4-amino-5-chloro-N-[(3R,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-(13C,2H3)methoxybenzamide

• ChemBase ID: 164786
• Molecular Formular: C23H29ClFN3O4
• Molecular Mass: 466.93811804
• Monoisotopic Mass: 466.18641716
• SMILES: c1cc(ccc1OCCCN1C[C@H]([C@@H](CC1)NC(=O)c1c(cc(c(c1)Cl)N)O[13CH3])OC)F
• Canonical SMILES: CO[C@@H]1CN(CCCOc2ccc(cc2)F)CC[C@H]1NC(=O)c1cc(Cl)c(cc1O[13CH3])N
• InChI: InChI=1S/C23H29ClFN3O4/c1-30-21-13-19(26)18(24)12-17(21)23(29)27-20-8-10-28(14-22(20)31-2)9-3-11-32-16-6-4-15(25)5-7-16/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29)/t20-,22-/m1/s1/i1+1
• InChIKey: DCSUBABJRXZOMT-JHDZSOEHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-chloro-N-[(3R,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-(^1^3C,^2H₃)methoxybenzamide
• IUPAC Traditional name: 4-amino-5-chloro-N-[(3R,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-(^1^3C,^2H₃)methoxybenzamide
• Synonyms: rel-4-Amino-5-chloro-N-[1-[(3R,4S)-3-(4-fluorophenoxy)propyl]-3-(methoxy-13C,d3)-4-piperidinyl]-2-methoxybenzamide; (+/-)-Cisapride-13C,d3; Acenalin-13C,d3; Alimix-13C,d3; Cipril-13C,d3; Coordinax-13C,d3; Prepulsid-13C,d3; Propulsin-13C,d3; cis-2-(Methoxy-13C,d3)-4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]benzamide; Cisapride-13C,d3

Database IDs

• PubChem SID: 162258921
• PubChem CID: 71314874

CALCULATED PROPERTIES

• Acid pKa: 14.575678
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.1796145
• LogD (pH = 7.4): 1.5941783
• Log P: 2.4913588
• Molar Refractivity: 122.9349 cm^3
• Polarizability: 46.753036 Å^3
• Polar Surface Area: 86.05 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Tan Solid
• Melting Point: 90-92°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C496402

Labelled Cisapride, a serotonin 5-HT4 receptro agonist. Used as a Gastroprokinetic.

REFERENCES

• Barone, J.A., et al.: Clin. Pharm., 6, 640 (1987)
• Wiseman, L.R. and Faulds, D., et al.: Drugs, 47, 116 (1994)