MilliporeSigma
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SML1027

Sigma-Aldrich

Imatinib mesylate

≥98% (HPLC)

Synonym(s):
CGP 57148, Genfatinib, STI-571, Imatinib methanesulfonate, 4-[(4-Methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-phenyl]benzamide methanesulfonate, Glivec, 4-[(4-Methylpiperazin-1-yl)methyl]-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide mesylate
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

Packaging

10, 100 mg in glass bottle

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Optogenetic reconstitution reveals that Dynein-Dynactin-NuMA clusters generate cortical spindle-pulling forces as a multi-arm ensemble.
Okumura M, et al.
bioRxiv, 277202-277202 (2018)
Ovatodiolide targets chronic myeloid leukemia stem cells by epigenetically upregulating hsa-miR-155, suppressing the BCR-ABL fusion gene and dysregulating the PI3K/AKT/mTOR pathway
Tu Y X, et al.
Oncotarget, 9(3), 3267-3267 (2018)
Tina Baroti et al.
Glia, 64(1), 122-138 (2015-09-09)
Transcription factors of the SoxD protein family have previously been shown to prevent precocious specification and terminal differentiation of oligodendrocyte progenitor cells in the developing spinal cord. Using mice with specific deletion of the SoxD proteins Sox5 and Sox6 in
Wei Ye et al.
Oncotarget, 8(50), 87002-87015 (2016-07-28)
Available therapeutic options for advanced B cell precursor acute lymphoblastic leukemia (pre-B ALL) are limited. Many lead to neutropenia, leaving patients at risk of life-threatening infections and result in bad outcomes. New treatment options are needed to improve overall survival.
Interaction of imatinib mesylate with human serum transferrin: the comparative spectroscopic studies.
Sliwinska-Hill U, et al.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 173, 468-475 (2017)

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