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PZ0192

Sigma-Aldrich

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:
Molecular Weight:
530.45
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

color

off-white to light brown

solubility

DMSO: ≥15 mg/mL

storage temp.

room temp

SMILES string

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

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)

InChI key

UBPYILGKFZZVDX-UHFFFAOYSA-N

Gene Information

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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.

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.

Legal Information

Sold for research purposes under agreement from Pfizer Inc.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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)
Takeo Yasu et al.
Biological & pharmaceutical bulletin, 41(2), 254-258 (2017-12-08)
Ponatinib, a novel tyrosine kinase inhibitor marketed in 2016, is a key drug used for treating chronic myeloid leukemia and Philadelphia chromosome-positive acute lymphoblastic leukemia. This study aimed to develop a simple method for determining plasma ponatinib concentration. The analysis
G Carmona et al.
Oncogene, 35(39), 5155-5169 (2016-03-22)
Cancer invasion is a hallmark of metastasis. The mesenchymal mode of cancer cell invasion is mediated by elongated membrane protrusions driven by the assembly of branched F-actin networks. How deregulation of actin regulators promotes cancer cell invasion is still enigmatic.

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