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

• ChemBase ID: 171534
• Molecular Formular: C29H31N7O2
• Molecular Mass: 509.60214
• Monoisotopic Mass: 509.25392327
• SMILES: C1CN(CC[N+]1(Cc1ccc(cc1)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1cccnc1)C)[O-])C
• Canonical SMILES: CN1CC[N+](CC1)([O-])Cc1ccc(cc1)C(=O)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)20-36(38)16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)
• InChIKey: JOLLULXEPUYESM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 938082-57-6
• PubChem SID: 164227444
• PubChem CID: 71749456

CALCULATED PROPERTIES

• Acid pKa: 12.453271
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 1.950869
• LogD (pH = 7.4): 3.1635416
• Log P: 3.2532978
• Molar Refractivity: 150.9742 cm^3
• Polarizability: 57.20211 Å^3
• Polar Surface Area: 109.92 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I268005

Imatinib (Piperidine)-1-oxide is an impurity of Imatinib (Gleevec) (G407000). Imatinib impurity C.

REFERENCES

• Taruns, C., et al.: Bioorg. Chem., 16, 38 (1988)
• Cohen, M., et al.: Clin. Cancer Res., 8, 935 (1988)
• Gschwind, H., et al.: Drug Metab. Dispos., 33, 1503 (1988)
• Peng, B., et al.: Clin. Pharmacokinet., 44, 879 (1988)