Rosonabant

Rosonabant (INN; E-6776) is a drug acting as a CB1 receptor antagonist/inverse agonist that was under investigation by Esteve as an appetite suppressant for the treatment of obesity.[1][2] Development of the drug for clinical use was apparently halted shortly after the related CB1 antagonist rimonabant was discontinued in November 2008, due to the reports of severe psychiatric adverse effects such as anxiety, depression, and suicidal ideation associated with it and with similarly acting agents.[3][4][5]

Rosonabant
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • (±)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(1-piperidinyl)-4,5-dihydro-1H-pyrazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H21Cl3N4O
Molar mass451.78 g·mol−1
3D model (JSmol)
SMILES
  • O=C(NN1CCCCC1)\C4=N\N(c2ccc(Cl)cc2Cl)C(c3ccc(Cl)cc3)C4
InChI
  • InChI=1S/C21H21Cl3N4O/c22-15-6-4-14(5-7-15)20-13-18(21(29)26-27-10-2-1-3-11-27)25-28(20)19-9-8-16(23)12-17(19)24/h4-9,12,20H,1-3,10-11,13H2,(H,26,29)
  • Key:WMMMJGKFKKBRQR-UHFFFAOYSA-N

See also

References
  1. Janero DR, Makriyannis A (March 2009). "Cannabinoid receptor antagonists: pharmacological opportunities, clinical experience, and translational prognosis". Expert Opinion on Emerging Drugs. 14 (1): 43–65. doi:10.1517/14728210902736568. PMID 19249987. S2CID 74250986.
  2. Tim C. Kirkham; S. J. Cooper (2007). Appetite and Body Weight: Integrative Systems and the Development of Anti-Obesity Drugs. Academic Press. p. 325. ISBN 978-0-12-370633-1. Retrieved 12 May 2012.
  3. Heal DJ, Gosden J, Smith SL (December 2009). "Regulatory challenges for new drugs to treat obesity and comorbid metabolic disorders". British Journal of Clinical Pharmacology. 68 (6): 861–74. doi:10.1111/j.1365-2125.2009.03549.x. PMC 2810797. PMID 20002080.
  4. Lee HK, Choi EB, Pak CS (2009). "The current status and future perspectives of studies of cannabinoid receptor 1 antagonists as anti-obesity agents". Current Topics in Medicinal Chemistry. 9 (6): 482–503. doi:10.2174/156802609788897844. PMID 19689362. Archived from the original on 2013-05-22.
  5. Moreira, Fabrício A.; Crippa, José Alexandre S. (June 2009). "The psychiatric side-effects of rimonabant". Revista Brasileira de Psiquiatria. 31 (2): 145–153. doi:10.1590/S1516-44462009000200012. ISSN 1516-4446. PMID 19578688.


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