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Merck

PZ0192

Bosutinib

≥98% (HPLC)

Synonym(s):

4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile, SKI-606, WAY-173606

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About This Item

Empirical Formula (Hill Notation):
C26H29Cl2N5O3
CAS Number:
380843-75-4
Molecular Weight:
530.45
NACRES:
NA.77
PubChem Substance ID:
329823766
UNSPSC Code:
12352200
MDL number:
MFCD07367846

Key Documents

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InChI

1S/C26H29Cl2N5O3/c1-32-6-8-33(9-7-32)5-4-10-36-25-13-21-18(11-24(25)35-3)26(17(15-29)16-30-21)31-22-14-23(34-2)20(28)12-19(22)27/h11-14,16H,4-10H2,1-3H3,(H,30,31)

SMILES string

COc1cc(Nc2c(cnc3cc(OCCCN4CCN(C)CC4)c(OC)cc23)C#N)c(Cl)cc1Cl

InChI key

UBPYILGKFZZVDX-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

off-white to light brown

solubility

DMSO: ≥15 mg/mL

storage temp.

room temp

Quality Level

100

Gene Information

human ... ABL1(25), HCK(3055), LYN(4067), SRC(6714)

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General description

Bosutinib is a safe oral medicine with good bioavailability. It is effective for treating chronic myeloid leukemia (CML). It is also a potent ATP-competitive inhibitor for Src tyrosine kinase. Bosutinib inhibits epidermal growth factor receptor (EGFR). It suppresses solid tumors associated with breast, pancreas and prostate.

Biochem/physiol Actions

Bosutinib (SKI-606) is an orally active; dual Src/Abl tyrosine kinase inhibitor with potent antiproliferative activity. It does not appear to inhibit c-Kit and PDGRF, which are thought to be the cause of numerous side effects in anticancer treatment with some other tyrosine kinase inhibitors.
Orally active, dual Src/Abl kinase inhibitor with potent antiproliferative activity

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.
This compound is featured on the Abl page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Sigma-Aldrich is a licensed supplier of Bosutinib, providing the authentic Pfizer compound. The material is independently assayed and verified by both Pfizer and Sigma-Aldrich.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319,H413

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

No data available

flash_point_c

No data available

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Certificates of Analysis (COA)

Lot/Batch Number
0000341977
0000341977
0000296407
0000296407
0000225975

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Jun Imagawa et al.
The Lancet. Haematology, 2(12), e528-e535 (2015-12-22)
First-line imatinib treatment can be successfully discontinued in patients with chronic myeloid leukaemia after deep molecular response has been sustained for at least 2 years. We investigated the safety and efficacy of discontinuing second-line or subsequent dasatinib after at least
Phase I study of bosutinib, a src/abl tyrosine kinase inhibitor, administered to patients with advanced solid tumors.
Daud AI, et al.
Clinical Cancer Research, 18(4), 1092-1100 (2012)
Safety and efficacy of bosutinib (SKI-606) in chronic phase Philadelphia chromosome-positive CML patients with resistance or intolerance to imatinib.
Cortes JE, et al.
Blood, 118(17), 4567-4576 (2011)
Sawsan M Amer et al.
Chemistry Central journal, 11(1), 136-136 (2017-12-24)
Masitinib (MST) is a selective tyrosine kinase inhibitor. Validated liquid chromatography tandem mass spectrometric method (LC-MS/MS) was developed for the quantification of MST in rat liver microsomes (RLMs) matrix. The developed method was applied to metabolic stability and excretion rate
Clarissa A Whitehead et al.
Translational oncology, 11(6), 1406-1418 (2018-09-17)
The most common primary central nervous system tumor in adults is the glioblastoma multiforme (GBM). The highly invasive nature of GBM cells is a significant factor resulting in the inevitable tumor recurrence and poor patient prognosis. Tumor cells utilize structures
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