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SML1027

Imatinib mesylate

Name: Imatinib mesylate
Brand: SIGMA

≥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

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Properties

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

Description

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

GHS08

signalword

Warning

hcodes

H361d

pcodes

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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)

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)

Platelet-Derived Growth Factor Receptor Type α Activation Drives Pulmonary Vascular Remodeling Via Progenitor Cell Proliferation and Induces Pulmonary Hypertension.

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

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