2,3-dimethoxy-N-{[1-(prop-2-en-1-yl)pyrrolidin-2-yl]methyl}-5-sulfamoylbenzamide

• ChemBase ID: 179483
• Molecular Formular: C17H25N3O5S
• Molecular Mass: 383.4625
• Monoisotopic Mass: 383.15149192
• SMILES: c1(c(c(cc(c1)S(=O)(=O)N)OC)OC)C(=O)NCC1CCCN1CC=C
• Canonical SMILES: C=CCN1CCCC1CNC(=O)c1cc(cc(c1OC)OC)S(=O)(=O)N
• InChI: InChI=1S/C17H25N3O5S/c1-4-7-20-8-5-6-12(20)11-19-17(21)14-9-13(26(18,22)23)10-15(24-2)16(14)25-3/h4,9-10,12H,1,5-8,11H2,2-3H3,(H,19,21)(H2,18,22,23)
• InChIKey: RYJXBGGBZJGVQF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dimethoxy-N-{[1-(prop-2-en-1-yl)pyrrolidin-2-yl]methyl}-5-sulfamoylbenzamide
• IUPAC Traditional name: veralipride
• Synonyms: 5-(Aminosulfonyl)-2,3-dimethoxy-N-[[1-(2-propen-1-yl)-2-pyrrolidinyl]methyl]benzamide; (+/-)-Veralipride; Agreal; LIR 1660; Veralipride

Database IDs

• CAS Number: 66644-81-3
• PubChem SID: 164235393
• PubChem CID: 47979

CALCULATED PROPERTIES

• Acid pKa: 10.059301
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.6941217
• LogD (pH = 7.4): 0.028718939
• Log P: 0.55370927
• Molar Refractivity: 99.5104 cm^3
• Polarizability: 38.82554 Å^3
• Polar Surface Area: 110.96 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V122500

Veralipride, a synthetic benzamide derivative with antidopaminergic action, is effective in reducing the frequency and severity of hot flashes associated with menopausal hypoestrogenism, gaining interest as a non-hormonal treatment for climacteric flushin

REFERENCES

• Casper, R., et al.: Clin. Endocrinol., 22, 293 (1985)
• Melis, G., et al.: J. Clin. Endocrinol. Metab., 66, 964 (1985)
• Stearns, V., et al.: Lancet, 360, 1851 (1985)