4-{[4-methyl(2H8)piperazin-1-yl]methyl}-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide; methanesulfonic acid

• ChemBase ID: 169639
• Molecular Formular: C30H35N7O4S
• Molecular Mass: 589.7084
• Monoisotopic Mass: 589.24712364
• SMILES: C1CN(CCN1Cc1ccc(cc1)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1cccnc1)C)C.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.CN1CCN(CC1)Cc1ccc(cc1)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1cccnc1)C
• InChI: InChI=1S/C29H31N7O.CH4O3S/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)20-36-16-14-35(2)15-17-36;1-5(2,3)4/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34);1H3,(H,2,3,4)
• InChIKey: YLMAHDNUQAMNNX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[4-methyl(^2H₈)piperazin-1-yl]methyl}-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide; methanesulfonic acid
• IUPAC Traditional name: 4-{[4-methyl(^2H₈)piperazin-1-yl]methyl}-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide; methanesulfonic acid
• Synonyms: 4-[(4-Methyl-1-piperazinyl-d8)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]benzamide Methanesulfonate; CGP 57148B-d8; Gleevac-d8; Glivec-d8; Imatinib-d8 Mesilate; Imatinib-d8 Mesylate; STI 571-d8; Gleevec-d8 Mesylate (Imatinib-d8 Mesylate)

Database IDs

• PubChem SID: 162263771
• PubChem CID: 71317077

CALCULATED PROPERTIES

• Acid pKa: 12.454878
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 1.6563946
• LogD (pH = 7.4): 3.4515045
• Log P: 4.377673
• Molar Refractivity: 148.9293 cm^3
• Polarizability: 57.10315 Å^3
• Polar Surface Area: 86.28 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 148-150°C

Safety Information

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

DETAILS

Toronto Research Chemicals - G407002

A deuterated tyrosine kinase inhibitor. Highly specific for BCR-ABL, the enzyme associated with chronic myelogenous leukemia (CML) and certain forms of acute lymphoblastic leukemia (ALL).

REFERENCES

• Schindler, T., et al.: Science, 289, 1938 (2000)
• Drucker, B.J., et al.: N. Engl. J. Med., 344, 1031 (2000)