4-amino-5-chloro-2-methoxy-N-[(3R,4R)-3-methoxypiperidin-4-yl]benzamide hydrochloride

• ChemBase ID: 175589
• Molecular Formular: C14H21Cl2N3O3
• Molecular Mass: 350.24084
• Monoisotopic Mass: 349.09599691
• SMILES: N1C[C@H]([C@@H](CC1)NC(=O)c1cc(c(cc1OC)N)Cl)OC.Cl
• Canonical SMILES: CO[C@@H]1CNCC[C@H]1NC(=O)c1cc(Cl)c(cc1OC)N.Cl
• InChI: InChI=1S/C14H20ClN3O3.ClH/c1-20-12-6-10(16)9(15)5-8(12)14(19)18-11-3-4-17-7-13(11)21-2;/h5-6,11,13,17H,3-4,7,16H2,1-2H3,(H,18,19);1H/t11-,13-;/m1./s1
• InChIKey: AHDLDHRUBZVPDI-LOCPCMAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-chloro-2-methoxy-N-[(3R,4R)-3-methoxypiperidin-4-yl]benzamide hydrochloride
• IUPAC Traditional name: 4-amino-5-chloro-2-methoxy-N-[(3R,4R)-3-methoxypiperidin-4-yl]benzamide hydrochloride
• Synonyms: rel-4-Amino-5-chloro-2-methoxy-N-[(3R,4S)-3-methoxy-4-piperidinyl]benzamide Hydrochloride; (+/-)-Norcisapride Hydrochloride; cis-Norcisapride Hydrochloride; Nor Cisapride Hydrochloride

Database IDs

• CAS Number: 221180-26-3
• PubChem SID: 164231499
• PubChem CID: 71751174

CALCULATED PROPERTIES

• Acid pKa: 14.575685
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.8786838
• LogD (pH = 7.4): -1.6432239
• Log P: 0.26159963
• Molar Refractivity: 82.0062 cm^3
• Polarizability: 31.289505 Å^3
• Polar Surface Area: 85.61 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMso; Water
• Apperance: Off-White Solid
• Melting Point: 276-278°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - N661460

A metabolite of Cisapride; a biotransformation produced by human cytochrome P 450 enzymes.

REFERENCES

• Wiseman, L., et al.: Drugs, 47, 116 (1994)
• Clarke, S., et al.: Xenobiotica, 28, 1167 (1994)
• Bohets, H., et al.: Br. J. Pharmacol., 129, 1655 (1994)
• Desta, Z., et al.: Drug Metab. Disp., 28, 789 (1994)