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504595 Bcr-abl Inhibitor IV, Imatinib - CAS 220127-57-1 - Calbiochem

504595
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Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
220127-57-1C₂₉H₃₁N₇O • CH₃SO₃H

Products

Catalogue NumberPackaging Qty/Pack
5.04595.0001 Glass bottle 50 mg
Description
OverviewA 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.
Catalogue Number504595
Brand Family Calbiochem®
SynonymsAbl Inhibitor V, PDGFR Tyrosine Kinase Inhibitor XXIV, c-Kit Inhibitor IV, STI571, 4-((4-Methyl-1-piperazinyl)methyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamide, Methanesulfonate
References
ReferencesLin, Y.L., et al. 2013. Proc. Natl. acad. Sci. USA 110, 1664.
Okada, M., et al. 2004. Blood 103, 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. Science 289, 1938.
Buchdunger, E., et al. 2000. J. Pharmacol. Exp. Ther. 295, 139.
Carroll. M., et al. 1997. Blood 90, 4947.
Zimmermann, J., et al. 1997. Bioorg. Med. Chem. Lett. 7, 187.
Druker, B.J., et al. 1996. Nat. Med. 2, 561.
Product Information
CAS number220127-57-1
FormWhite solid
Hill FormulaC₂₉H₃₁N₇O • CH₃SO₃H
Hygroscopic Hygroscopic
ReversibleY
Structure formula ImageStructure formula Image
Quality LevelMQ100
Applications
Biological Information
Primary TargetAbl
Secondary targetPDGFR, c-kit
Purity≥99% by HPLC
Physicochemical Information
Cell permeableY
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
Safety Information
Product Usage Statements
Storage and Shipping Information
Ship Code Ambient Temperature Only
Toxicity Standard Handling
Storage +2°C to +8°C
Protect from Light Protect from light
Hygroscopic Hygroscopic
Do not freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Packaging Information
Packaged under inert gas Packaged under inert gas
Transport Information
Supplemental Information
Specifications
Global Trade Item Number
Catalogue Number GTIN
5.04595.0001 04055977243901

Documentation

Bcr-abl Inhibitor IV, Imatinib - CAS 220127-57-1 - Calbiochem SDS

Title

Safety Data Sheet (SDS) 

References

Reference overview
Lin, Y.L., et al. 2013. Proc. Natl. acad. Sci. USA 110, 1664.
Okada, M., et al. 2004. Blood 103, 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. Science 289, 1938.
Buchdunger, E., et al. 2000. J. Pharmacol. Exp. Ther. 295, 139.
Carroll. M., et al. 1997. Blood 90, 4947.
Zimmermann, J., et al. 1997. Bioorg. Med. Chem. Lett. 7, 187.
Druker, B.J., et al. 1996. Nat. Med. 2, 561.
Data Sheet

Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

Revision01-July-2013 JSW
SynonymsAbl Inhibitor V, PDGFR Tyrosine Kinase Inhibitor XXIV, c-Kit Inhibitor IV, STI571, 4-((4-Methyl-1-piperazinyl)methyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamide, Methanesulfonate
DescriptionA 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.
FormWhite solid
Intert gas (Yes/No) Packaged under inert gas
CAS number220127-57-1
Structure formulaStructure formula
Purity≥99% by HPLC
SolubilityH₂O (100 mg/ml)
Storage Protect from light
+2°C to +8°C
Hygroscopic
Do Not Freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Toxicity Standard Handling
ReferencesLin, Y.L., et al. 2013. Proc. Natl. acad. Sci. USA 110, 1664.
Okada, M., et al. 2004. Blood 103, 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. Science 289, 1938.
Buchdunger, E., et al. 2000. J. Pharmacol. Exp. Ther. 295, 139.
Carroll. M., et al. 1997. Blood 90, 4947.
Zimmermann, J., et al. 1997. Bioorg. Med. Chem. Lett. 7, 187.
Druker, B.J., et al. 1996. Nat. Med. 2, 561.