Rimonabant (CHEM019003)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:45:10 UTC
Update Date2016-11-09 01:15:54 UTC
Accession NumberCHEM019003
Identification
Common NameRimonabant
ClassSmall Molecule
DescriptionA carbohydrazide obtained by formal condensation of the carboxy group of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid with the amino group of 1-aminopiperidine. It is a potent and selective cannabinoid receptor 1 (CB1R) antagonist. Besides its antagonistic properties, numerous studies have shown that, at micromolar concentrations rimonabant behaves as an inverse agonist at CB1 receptors. The drug was the first selective CB1 antagonist/inverse agonist introduced into clinical practice to treat obesity and metabolic-related disorders. It was later withdrawn from market due to CNS-related adverse effects including depression and suicidal ideation.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9404100000-b4e952d6cb28f37a5bcfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03xr-0007900000-a3e664246f26a3081b28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-6000900000-c7a63eca60b5ae34236eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qa-9001500000-6c82c44c31b95dd57e6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-c4706c1b75e67ecce758Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0003900000-bd4dcdb5302a69cef5c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4109700000-88f8f41955e94367f7ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1129000000-96c60b95d7ed3d764d64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-b3e191c61bc8a15ef9d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009800000-e0b76fde9003187eb29aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1019200000-431bb0dcf166a142d11eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0003900000-89545a97026620833cccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-1009800000-7405fd5c69583a970fc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-8029100000-d24cda966a3633c58081Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18479080
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.