Surinabant

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Surinabant
Systematic (IUPAC) name
5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl- N-(1-piperidinyl)-1H-pyrazole-3-carboxamide
Identifiers
CAS number	288104-79-0
ATC code	?
PubChem	9849616
Chemical data
Formula	C₂₃H₂₃Br Cl₂N₄O
Mol. mass	522.264 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Surinabant (SR-147,778) is a cannabinoid receptor type 1 antagonist developed by Sanofi-Aventis.^[1] It is being investigated as a potential treatment for nicotine addiction, to assist smoking cessation. It may also be developed as an anorectic drug to assist with weight loss, however there are already several CB₁ antagonists or inverse agonists on the market or under development for this application,^[2] so surinabant is at present mainly being developed as an anti-smoking drug,^[3] with possible application in the treatment of other addictive disorders such as alcoholism.^[4]^[5] Other potential applications such as treatment of ADHD have also been proposed.^[6]

[edit] References

^ Rinaldi-Carmona M, Barth F, Congy C, Martinez S, Oustric D, Pério A, Poncelet M, Maruani J, Arnone M, Finance O, Soubrié P, Le Fur G. SR147778 [5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide], a new potent and selective antagonist of the CB1 cannabinoid receptor: biochemical and pharmacological characterization. Journal of Pharmacology and Experimental Therapeutics. 2004 Sep;310(3):905-14. PMID 15131245
^ Doggrell SA. Will the new CB1 cannabinoid receptor antagonist SR-147778 have advantages over rimonabant? Expert Opinion on Investigational Drugs. 2005 Mar;14(3):339-42. PMID 15833065
^ Lamota L, Bermudez-Silva FJ, Marco EM, Llorente R, Gallego A, Rodríguez de Fonseca F, Viveros MP. Effects of adolescent nicotine and SR 147778 (Surinabant) administration on food intake, somatic growth and metabolic parameters in rats. Neuropharmacology. 2008 Jan;54(1):194-205. PMID 17720206
^ Gessa GL, Serra S, Vacca G, Carai MA, Colombo G. Suppressing effect of the cannabinoid CB1 receptor antagonist, SR147778, on alcohol intake and motivational properties of alcohol in alcohol-preferring sP rats. Alcohol and Alcoholism. 2005 Jan-Feb;40(1):46-53. PMID 15582988
^ Lallemand F, De Witte P. SR147778, a CB1 cannabinoid receptor antagonist, suppresses ethanol preference in chronically alcoholized Wistar rats. Alcohol. 2006 Jul;39(3):125-34. PMID 17127132
^ Louis C, Terranova JP, Decobert M, Bizot JC, Francon D, Alonso R, Cohen C, Griebel G. Surinabant, a new CB1 receptor antagonist, displays efficacy in animal models of attention deficit/hyperactivity disorder. Behavioural Pharmacology 2005; 16:S42.

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v • d • e Drugs used in addictive disorders (N07B)

Nicotine dependence	Nicotine - Bupropion - Dianicline - Varenicline - Lobeline - Mecamylamine - Clonidine - Surinabant

Alcohol dependence	Disulfiram - Calcium carbimide - Acamprosate - Naltrexone - Nalmefene - Topiramate - Clonidine

Opioid dependence	Buprenorphine - Methadone - Levacetylmethadol - Heroin - Fentanyl - Dihydrocodeine - Dihydroetorphine - Clonidine - Lofexidine - Naltrexone - Ibogaine - 18-Methoxycoronaridine - Morphine - MS-Contin

Stimulant dependence	Dexamphetamine - Bupropion - Vanoxerine - Nocaine - Vigabatrin

Benzodiazepine dependence	Clonidine - Diazepam - Phenytoin - Phenobarbital

Cocaine dependence	Bupropion - Vanoxerine - Nocaine - Baclofen - Vigabatrin

Sedative-Hypnotic dependence	Phenobarbital - Diazepam - Nitrazepam - Clonidine - Chloral Hydrate

v • d • e

Cannabinoids

Plant cannabinoids

CBD • CBDV • CBN • CBG • CBV • CBL • THC • THC-C4 • THCV

Cannabinoid metabolites

11-Hydroxy-THC • 11-nor-9-Carboxy-THC

Endogenous cannabinoids

Arachidonoyl ethanolamide (Anandamide or AEA) • 2-Arachidonoylglycerol (2-AG) • 2-Arachidonyl glyceryl ether (noladin ether) • Virodhamine • N-arachidonoyl-dopamine (NADA)

Synthetic cannabinoid agonists

Classical cannabinoids (Dibenzopyrans)	A-41988 • Ajulemic acid • AM-087 • AM-411 • AM-855 • AM-905 • AM-906 • AM-919 • AM-938 • AM-4030 • AMG-1 • AMG-3 • AMG-36 • AMG-41 • Dexanabinol (HU-211) • DMHP • Dronabinol • HU-210 • JWH-051 • JWH-133 • JWH-139 • L-759,633 • L-759,656 • Levonantradol • Nabilone • Nabitan • O-806 • O-823 • O-1057 • O-1125 • O-1238 • O-2545 • O-2694 • Parahexyl • THC-O-acetate • THC-O-phosphate

Nonclassical cannabinoids	CP 47,497 • CP 55,244 • CP 55,940 • HU-308 • 2-Isopropyl-5-methyl-1-(2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene

Aminoalkylindoles	AM-630 • AM-1241 • JWH-015 • JWH-018 • JWH-073 • JWH-081 • JWH-200 • L-768,242 • Pravadoline • WIN 55,212-2

Aminoalkylpyrroles	JWH-030 • JWH-147 • JWH-307

Eicosanoids	AM-883 • Arachidonyl-2'-chloroethylamide • Arachidonylcyclopropylamide • Methanandamide • O-585 • O-689 • O-1812 • O-1860 • O-1861

Others	BAY 38-7271 • BAY 59-3074 • JWH-171 • O-2220

Endocannabinoid activity enhancers

AM-404 • N-arachidonoyl-serotonin • O-1624 • URB-597 • URB-754

Cannabinoid antagonists and inverse agonists

AM-251 • AM-281 • AM-630 • BML-190 • JTE-907 • LY-320,135 • NESS-0327 • O-1184 • O-2050 • O-2654 • Rimonabant • SLV-319 • SR-144,528 • Surinabant • Taranabant • VCHSR