulfonamides as human cannabinoid-1 receptor inverse agonists". Bioorganic & Medicinal Chemistry Letters 17 (8): 2184–7. 2007. doi:10.1016/j.bmcl.2007.01.087. PMID 17293109.
↑ "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. Jun 2007. doi:10.1124/jpet.106.118737. PMID 17327489.
↑ "Press release by Merck". http://www.merck.com/newsroom/press_releases/research_and_development/2008_1002.html.
↑ "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. May 2010. doi:10.1038/ijo.2010.21. PMID 20157323.
↑ "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. June 2010. doi:10.1111/j.1463-1326.2009.01188.x. PMID 20518807.
↑ "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. August 2010. doi:10.1038/ijo.2010.38. PMID 20212496.

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Original source: https://en.wikipedia.org/wiki/Taranabant. Read more

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
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)