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5.04595

Bcr-abl Inhibitor IV, Imatinib

Name: Bcr-abl Inhibitor IV, Imatinib
Brand: MM

別名:

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

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この商品について

実験式（ヒル表記法）:

C₂₉H₃₁N₇O · xCH₄O₃S

CAS番号:

220127-57-1

分子量:

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

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特性

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

詳細

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

GHS08

signalword

Warning

hcodes

H361d

pcodes

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

Hazard Classifications

Repr. 2

保管分類

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c