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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:03 UTC
HMDB IDHMDB0015623
Secondary Accession Numbers
  • HMDB15623
Metabolite Identification
Common NameRimonabant
DescriptionRimonabant is an anorectic anti-obesity drug produced and marketed by Sanofi-Aventis. It is an inverse agonist for the cannabinoid receptor CB1. Its main avenue of effect is reduction in appetite. Rimonabant is the first selective CB1 receptor blocker to be approved for use anywhere in the world. Rimonabant is approved in 38 countries including the E.U., Mexico, and Brazil. It was rejected for approval for use in the United States. This decision was made after a U.S. advisory panel recommended the medicine not be approved because it may increase suicidal thinking and depression.
Structure
Data?1582753317
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 Weight463.787
Monoisotopic Molecular Weight462.078094435
IUPAC Name5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide
Traditional Namerimonabant
CAS Registry Number158681-13-1
SMILES
CC1=C(N(N=C1C(=O)NN1CCCCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(Cl)C=C1
InChI Identifier
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)
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.002 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+202.55630932474
DeepCCS[M-H]-200.19830932474
DeepCCS[M-2H]-234.15130932474
DeepCCS[M+Na]+209.23530932474
AllCCS[M+H]+202.832859911
AllCCS[M+H-H2O]+200.632859911
AllCCS[M+NH4]+204.932859911
AllCCS[M+Na]+205.532859911
AllCCS[M-H]-196.332859911
AllCCS[M+Na-2H]-196.132859911
AllCCS[M+HCOO]-196.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RimonabantCC1=C(N(N=C1C(=O)NN1CCCCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(Cl)C=C14570.3Standard polar33892256
RimonabantCC1=C(N(N=C1C(=O)NN1CCCCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(Cl)C=C13505.1Standard non polar33892256
RimonabantCC1=C(N(N=C1C(=O)NN1CCCCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(Cl)C=C13605.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Rimonabant,1TMS,isomer #1CC1=C(C2=CC=C(Cl)C=C2)N(C2=CC=C(Cl)C=C2Cl)N=C1C(=O)N(N1CCCCC1)[Si](C)(C)C3519.2Semi standard non polar33892256
Rimonabant,1TMS,isomer #1CC1=C(C2=CC=C(Cl)C=C2)N(C2=CC=C(Cl)C=C2Cl)N=C1C(=O)N(N1CCCCC1)[Si](C)(C)C3097.6Standard non polar33892256
Rimonabant,1TMS,isomer #1CC1=C(C2=CC=C(Cl)C=C2)N(C2=CC=C(Cl)C=C2Cl)N=C1C(=O)N(N1CCCCC1)[Si](C)(C)C4812.9Standard polar33892256
Rimonabant,1TBDMS,isomer #1CC1=C(C2=CC=C(Cl)C=C2)N(C2=CC=C(Cl)C=C2Cl)N=C1C(=O)N(N1CCCCC1)[Si](C)(C)C(C)(C)C3674.3Semi standard non polar33892256
Rimonabant,1TBDMS,isomer #1CC1=C(C2=CC=C(Cl)C=C2)N(C2=CC=C(Cl)C=C2Cl)N=C1C(=O)N(N1CCCCC1)[Si](C)(C)C(C)(C)C3266.6Standard non polar33892256
Rimonabant,1TBDMS,isomer #1CC1=C(C2=CC=C(Cl)C=C2)N(C2=CC=C(Cl)C=C2Cl)N=C1C(=O)N(N1CCCCC1)[Si](C)(C)C(C)(C)C4765.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rimonabant GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9404100000-b4e952d6cb28f37a5bcf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rimonabant GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rimonabant GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Rimonabant , positive-QTOFsplash10-03xr-0007900000-a3e664246f26a3081b282017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rimonabant 10V, Positive-QTOFsplash10-03dj-6000900000-c7a63eca60b5ae34236e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rimonabant 20V, Positive-QTOFsplash10-01qa-9001500000-6c82c44c31b95dd57e6c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rimonabant 40V, Positive-QTOFsplash10-0002-9000000000-c4706c1b75e67ecce7582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rimonabant 10V, Negative-QTOFsplash10-03di-0003900000-bd4dcdb5302a69cef5c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rimonabant 20V, Negative-QTOFsplash10-03di-4109700000-88f8f41955e94367f7ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rimonabant 40V, Negative-QTOFsplash10-0a4i-1129000000-96c60b95d7ed3d764d642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rimonabant 10V, Positive-QTOFsplash10-03di-0000900000-b3e191c61bc8a15ef9d52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rimonabant 20V, Positive-QTOFsplash10-03di-0009800000-e0b76fde9003187eb29a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rimonabant 40V, Positive-QTOFsplash10-03di-1019200000-431bb0dcf166a142d11e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rimonabant 10V, Negative-QTOFsplash10-03di-0003900000-89545a97026620833ccc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rimonabant 20V, Negative-QTOFsplash10-03e9-1009800000-7405fd5c69583a970fc02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rimonabant 40V, Negative-QTOFsplash10-001i-8029100000-d24cda966a3633c580812021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06155 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06155 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06155
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00053749
Chemspider ID94641
KEGG Compound IDC14319
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRimonabant
METLIN IDNot Available
PubChem Compound104850
PDB IDNot Available
ChEBI ID34967
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:11296091 ]
  2. 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. [PubMed:16483675 ]
  3. 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. [PubMed:16503766 ]
  4. 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. [PubMed:17489873 ]
  5. 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. [PubMed:17762525 ]
  6. Cahill K, Ussher M: Cannabinoid type 1 receptor antagonists (rimonabant) for smoking cessation. Cochrane Database Syst Rev. 2007 Oct 17;(4):CD005353. [PubMed:17943852 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Leite CE, Mocelin CA, Petersen GO, Leal MB, Thiesen FV: Rimonabant: an antagonist drug of the endocannabinoid system for the treatment of obesity. Pharmacol Rep. 2009 Mar-Apr;61(2):217-24. [PubMed:19443932 ]
  2. Lazary J, Juhasz G, Hunyady L, Bagdy G: Personalized medicine can pave the way for the safe use of CB(1) receptor antagonists. Trends Pharmacol Sci. 2011 May;32(5):270-80. doi: 10.1016/j.tips.2011.02.013. Epub 2011 Apr 16. [PubMed:21497918 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered ligand binding
Gene Name:
CNR1
Uniprot ID:
P21554
Molecular weight:
52857.4
References
  1. Shire D, Calandra B, Delpech M, Dumont X, Kaghad M, Le Fur G, Caput D, Ferrara P: Structural features of the central cannabinoid CB1 receptor involved in the binding of the specific CB1 antagonist SR 141716A. J Biol Chem. 1996 Mar 22;271(12):6941-6. [PubMed:8636122 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]