Imatinib Mesylate (CGP-57148B, STI-571)

• CAT Number: A000329
• CAS Number: 220127-57-1
• Molecular Formula: C₂₉H₃₁N₇O.CH₄SO₃
• Molecular Weight: 589.71
• Purity: ≥95%
• Target: Bcr-Abl
• Solubility: >29.5mg/mL in DMSO
• Storage: 3 years -20C powder
• IUPAC Name: methanesulfonic acid;4-[(4-methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide
• 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,14-17,20H2,12H3,(H,32,37)(H,31,33,34);1H3,(H,2,3,4)
• InChIKey: YLMAHDNUQAMNNX-UHFFFAOYSA-N
• SMILES: CC1=C(C=C(C=C1)NC(=O)C2=CC=C(C=C2)CN3CCN(CC3)C)NC4=NC=CC(=N4)C5=CN=CC=C5.CS(=O)(=O)O

Imatinib mesylate (CAS 220127-57-1) is a tyrosine kinase inhibitor used primarily in the treatment of leukemia. Chronic Myeloid Leukemia (CML) cells contain a hybrid tyrosine kinase BCR/ABL that works to provide the cancer cell with ATP at an uncontrolled rate. Imatinib mesylate inhbiits this hybrid protein to slow cell growth and promote apoptosis.
Imatinib mesylate binds to the ATP binding site of the BCR/ABL tyrosine kinase and stabilizes its inactive form.

Reference

1.Goldman, J. M., & Melo, J. V. (2003). Chronic Myeloid Leukemia — Advances in Biology and New Approaches to Treatment. New England Journal of Medicine, 349(15), 1451-1464. doi:10.1056/nejmra020777

2.Marcucci, G., Perrotti, D., & Caligiuri, M. A. (2003, April 1). Understanding the Molecular Basis of Imatinib Mesylate Therapy in Chronic Myelogenous Leukemia and the Related Mechanisms of Resistance. Clinical Cancer Research, 9(4), 1248-1252.