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Merck

SML1027

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
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated

Key Documents

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Product Name

Imatinib mesylate, ≥98% (HPLC)

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

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 10 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

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

signalword

Warning

hcodes

H361d

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

SML1027-BULK: + SML1027-10MG: + SML1027-VAR: + SML1027-100MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000517955
0000517954
0000517954
0000517955
0000487457

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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)
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.
Julien Solinc et al.
Journal of the American Heart Association, 11(7), e023021-e023021 (2022-03-30)
Background Platelet-derived growth factor is a major regulator of the vascular remodeling associated with pulmonary arterial hypertension. We previously showed that protein widely 1 (PW1+) vascular progenitor cells participate in early vessel neomuscularization during experimental pulmonary hypertension (PH) and we
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)
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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