Rimonabant (CED0004066)

Record Information
Version1.0
Creation Date2016-05-22 05:45:10 UTC
Update Date2026-08-21 21:37:35 UTC
Accession NumberCHEM019003
Identification
Common NameRimonabant
ClassSmall Molecule
Description
Rimonabant is an organic compound with the chemical formula C22H21Cl3N4O and an average molecular weight of 463.79 g/mol. Rimonabant belongs to the pyrazoles, a subclass of azoles within the organic compounds. It is categorized under the superclass of organoheterocyclic compounds. The compound acts as an antagonist for two recorded protein targets: G-protein coupled receptor 55 (GPR55) and Cannabinoid receptor 1 (CNR1). Rimonabant has been identified in four recorded sources, including healthcare, pharmaceuticals, and veterinary products, specifically as antiobesity preparations excluding diet products. Additionally, it is found in household cleaning and consumer products, such as tobacco product cases, other smoking requisites, and non electric simulated smoking devices. The recorded route of exposure for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamideChEBI
a 281ChEBI
AcompliaChEBI
N-(1-Piperidinyl)-1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxamideChEBI
RimonabantumChEBI
SR 141716ChEBI
SR141716ChEBI
ZimultiChEBI
SR 141716aHMDB
SR141716aHMDB
N-(Piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide hydrochlorideHMDB
Rimonabant hydrochlorideHMDB
RimonabantKEGG
Chemical FormulaC22H21Cl3N4O
Average Molecular Mass463.787 g/mol
Monoisotopic Mass462.078 g/mol
CAS Registry Number168273-06-1
IUPAC Name5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide
Traditional Namerimonabant
SMILESCC1=C(N(N=C1C(=O)NN1CCCCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(Cl)C=C1
InChI IdentifierInChI=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)
InChI KeyJZCPYUJPEARBJL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • 1,3-dichlorobenzene
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Piperidine
  • Heteroaromatic compound
  • Azacycle
  • Hydrazone
  • Organohalogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.002 g/LALOGPS
logP5.47ALOGPS
logP5.91ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)12.42ChemAxon
pKa (Strongest Basic)1.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.16 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity122.83 m³·mol⁻¹ChemAxon
Polarizability47.96 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-9404100000-b4e952d6cb28f37a5bcfNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03xr-0007900000-a3e664246f26a3081b28Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-6000900000-c7a63eca60b5ae34236eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01qa-9001500000-6c82c44c31b95dd57e6cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9000000000-c4706c1b75e67ecce758Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0003900000-bd4dcdb5302a69cef5c1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-4109700000-88f8f41955e94367f7ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1129000000-96c60b95d7ed3d764d64Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0000900000-b3e191c61bc8a15ef9d5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009800000-e0b76fde9003187eb29aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1019200000-431bb0dcf166a142d11eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0003900000-89545a97026620833cccNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03e9-1009800000-7405fd5c69583a970fc0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-8029100000-d24cda966a3633c58081Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1131.0Log mg/kg[640:2000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
260Antiobesity preparations, excl. diet productsHealthcare, pharmaceuticals & veterinary productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
Pathways
2 pathways
Rimonabant Drug Metabolism
Rimonabant Drug Metabolism
Rimonabant Drug Metabolism Action Pathway
Rimonabant Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)0.0778492
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)0.233548
Click to view 3D structureCannabinoid receptor 2P47936Mus musculusPredicted (SEA)0.0778492
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)0.467095
Click to view 3D structureCannabinoid receptor 1P47746Mus musculusPredicted (SEA)0.467095
G-protein coupled receptor 55 structureClick to view 3D structureG-protein coupled receptor 55Q9Y2T6HumansPredicted (SEA)1.79053
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)97.1558
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)72.9447
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)64.8484
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)49.7457
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)37.9126
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)26.313
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)4.67095
Multidrug resistance-associated protein 1 structureClick to view 3D structureMultidrug resistance-associated protein 1P33527HumansPredicted (SEA)5.13805
ATP-binding cassette sub-family C member 4 structureClick to view 3D structureATP-binding cassette sub-family C member 4O15439HumansPredicted (SEA)0.155698
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)307.037
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)452.693
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)538.95
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)671.294
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)122.613
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)724.231
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)1103.43
Click to view 3D structurePeroxisome proliferator-activated receptor deltaQ0ZAQ8Canis lupus familiarisPredicted (SEA)25.7681
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)966.81
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)985.26
Concentrations
Not Available
External Links
DrugBank IDDB06155
HMDB IDHMDB0015623
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00053749
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRimonabant
Chemspider ID94641
ChEBI ID34967
PubChem Compound ID104850
Kegg Compound IDC14319
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11881536
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16934319
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18290515
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5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18654765
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19490094
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20067470
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20828968
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21470203
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21740450
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22182934
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=28429843
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=29407764
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=29797785
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=30077950
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=30300803
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=30556096
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=30682372
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=31522677
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=31898189
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=31981244
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=32085406
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=32417279
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=32463562
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=32512776
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=32781169
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=32885412
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=32904155
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=33121353
30. Huestis MA, Gorelick DA, Heishman SJ, Preston KL, Nelson RA, Moolchan ET, Frank RA: Blockade of effects of smoked marijuana by the CB1-selective cannabinoid receptor antagonist SR141716. Arch Gen Psychiatry. 2001 Apr;58(4):322-8.
31. Maldonado R, Valverde O, Berrendero F: Involvement of the endocannabinoid system in drug addiction. Trends Neurosci. 2006 Apr;29(4):225-32. Epub 2006 Feb 17.
32. Gelfand EV, Cannon CP: Rimonabant: a selective blocker of the cannabinoid CB1 receptors for the management of obesity, smoking cessation and cardiometabolic risk factors. Expert Opin Investig Drugs. 2006 Mar;15(3):307-15.
33. Xie S, Furjanic MA, Ferrara JJ, McAndrew NR, Ardino EL, Ngondara A, Bernstein Y, Thomas KJ, Kim E, Walker JM, Nagar S, Ward SJ, Raffa RB: The endocannabinoid system and rimonabant: a new drug with a novel mechanism of action involving cannabinoid CB1 receptor antagonism--or inverse agonism--as potential obesity treatment and other therapeutic use. J Clin Pharm Ther. 2007 Jun;32(3):209-31.
34. Deadwyler SA, Goonawardena AV, Hampson RE: Short-term memory is modulated by the spontaneous release of endocannabinoids: evidence from hippocampal population codes. Behav Pharmacol. 2007 Sep;18(5-6):571-80.
35. Cahill K, Ussher M: Cannabinoid type 1 receptor antagonists (rimonabant) for smoking cessation. Cochrane Database Syst Rev. 2007 Oct 17;(4):CD005353.