3-{2-[(2-methyl-5-{4-[(4-methylpiperazin-1-yl)methyl]benzamido}phenyl)amino]pyrimidin-4-yl}pyridin-1-ium-1-olate

• ChemBase ID: 171535
• Molecular Formular: C29H31N7O2
• Molecular Mass: 509.60214
• Monoisotopic Mass: 509.25392327
• SMILES: C1CN(CCN1Cc1ccc(cc1)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1ccc[n+](c1)[O-])C)C
• Canonical SMILES: CN1CCN(CC1)Cc1ccc(cc1)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1ccc[n+](c1)[O-])C
• InChI: InChI=1S/C29H31N7O2/c1-21-5-10-25(18-27(21)33-29-30-12-11-26(32-29)24-4-3-13-36(38)20-24)31-28(37)23-8-6-22(7-9-23)19-35-16-14-34(2)15-17-35/h3-13,18,20H,14-17,19H2,1-2H3,(H,31,37)(H,30,32,33)
• InChIKey: QEQWNPDNPZKKNH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{2-[(2-methyl-5-{4-[(4-methylpiperazin-1-yl)methyl]benzamido}phenyl)amino]pyrimidin-4-yl}pyridin-1-ium-1-olate
• IUPAC Traditional name: 3-{2-[(2-methyl-5-{4-[(4-methylpiperazin-1-yl)methyl]benzamido}phenyl)amino]pyrimidin-4-yl}pyridin-1-ium-1-olate
• Synonyms: N-[4-Methyl-3-[[4-(1-oxido-3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-4-[(4-methyl-1-piperazinyl)methyl]benzamide; CGP 72383; Imatinib (Pyridine)-N-oxide

Database IDs

• CAS Number: 571186-92-0
• PubChem SID: 164227445
• PubChem CID: 9827642

CALCULATED PROPERTIES

• Acid pKa: 12.453859
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.41812366
• LogD (pH = 7.4): 2.1916316
• Log P: 3.117516
• Molar Refractivity: 152.6188 cm^3
• Polarizability: 57.539276 Å^3
• Polar Surface Area: 98.85 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 226-236°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I268010

matinib (Pyridine)-N-oxide is an impurity of Imatinib (Gleevec) (G407000). Imatinib impurity A.

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)