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Rimonabant (SR141716)

CAT: 1568-C09042-50mgSize: 50 mgDry Ice: YesHazardous: No
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CAT#:1568-C09042-50mgSize:50 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
168273-06-1
Target
Cannabinoid Receptor
Applications
Neuronal Signaling
Smiles
CC1=C (N (N=C1C (=O) NN2CCCCC2) C3=C (C=C (C=C3) Cl) Cl) C4=CC=C (C=C4) Cl
Molecular Formula
C22H21Cl3N4O
Additionnal Information
Rimonabant (SR141716) is a selective antagonist of CB1 with IC50 of 13.6 nM and EC50 of 17.3 nM in hCB1 transfected HEK 293 membrane. Rimonabant is also a dual inhibitor of acyl CoA:cholesterol acyltransferases (ACAT) 1 and 2 and inhibits mycobacterial MmpL3.
Storage Conditions
2 years -80 in solvent

Chemical Information

Rimonabant

Rimonabant is a 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 It was later withdrawn from market due to CNS-related adverse effects including depression and suicidal ideation. It has a role as an appetite depressant, a CB1 receptor antagonist and an anti-obesity agent. It is a dichlorobenzene, a member of pyrazoles, a carbohydrazide, an amidopiperidine and a member of monochlorobenzenes.

CAS Number168273-06-1
PubChem CID104850
IUPAC Name5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
Molecular FormulaC22H21Cl3N4O
Molecular Weight463.8
XLogP6.5
Topological Polar Surface Area50.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Heavy Atom Count30
Formal Charge0
Complexity583
SMILES
CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)Cl
InChI
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)
InChIKey
JZCPYUJPEARBJL-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Rimonabant
CAS: 168273-06-1
CID: 104850
Formula: C22H21Cl3N4O
MW: 463.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight463.8
XLogP36.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass462.078094
Monoisotopic Mass462.078094
Topological Polar Surface Area50.2 Ų
Heavy Atom Count30
Formal Charge0
Complexity583
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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