Rimonabant

Rimonabant
Clinical data
AHFS/Drugs.comConsumer Drug Information
License data
Pregnancy
category
  • Not assigned, use not recommended
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • Withdrawn from European and Brazilian markets; not approved elsewhere[1][2]
Pharmacokinetic data
BioavailabilityUndetermined
Protein bindingNearly 100%
MetabolismHepatic, CYP3A4 involved
Elimination half-lifeVariable:
6 to 9 days with normal BMI
16 days if BMI >30
ExcretionFecal (86%) and renal (3%)
Identifiers
  • 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.210.978 Edit this at Wikidata
Chemical and physical data
FormulaC22H21Cl3N4O
Molar mass463.79 g·mol−1
3D model (JSmol)
  • O=C(NN1CCCCC1)c4nn(c2ccc(Cl)cc2Cl)c(c3ccc(Cl)cc3)c4C
  • InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30) checkY
  • Key:JZCPYUJPEARBJL-UHFFFAOYSA-N checkY
  (verify)

Rimonabant (also known as SR141716; trade names Acomplia, Zimulti)[3] is an anorectic antiobesity drug approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious psychiatric side effects; it was never approved in the United States.[1][2] Rimonabant is an inverse agonist for the cannabinoid receptor CB1 and was first-in-class for clinical development.[4][5]

  1. ^ a b Sam AH, Salem V, Ghatei MA (2011). "Rimonabant: From RIO to Ban". Journal of Obesity. 2011: 432607. doi:10.1155/2011/432607. PMC 3136184. PMID 21773005.
  2. ^ a b Moreira FA, Crippa JA (June 2009). "The psychiatric side-effects of rimonabant". Revista Brasileira de Psiquiatria. 31 (2): 145–153. doi:10.1590/s1516-44462009000200012. PMID 19578688.
  3. ^ "Rimonabant". AdisInsight. Retrieved 21 February 2017.
  4. ^ Fong TM, Heymsfield SB (September 2009). "Cannabinoid-1 receptor inverse agonists: current understanding of mechanism of action and unanswered questions". International Journal of Obesity. 33 (9): 947–955. doi:10.1038/ijo.2009.132. PMID 19597516.
  5. ^ "European Approval Comes Early for Sanofi-Aventis' Acomplia". IHS. June 23, 2006.