Jump to content
 







Main menu
    


Navigation  


●Main page
 ●Contents
 ●Current events
 ●Random article
 ●About Wikipedia
 ●Contact us
 ●Donate
  



Contribute  


●Help
 ●Learn to edit
 ●Community portal
 ●Recent changes
 ●Upload file
  







Search  

































●Create account

●Log in
 









●Create account
 ● Log in
  



Pages for logged out editors learn more  


●Contributions
 ●Talk
  


















Contents

   



(Top)
  


1 See also  




2 References  













Taranabant






●Français
 ●Српски / srpski
 ●Srpskohrvatski / српскохрватски
 ●Tiếng Việt
 ●中文
  
Edit links
  








●Article
 ●Talk
  
















●Read
 ●Edit
 ●View history
  







Tools
    


Actions  


●Read
 ●Edit
 ●View history
  



General  


●What links here
 ●Related changes
 ●Upload file
 ●Special pages
 ●Permanent link
 ●Page information
 ●Cite this page
 ●Get shortened URL
 ●Download QR code
 ●Wikidata item
  



Print/export  


●Download as PDF
 ●Printable version
  



In other projects  


●Wikimedia Commons
  















Appearance
    

 





From Wikipedia, the free encyclopedia
  

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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.207.983 Edit 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 (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]

See also

[edit]

References

[edit]
  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.
  • ^ 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.
  • ^ "Press release by Merck". Retrieved 4 October 2008.
  • ^ 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.
  • ^ 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.
  • ^ 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.
    • Stub icon

    This cannabinoid related article is a stub. You can help Wikipedia by expanding it.

  • t
  • e

    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Taranabant&oldid=1206031233"
    Categories: 
    ●Anorectics
     ●Cannabinoids
     ●CB1 receptor antagonists
     ●Pyridines
     ●Nitriles
     ●Chlorobenzene derivatives
     ●Trifluoromethyl compounds
     ●Carboxamides
     ●Cannabinoid stubs
     Hidden categories: 
    ●Articles with short description
     ●Short description matches Wikidata
     ●Drugs with non-standard legal status
     ●ECHA InfoCard ID from Wikidata
     ●Articles without EBI source
     ●Chemical pages without DrugBank identifier
     ●Articles without KEGG source
     ●Drugboxes which contain changes to watched fields
     ●All stub articles
      


    ●This page was last edited on 11 February 2024, at 01:42 (UTC).
    ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.


    ●Privacy policy
    ●About Wikipedia
    ●Disclaimers
    ●Contact Wikipedia
    ●Code of Conduct
    ●Developers
    ●Statistics
    ●Cookie statement
    ●Mobile view


    Wikimedia Foundation
    Powered by MediaWiki