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Merck

SML1027

Sigma-Aldrich

Imatinib mesylate

≥98% (HPLC), powder, tyrosine kinase inhibitor

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

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About This Item

Empirical Formula (Hill Notation):
C29H31N7O · CH4O3S
CAS Number:
220127-57-1
Molecular Weight:
589.71
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

Imatinib mesylate, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

[S](=O)(=O)([O-])C.[N+H]1(CCN(CC1)Cc2ccc(cc2)C(=O)Nc3cc(c(cc3)C)Nc4nc(ccn4)c5cnccc5)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 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
GHS08

Signal Word

Warning

Hazard Statements

H361d

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
017M4710V
085M4727V
035M4798V
094M4732V
054M4710V

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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)
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)
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)
Lara S F Konijnenberg et al.
Basic research in cardiology, 118(1), 2-2 (2023-01-14)
Following an acute myocardial infarction, reperfusion of an occluded coronary artery is often accompanied by microvascular injury, leading to worse long-term prognosis. Experimental studies have revealed the potential of tyrosine-kinase inhibitor imatinib to reduce vascular leakage in various organs. Here
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.
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