Surinabant ATC code
5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N -(1-piperidinyl)-1H -pyrazole-3-carboxamide
CAS Number PubChem CID ChemSpider UNII ChEMBL CompTox Dashboard (EPA ) Formula C 23 H 23 Br Cl 2 N 4 O Molar mass 522.27 g·mol−1 3D model (JSmol )
O=C(NN1CCCCC1)c4nn(c2ccc(Cl)cc2Cl)c(c3ccc(Br)cc3)c4CC
InChI=1S/C23H23BrCl2N4O/c1-2-18-21(23(31)28-29-12-4-3-5-13-29)27-30(20-11-10-17(25)14-19(20)26)22(18)15-6-8-16(24)9-7-15/h6-11,14H,2-5,12-13H2,1H3,(H,28,31)
Y Key:HMXDWDSNPRNUKI-UHFFFAOYSA-N
Y
N Y (what is this?)
Surinabant (SR147778 ) 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]
A dose ranging study was done for smoking cessation[7] in 2012; it did not improve success rate, but reduced weight gain. Inhibition of THC effects on heart rate was seen at 20 mg and 60 mg but not 5 mg.[8]
See also [ ]
Cannabinoid receptor antagonist
O-1269
References [ ]
^ Rinaldi-Carmona M, Barth F, Congy C, Martinez S, Oustric D, Pério A, et al. (September 2004). "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". The Journal of Pharmacology and Experimental Therapeutics . 310 (3): 905–14. doi :10.1124/jpet.104.067884 . PMID 15131245 . S2CID 25640461 .
^ Doggrell SA (March 2005). "Will the new CB1 cannabinoid receptor antagonist SR-147778 have advantages over rimonabant?". Expert Opinion on Investigational Drugs . 14 (3): 339–42. doi :10.1517/13543784.14.3.339 . PMID 15833065 . S2CID 33937749 .
^ Lamota L, Bermudez-Silva FJ, Marco EM, Llorente R, Gallego A, Rodríguez de Fonseca F, Viveros MP (January 2008). "Effects of adolescent nicotine and SR 147778 (Surinabant) administration on food intake, somatic growth and metabolic parameters in rats" . Neuropharmacology . 54 (1): 194–205. doi :10.1016/j.neuropharm.2007.07.004 . PMID 17720206 . S2CID 22293050 .
^ Gessa GL, Serra S, Vacca G, Carai MA, Colombo G (2005). "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 . 40 (1): 46–53. doi :10.1093/alcalc/agh114 . PMID 15582988 .
^ Lallemand F, De Witte P (July 2006). "SR147778, a CB1 cannabinoid receptor antagonist, suppresses ethanol preference in chronically alcoholized Wistar rats". Alcohol . 39 (3): 125–34. doi :10.1016/j.alcohol.2006.08.001 . PMID 17127132 .
^ Louis C, Terranova JP, Decobert M, Bizot JC, Françon D, Alonso R, Cohen C, Griebel G (2005). "Surinabant, a new CB1 receptor antagonist, displays efficacy in animal models of attention deficit/hyperactivity disorder". Behavioural Pharmacology . 16 : S42. doi :10.1097/00008877-200509001-00133 .
^ Tonstad S, Aubin HJ (July 2012). "Efficacy of a dose range of surinabant, a cannabinoid receptor blocker, for smoking cessation: a randomized controlled clinical trial" . Journal of Psychopharmacology . 26 (7): 1003–9. doi :10.1177/0269881111431623 . PMID 22219220 . S2CID 39145361 .
^ Klumpers LE, Roy C, Ferron G, Turpault S, Poitiers F, Pinquier JL, et al. (July 2013). "Surinabant, a selective cannabinoid receptor type 1 antagonist, inhibits Δ9-tetrahydrocannabinol-induced central nervous system and heart rate effects in humans" . British Journal of Clinical Pharmacology . 76 (1): 65–77. doi :10.1111/bcp.12071 . PMC 3703229 . PMID 23278647 .
