4-amino-5-chloro-N-[(4S)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide hydrate

• ChemBase ID: 179692
• Molecular Formular: C23H31ClFN3O5
• Molecular Mass: 483.9607432
• Monoisotopic Mass: 483.19362701
• SMILES: c1(C(=O)N[C@@H]2C(CN(CC2)CCCOc2ccc(F)cc2)OC)c(cc(c(c1)Cl)N)OC.O
• Canonical SMILES: COC1CN(CCCOc2ccc(cc2)F)CC[C@@H]1NC(=O)c1cc(Cl)c(cc1OC)N.O
• InChI: InChI=1S/C23H29ClFN3O4.H2O/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);1H2/t20-,22?;/m0./s1
• InChIKey: QBYYXIDJOFZORM-CNAJMHLNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-chloro-N-[(4S)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide hydrate
• IUPAC Traditional name: 4-amino-5-chloro-N-[(4S)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide hydrate
• Synonyms: Alimix; Arcasin; Cipril; Cyprid; Fisiogastrol; Kelosal; Kinet; Prepulsid; Propulsin; Propulsid; Pulsitil; Trautil; Cisapride

Database IDs

• CAS Number: 81098-60-4
• PubChem SID: 164235602
• PubChem CID: 51052073

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: 46.752495 Å^3
• Polar Surface Area: 86.05 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: 5HT(4) agonist

Product Information

• Salt Data: H2O
• Application(s): Increases gastrointestinal motility (prokinetic agent); Stimulates gut smooth muscle; Used in the management of GI reflux, dyspepsia

REFERENCES

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• Eur. Pat., 1985, Janssen, 76 530; CA, 99, 194812d, (synth)
• Van Daele, G.H.P. et al., Drug Dev. Res., 1986, 8, 225, (synth, pharmacol)
• Reyntjens, A. et al., Drug Dev. Res., 1986, 8, 251, (rev)
• McCallum, R.W. et al., Drugs, 1988, 36, 652, (rev)
• Woestenborghs, R. et al., J. Chromatogr., 1988, 424, 195, (hplc)
• Hopkins, S.J., Drugs of Today (Barcelona), 1989, 25, 637, (rev)
• Collin, S. et al., J. Mol. Struct., 1989, 214, 159-175, (cryst struct)
• Awouters, F.H.L. et al., Arzneim.-Forsch., 1991, 41, 631, (pharmacol)
• Barone, J.A. et al., Ann. Pharmacother., 1994, 28, 488, (pharmacol)
• Wiseman, L.R. et al., Drugs, 1994, 47, 116, (rev)
• Peeters, O.M. et al., Acta Cryst. C, 1997, 53, 597-599, (cryst struct, tartrate)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1187
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CMS237