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Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2017-12-07 02:52:18 UTC |
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HMDB ID | HMDB0015623 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Rimonabant |
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Description | Rimonabant 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. |
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Structure | |
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Synonyms | Value | Source |
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Acomplia | Kegg | SR 141716 | HMDB | SR 141716a | HMDB | SR141716 | HMDB | SR141716a | HMDB | N-(Piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide hydrochloride | MeSH | Zimulti | MeSH |
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Chemical Formula | C22H21Cl3N4O |
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Average Molecular Weight | 463.787 |
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Monoisotopic Molecular Weight | 462.078094435 |
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IUPAC Name | 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide |
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Traditional Name | rimonabant |
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CAS Registry Number | 158681-13-1 |
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SMILES | CC1=C(N(N=C1C(=O)NN1CCCCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(Cl)C=C1 |
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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) |
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InChI Key | JZCPYUJPEARBJL-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Azoles |
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Sub Class | Pyrazoles |
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Direct Parent | Phenylpyrazoles |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.002 g/L | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Location | Not Available |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Not Available
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Normal Concentrations |
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Blood | Expected but not Quantified | | Not Available | Not Available | Taking drug identified by DrugBank entry DB06155 | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Taking drug identified by DrugBank entry DB06155 | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB06155 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 94641 |
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KEGG Compound ID | C14319 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Rimonabant |
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METLIN ID | Not Available |
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PubChem Compound | 104850 |
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PDB ID | Not Available |
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ChEBI ID | 116088 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Cahill K, Ussher M: Cannabinoid type 1 receptor antagonists (rimonabant) for smoking cessation. Cochrane Database Syst Rev. 2007 Oct 17;(4):CD005353. [PubMed:17943852 ]
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