Treatment of drug dependence (N07B )
Nicotine dependence
Bupropion #
Cytisine
Lobeline
Mecamylamine
Varenicline
AA (Clonidine )
Alcohol dependence
AD inhibitor (Disulfiram
Calcium carbimide
Hydrogen cyanamide )
Acamprosate
Opioid antagonists
Topiramate
AA (Clonidine )
Baclofen
Phenibut
Opioid dependence
AA (Clonidine
Lofexidine )
Ibogaine
Opioids
Buprenorphine (+naloxone )
Levacetylmethadol
Methadone
Dihydrocodeine
Dihydroetorphine
Hydromorphone (extended-release)
Morphine (extended-release)
Opioid antagonists (Naltrexone
Nalmefene )
Benzodiazepine dependence
AA (Clonidine )
Benzodiazepines (Diazepam
Lorazepam
Chlordiazepoxide
Oxazepam )
Barbiturates (Phenobarbital )
Cannabinoids
Phytocannabinoids
Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabinols and cannabinodiols Cannabitriols Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols
Delta-9-THC (THC)
THCH
THCP
THCV
Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Arachidonoyl ethanolamide (AEA; anandamide)
2-Arachidonoylglycerol (2-AG)
2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
2-Oleoylglycerol (2-OG)
N-Arachidonoyl dopamine (NADA)
N-Arachidonylglycine (NAGly)
N-Arachidonoyl serotonin (AA-5-HT)
Docosatetraenoylethanolamide (DEA)
Lysophosphatidylinositol (LPI)
Oleamide
Oleoylethanolamide (OEA)
Palmitoylethanolamide (PEA)
RVD-Hpα
Stearoylethanolamide (SEA)
O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols Eicosanoids Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles
A-796,260
A-834,735
FUB-144
UR-144
XLR-11
XLR-12
Tetramethylcyclo- propylindoles Others
Allosteric CBR ligands Endocannabinoid enhancers (inactivation inhibitors) Anticannabinoids (antagonists/inverse agonists/antibodies)
See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
List of: AM cannabinoids
JWH cannabinoids
Designer drugs § Synthetic cannabimimetics
Receptor (ligands )
CB1
Agonists (abridged; see here for more) : 2-AG
2-AGE (noladin ether)
11-Hydroxy-THC
α-Amyrin · β-Amyrin
AB-CHMINACA
AM-1220
AM-1221
AM-1235
AM-2201
AM-2232
Anandamide
AZ-11713908
Cannabinol
CB-13
CP 47,497
CP 55,940
Dimethylheptylpyran
DEA
ECG
EGCG
Epicatechin
Gallocatechol (gallocatechin)
Honokiol
HU-210
JWH-007
JWH-015
JWH-018
JWH-073
Kavain
L-759,633
Levonantradol
Menabitan
Nabilone
Nabitan
NADA
O-1812
Oleamide
Pravadoline
Serinolamide A
THC (dronabinol)
UR-144
WIN 55,212-2
Yangonin
CB2
Agonists: 2-AG
2-AGE (noladin ether)
3,3'-Diindolylmethane
4-O-Methylhonokiol
α-Amyrin · β-Amyrin
A-796,260
A-834,735
A-836,339
AM-1221
AM-1235
AM-1241
AM-2232
Anandamide
AZ-11713908
Cannabinol
Caryophyllene
CB-13
CBS-0550
CP 55,940
GW-405,833 (L-768,242)
GW-842,166X
HU-308
JTE 7-31
JWH-007
JWH-015
JWH-018
JWH-133
L-759,633
L-759,656
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
Virodhamine
NAGly (GPR18 )
Agonists: Abnormal cannabidiol
ACPA
AM251
Anandamide
Cannabidiol
NADGly
THC (dronabinol)
O-1602
GPR55
Agonists: 2-AGE (noladin ether)
Abnormal cannabidiol
AM-251
CP 55,940
Lysophosphatidylinositol
O-1602
Oleoylethanolamide
Palmitoylethanolamide
THC (dronabinol)
GPR119 Unsorted
Transporter (modulators )
eCBTs
Inhibitors:
AM-404
Arachidonoyl serotonin
Cannabidiol
Guineensine
LY-2183240
Paracetamol (acetaminophen)
URB-597
VDM-11
Enzyme (modulators )
FAAH MAGL
Inhibitors:
IDFP
JZL-184
JZL-195
MAFP
URB-602
ABHD6 ABHD12
Inhibitors: Betulinic acid
Maslinic acid
MAFP
Oleanolic acid
Orlistat (tetrahydrolipstatin)
Ursolic acid
Others
Precursors: Phosphatidylethanolamine
NAPE
Diacylglycerol
Others: (directly potentiates activity of 2-AG at CB1 receptor)
(FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)