Skip to Content
Merck

Key Documents

View All Documentation

5.04595

Bcr-abl Inhibitor IV, Imatinib

Synonym(s):

Bcr-abl Inhibitor IV, Imatinib, 4-((4-Methyl-1-piperazinyl)methyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamide, Methanesulfonate, STI571, Abl Inhibitor V, PDGFR Tyrosine Kinase Inhibitor XXIV, c-Kit Inhibitor IV, STI571, Abl Inhibitor V, PDGFR Tyrosine Kinase Inhibitor XXIV, c-Kit Inhibitor IV, 4-((4-Methyl-1-piperazinyl)methyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamide, Methanesulfonate

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C29H31N7O · xCH4O3S
CAS Number:
220127-57-1
Molecular Weight:
493.60 (free base basis)
MDL number:
MFCD04307699
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥99% (HPLC)
Form:
solid
Storage condition:
OK to freeze, desiccated (hygroscopic), protect from light
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

assay

≥99% (HPLC)

Quality Segment

100

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, desiccated (hygroscopic), protect from light

color

white

solubility

water: 100 mg/mL

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

General description

A cell-permeable, orally bioavailable 2-phenylaminopyrimidine derived compound that competitively binds to ATP-binding site of Abl and stabilizes the inactive conformation, and acts as a highly potent and reversible inhibitor of Abl (IC50 = 38, 25 and 25 nM for v-Abl, Bcr-Abl, and c-Abl, respectively). Also shown to block the activity of PDGFR and c-kit (IC50 = 50 and 100 nM). Exhibits high selectivity over IR, IGF-1R, EGFR, c-Src, JAK-2, PKA, PKC isozymes, CKI, and CKII (IC50 >100 µM). Preferentially blocks the proliferation of leukemic immature cobblestone-forming area cells and Bcr-abl transfected cell lines, M07/p210 and Ba/F3/p185 (~1 -10 µM), and suppresses tumor growth in mice (50 mg/kg, i.p.). Induces apoptosis in Bcr-abl positive cells via intrinsic mitochondrial pathway by down-regulating Bcl-X, promoting cytochrome c release, and activating caspase-9. Does not affect the levels of Bcl-2. Also reported to induce a caspase-independent, necrosis-like programmed cell death mediated by the serine protease activity of Omi/HtrA2.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Abl
Reversible: yes
Secondary Target
PDGFR, c-kit

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Lin, Y.L., et al. 2013. Proc. Natl. acad. Sci. USA110, 1664.
Okada, M., et al. 2004. Blood103, 2299.
Capdeville, R., et al. 2002. Nat. Rev. Drug. Res.1, 493.
Oetzel, C., et al. 2000. Clin Cancer Res.6, 1958.
Schindler, T., et al. 2000. Science289, 1938.
Buchdunger, E., et al. 2000. J. Pharmacol. Exp. Ther.295, 139.
Carroll. M., et al. 1997. Blood90, 4947.

Zimmermann, J., et al. 1997. Bioorg. Med. Chem. Lett.7, 187.
Druker, B.J., et al. 1996. Nat. Med.2, 561.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library