Taranabant

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Taranabant
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Clinical data
Routes of
administration		Oral
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Legal status
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  • Investigational (failed)
Identifiers
  • N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyanophenyl)-2-butanyl]-2-methyl-2-{[5-(trifluoromethyl)-2-pyridinyl]oxy}propanamide
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Chemical and physical data
FormulaC27H25ClF3N3O2
Molar mass515.96 g·mol−1
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  • 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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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.

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

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content."Press release by Merck". Retrieved 4 October 2008.
  4. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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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