4-amino-5-chloro-N-[1-(3-methoxypropyl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-7-carboxamide; butanedioic acid

• ChemBase ID: 177082
• Molecular Formular: C22H32ClN3O7
• Molecular Mass: 485.95838
• Monoisotopic Mass: 485.19287806
• SMILES: c1(cc(c2c(c1N)CCO2)C(=O)NC1CCN(CC1)CCCOC)Cl.C(CC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CCC(=O)O.COCCCN1CCC(CC1)NC(=O)c1cc(Cl)c(c2c1OCC2)N
• InChI: InChI=1S/C18H26ClN3O3.C4H6O4/c1-24-9-2-6-22-7-3-12(4-8-22)21-18(23)14-11-15(19)16(20)13-5-10-25-17(13)14;5-3(6)1-2-4(7)8/h11-12H,2-10,20H2,1H3,(H,21,23);1-2H2,(H,5,6)(H,7,8)
• InChIKey: QZRSNVSQLGRAID-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-chloro-N-[1-(3-methoxypropyl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-7-carboxamide; butanedioic acid
• IUPAC Traditional name: prucalopride; succinic acid
• Synonyms: 4-Amino-5-chloro-2,3-dihydro-N-[1-(3-methoxypropyl)-4-piperidinyl]-7-benzofurancarboxamide Butanedioic Acid; R 108512; Resolor; Prucalopride Succinate; Prucalopride Succinat

Database IDs

• CAS Number: 179474-85-2
• PubChem SID: 164232992
• PubChem CID: 9870009

CALCULATED PROPERTIES

• Acid pKa: 14.644509
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.4449213
• LogD (pH = 7.4): -0.8412195
• Log P: 0.7446885
• Molar Refractivity: 100.6711 cm^3
• Polarizability: 37.82579 Å^3
• Polar Surface Area: 76.82 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 196-198°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Succinat

DETAILS

Toronto Research Chemicals - P838950

Prucalopride is a selective 5-HT4 receptor agonist used effective for chronic constipation, but is not currently approved in the U.S. Prucalopride is approved for the treatment of chronic constipation in Europe.

REFERENCES

• Shah, N., et al.: Am. J. Gastroenterol., 103, 1746 (2008)
• McKinnell, R., et al.: J. Med. Chem., 52, 5330 (2008)
• Shah, N., et al.: Am. J. Gastroenterol., 103, 1746 (2008)