(9R)-3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-4H,6H,7H,8H,9H-pyrido[1,2-a]pyrimidin-4-one

• ChemBase ID: 171278
• Molecular Formular: C23H27FN4O3
• Molecular Mass: 426.4838832
• Monoisotopic Mass: 426.20671896
• SMILES: c1(ccc2c(c1)onc2C1CCN(CC1)CCc1c(nc2n(c1=O)CCC[C@H]2O)C)F
• Canonical SMILES: Fc1ccc2c(c1)onc2C1CCN(CC1)CCc1c(C)nc2n(c1=O)CCC[C@H]2O
• InChI: InChI=1S/C23H27FN4O3/c1-14-17(23(30)28-9-2-3-19(29)22(28)25-14)8-12-27-10-6-15(7-11-27)21-18-5-4-16(24)13-20(18)31-26-21/h4-5,13,15,19,29H,2-3,6-12H2,1H3/t19-/m1/s1
• InChIKey: PMXMIIMHBWHSKN-LJQANCHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9R)-3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-4H,6H,7H,8H,9H-pyrido[1,2-a]pyrimidin-4-one
• IUPAC Traditional name: paliperidone
• Synonyms: (9R)-3-[2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; (+)-9-Hydroxyrisperidone; 9-(R)-Paliperidone; (R)-9-Hydroxy Risperidone

Database IDs

• CAS Number: 130049-85-3
• PubChem SID: 164227188
• PubChem CID: 9802545

CALCULATED PROPERTIES

• Acid pKa: 13.742356
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.3088015
• LogD (pH = 7.4): 0.37811172
• Log P: 1.7565552
• Molar Refractivity: 116.0414 cm^3
• Polarizability: 44.54549 Å^3
• Polar Surface Area: 82.17 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H953355

The R-enantiomer metabolite of Risperidone (R525000), a combined serotonin (5-HT2) and dopamine (D2) receptor antagonist.

REFERENCES

• Tiberghien, F., et al.: Anticancer Drugs, 7, 568 (1996)
• Kansy, M., et al.: J. Med. Chem., 41, 1007 (1996)
• Kerns, E., et al.: J. Pharm. Sci., 90, 1838 (1996)
• Kerr, K., et al.: J. Biol. Chem., 276, 8657 (1996)
• Doran, A., et al.: Drug Metab. Dispos., 33,