Taranabant

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Chemical compound

Pharmaceutical compound
Taranabant
Skeletal formula of taranabant
Space-filling model of the taranabant molecule
Clinical data
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • Investigational (failed)
Identifiers
  • N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyanophenyl)-2-butanyl]-2-methyl-2-{[5-(trifluoromethyl)-2-pyridinyl]oxy}propanamide
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.207.983Edit this at Wikidata
Chemical and physical data
FormulaC27H25ClF3N3O2
Molar mass515.96 g·mol−1
3D model (JSmol)
  • 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=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)

Taranabant (codenamedMK-0364) is a cannabinoid receptor type 1 (CB1)inverse agonist that was investigated as a potential treatment forobesity due to itsanorectic effects.[1][2] It was developed byMerck & Co.

In October 2008, Merck stopped itsphase IIIclinical trials with the drug due to high level ofcentral nervous system side effects, mainlydepression andanxiety.[3][4][5][6]

See also

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". Retrieved4 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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