Canertinib dihydrochloride Chemical Properties

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO: >10mg/mL

form 

solid

color 

Light yellow to green yellow

InChIKey

JZZFDCXSFTVOJY-UHFFFAOYSA-N

SMILES

Cl.Cl.Fc1ccc(Nc2ncnc3cc(OCCCN4CCOCC4)c(NC(=O)C=C)cc23)cc1Cl

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

RTECS 

UC6316110

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

Canertinib dihydrochloride Usage And Synthesis

Uses

The HER family of receptor tyrosine kinases, EGFR, HER2, HER3, and HER4, mediate proliferation, migration, adhesion, differentiation, and survival in many different cell types and have been implicated in the development and progression of a variety of human tumors.Canertinib dihydrochloride is an irreversible quinazoline-based HER family tyrosine kinase inhibitor with IC50 values of 0.8, 19, and 7 nM for blocking in vitro activity of EGFR, HER2, and HER4, respectively. As a broadly applicable anti-cancer agent, it has been used to suppress proliferation of malignant peripheral nerve sheath tumor cells (effective concentration of 250-500 nM), to inhibit growth and induce dose-dependent apoptosis in a panel of neuroblastoma cell lines (IC50s = 0.94-2.45 μM), and to reduce proliferation of acute myeloid leukemia cells (IC50 = 0.27 μM). Canertinib dihydrochloride also displays anti-neoplastic activity towards T98G glioblastoma cells, HCT8 colorectal carcinoma cells, and cells expressing the breast cancer resistance protein.

Uses

CI-1033 is a potent inhibitor of EGFR and ErbB2 with IC50 of 1.5 nM and 9.0 nM, respectively.

Uses

Canertinib Dihydrochloride is a water-soluble, EGFR, HER2, and ErbB-4 tyrosine kinase inhibitor.

Biological Activity

CI-1033 is a potent, irreversible ATP binding site–directed pan-ErbB tyrosine kinase inhibitor with IC50 in the low nanomolar range for EGFR, HER2, and ErbB-4.

Synthesis

4-Chloro-7-fluoroquinazoline was prepared by nitration to produce 4-chloro-7-fluoro-6-nitroquinazoline, which was then condensed with 3-chloro-4-fluoroaniline, substituted with 3-(4-morpholino)-1-propanol, aminoprotected reduction with ethyl trifluoroacetate, Raney Ni catalyzed hydrogenation, and then condensed with acrylic acid, deprotected to obtain the antitumor agent canutinib dihydrochloride in a total yield of about 70%.

in vivo

IC 50

EGFR: 7.4 nM (IC₅₀); ErbB2: 9 nM (IC₅₀)

storage

Store at -20°C

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