Rimonabant

Rimonabant
Clinical data
AHFS/Drugs.com	Consumer Drug Information
License data	EU EMA: by INN;
Pregnancy; category	Not assigned, use not recommended;
Routes of; administration	Oral
ATC code	A08AX01 (WHO) ;
Legal status
Legal status	Withdrawn from European and Brazilian markets; not approved elsewhere;
Pharmacokinetic data
Bioavailability	Undetermined
Protein binding	Nearly 100%
Metabolism	Hepatic, CYP3A4 involved
Elimination half-life	Variable:; 6 to 9 days with normal BMI; 16 days if BMI >30
Excretion	Fecal (86%) and renal (3%)
Identifiers
	IUPAC name 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide;
CAS Number	168273-06-1 ; HCl: 158681-13-1 ;
PubChem CID	104850;
IUPHAR/BPS	743;
DrugBank	DB06155 ;
ChemSpider	94641 ;
UNII	RML78EN3XE; HCl: HL0V2LQZ09 ;
KEGG	D05731 ;
ChEMBL	ChEMBL111 ;
CompTox Dashboard (EPA)	DTXSID3046453 ;
ECHA InfoCard	100.210.978
Chemical and physical data
Formula	C22H21Cl3N4O
Molar mass	463.79 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(NN1CCCCC1)c4nn(c2ccc(Cl)cc2Cl)c(c3ccc(Cl)cc3)c4C;
	InChI 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) ; Key:JZCPYUJPEARBJL-UHFFFAOYSA-N ;
	(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as SR141716; trade names Acomplia, Zimulti)^[3] is an anorectic antiobesity drug approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious psychiatric side effects; it was never approved in the United States.^[1]^[2] Rimonabant is an inverse agonist for the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]

^ ^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.
^ ^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.
^ "Rimonabant". AdisInsight. Retrieved 21 February 2017.
^ 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.
^ "European Approval Comes Early for Sanofi-Aventis' Acomplia". IHS. June 23, 2006.

[Sam2011rev-1] 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.

[Moreira2009-2] 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.

[pmid19597516-4] 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.

[IHS-5] "European Approval Comes Early for Sanofi-Aventis' Acomplia". IHS. June 23, 2006.

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