1-{1-[4,4-bis(4-fluorophenyl)butyl](3,3,4,5,5-2H5)piperidin-4-yl}-2,3-dihydro-1H-1,3-benzodiazol-2-one

• ChemBase ID: 176728
• Molecular Formular: C28H29F2N3O
• Molecular Mass: 461.5461664
• Monoisotopic Mass: 461.227869
• SMILES: c1c(ccc(c1)C(CCCN1CCC(CC1)n1c2c([nH]c1=O)cccc2)c1ccc(cc1)F)F
• Canonical SMILES: Fc1ccc(cc1)C(c1ccc(cc1)F)CCCN1CCC(CC1)n1c(=O)[nH]c2c1cccc2
• InChI: InChI=1S/C28H29F2N3O/c29-22-11-7-20(8-12-22)25(21-9-13-23(30)14-10-21)4-3-17-32-18-15-24(16-19-32)33-27-6-2-1-5-26(27)31-28(33)34/h1-2,5-14,24-25H,3-4,15-19H2,(H,31,34)
• InChIKey: YVUQSNJEYSNKRX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{1-[4,4-bis(4-fluorophenyl)butyl](3,3,4,5,5-^2H₅)piperidin-4-yl}-2,3-dihydro-1H-1,3-benzodiazol-2-one
• IUPAC Traditional name: 1-{1-[4,4-bis(4-fluorophenyl)butyl](3,3,4,5,5-^2H₅)piperidin-4-yl}-3H-1,3-benzodiazol-2-one
• Synonyms: 1-[1-[4,4-Bis(4-fluorophenyl)butyl]-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one-d5; 1-[1-[4,4-Bis(p-fluorophenyl)butyl]-4-piperidyl]-2-benzimidazolinone-d5; 1-[4,4-Bis(p-fluorophenyl)butyl]-4-(2-oxo-1-benzimidazolinyl)piperidine-d5; NSC 170984-d5; Orap-d5; Primozide-d5; R 6238-d5; Pimozide-d5

Database IDs

• PubChem SID: 164232638
• PubChem CID: 71751669

CALCULATED PROPERTIES

• Acid pKa: 12.898585
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.0353284
• LogD (pH = 7.4): 4.8004894
• Log P: 5.8257136
• Molar Refractivity: 132.2078 cm^3
• Polarizability: 49.542534 Å^3
• Polar Surface Area: 35.58 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P447802

Labelled analogue of Pimozide, a D2 dopamine receptor antagonist. Pimozide binds with high affinity to the cloned 5-HT7 receptor. Pimozide is also a Ca2+ channel antagonist. Pimozide is used as an antipsychotic.

REFERENCES

• Liu, J., et al.: Br. J. Pharmacol., 126, 245 (1999)
• Richelson, E., et al.: Life Sci., 68, 29 (1999)
• Santi, C., et al.: J. Neurosci., 22, 396 (1999)
• Mariot, P., et al.: J. Biol. Chem., 277, 10824 (1999)
• Nikonenko, I., et al.: Mol. Pharmacol., 68, 84 (2