5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide hydrochloride

• ChemBase ID: 124979
• Molecular Formular: C22H22Cl4N4O
• Molecular Mass: 500.24828
• Monoisotopic Mass: 498.05477206
• SMILES: n1(nc(c(c1c1ccc(cc1)Cl)C)C(=O)NN1CCCCC1)c1c(cc(cc1)Cl)Cl.Cl
• Canonical SMILES: Clc1ccc(cc1)c1c(C)c(nn1c1ccc(cc1Cl)Cl)C(=O)NN1CCCCC1.Cl
• InChI: InChI=1S/C22H21Cl3N4O.ClH/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);1H
• InChIKey: REOYOKXLUFHOBV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide hydrochloride
• IUPAC Traditional name: rimonabant hydrochloride; 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide hydrochloride
• Synonyms: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide hydrochloride; Bethin; Riobant; Slimona; Rimoslim; Zimulti; Rimonabant Hydrochloride; 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide Hydrochloride; Acomplia; SR 141716A; SR 151716A; Rimonabant Hydrochloride

Database IDs

• CAS Number: 158681-13-1
• PubChem SID: 162219332
• PubChem CID: 104849

CALCULATED PROPERTIES

• Acid pKa: 12.421862
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.9079313
• LogD (pH = 7.4): 5.907993
• Log P: 5.9079976
• Molar Refractivity: 122.8308 cm^3
• Polarizability: 48.45934 Å^3
• Polar Surface Area: 50.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >210°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Mechanism of Action: Cannabinoid receptor antagonist; Inverse agonist for the cannabinoid receptor CB1

Product Information

• Salt Data: HCl
• Application(s): Anorectic anti-obesity drug; Appetite reduction drug

DETAILS

Toronto Research Chemicals - R517800

A brain cannabinoid receptor (CB1) antagonist. Antiobesity agent.

REFERENCES

• Dutta, A.K., et al.: Med. Chem. Res., 5, 54 (1994)
• Carai, M.A.M., et al.: Life Sci., 77, 2339 (1994)
• Despres, J.-P., et al.: N. Engl. J. Med., 353, 2121 (1994)
• Seltzman, H.H. et al., Chem. Comm., 1995, 1549-1550, (synth, pmr)
• Eur. Pat., 1995, Sanofi, 656 354; CA, 123, 286006m, (synth, pharmacol)
• Rinaldi-Carmona, M. et al., Life Sci., 1995, 56, 1941-1947, (pharmacol)
• Dutta, A.K. et al., Med. Chem. Res., 1995, 5, 54-62, (synth)
• Brodkin, J. et al., J. Pharmacol. Exp. Ther., 1997, 282, 1526-1532, (pharmacol)