1-methyl-4-({4-[(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)carbamoyl]phenyl}methyl)piperazin-1-ium-1-olate

• ChemBase ID: 171533
• Molecular Formular: C29H31N7O2
• Molecular Mass: 509.60214
• Monoisotopic Mass: 509.25392327
• SMILES: C1C[N+](CCN1Cc1ccc(cc1)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1cccnc1)C)(C)[O-]
• Canonical SMILES: O=C(c1ccc(cc1)CN1CC[N+](CC1)([O-])C)Nc1ccc(c(c1)Nc1nccc(n1)c1cccnc1)C
• InChI: InChI=1S/C29H31N7O2/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-35-14-16-36(2,38)17-15-35/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)
• InChIKey: MSADRWGPCQTOST-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-4-({4-[(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)carbamoyl]phenyl}methyl)piperazin-1-ium-1-olate
• IUPAC Traditional name: 1-methyl-4-({4-[(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)carbamoyl]phenyl}methyl)piperazin-1-ium-1-olate
• Synonyms: 4-[(4-Methyl-4-oxido-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]benzamide; CGP 71422; Imatinib (Piperidine)-4-oxide

Database IDs

• CAS Number: 571186-91-9
• PubChem SID: 164227443
• PubChem CID: 29982268

CALCULATED PROPERTIES

• Acid pKa: 12.454854
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 2.1214845
• LogD (pH = 7.4): 3.1922278
• Log P: 3.2532978
• Molar Refractivity: 150.9742 cm^3
• Polarizability: 57.203094 Å^3
• Polar Surface Area: 109.92 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 146-149°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - I268000

Imatinib (Piperidine)-4-oxide is an impurity of Imatinib (Gleevec) (G407000). Imatinib impurity D.

REFERENCES

• Dagher, R., et al.: Clin. Cancer Res., 8, 3034 (2002)
• Chourasia, M., et al.: J. Pharm. Pharm. Sci., 6, 33 (2002)
• Deininger, M., et al.: J. Clin. Oncol., 21, 1637 (2002)
• Gschwind, H., et al.: Drug Metab. Dispos., 33, 1503 (2002)