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SML1027

Sigma-Aldrich

Imatinib mesylate

≥98% (HPLC)

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Synonym(s):
4-[(4-Methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-phenyl]benzamide methanesulfonate, 4-[(4-Methylpiperazin-1-yl)methyl]-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide mesylate, CGP 57148, Genfatinib, Glivec, Imatinib methanesulfonate, STI-571
Empirical Formula (Hill Notation):
C29H31N7O · CH4O3S
CAS Number:
Molecular Weight:
589.71
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 10 mg/mL, clear

storage temp.

2-8°C

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)

InChI key

YLMAHDNUQAMNNX-UHFFFAOYSA-N

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Application

Imatinib mesylate (IM) has been used:
  • in sulforhodamine B cell viability assay to study its effect on CD34+ or CD38- and CD34+ or CD38+ cells
  • as an abelson1 (ABL1) kinase inhibitor
  • in circular dichroism analysis to study the effect of IM binding on the secondary structure of the human transferrins

Biochem/physiol Actions

Imatinib mesylate is a tyrosine kinase inhibitor with antineoplastic activity. Imatinib is a potent inhibitor of the Bcr-Abl kinase encoded by the bcr-abl oncogene as well as receptor tyrosine kinases encoded by c-kit and platelet-derived growth factor receptor (PDGFR) oncogenes. Imatinib mesylate inhibition of Bcr-Abl tyrosine kinase created by the Philadelphia chromosome abnormality found in CML decreases proliferation and enhances apoptosis in leukemias CML and ALL. Inhibition of c-kit tyrosine activity inhibits mast-cell and cellular proliferation in those diseases overexpressing c-kit such as gastrointestinal stromal tumor (GIST).

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Other Notes

Imatinib has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the Imatinib probe summary on the Chemical Probes Portal website.

pictograms

Health hazard

signalword

Warning

hcodes

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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