4-(3-Chloro-4-fluorophenylamino)-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline hydrochloride Chemical Properties

storage temp. 

Store at -20°C

solubility 

insoluble in EtOH; ≥4.28 mg/mL in H2O with gentle warming and ultrasonic; ≥6.9 mg/mL in DMSO with gentle warming

form 

Powder

color 

White to off-white

4-(3-Chloro-4-fluorophenylamino)-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline hydrochloride Usage And Synthesis

Uses

Gefitinib hydrochloride (ZD1839 hydrochloride) is a potent, selective and orally active EGFR tyrosine kinase inhibitor with an IC50 of 33 nM. Gefitinib hydrochloride selectively inhibits EGF-stimulated tumor cell growth (IC50 of 54 nM) and that blocks EGF-stimulated EGFR autophosphorylation in tumor cells. Gefitinib hydrochloride also induces autophagy. Gefitinib hydrochloride has antitumour activity[1][2].

Biological Activity

the egfr is a mr 170,000 transmembrane glycoprotein with an external binding domain and an intracellular tyrosine kinase domain. gefitinib (zd-1839, iressa) is an epidermal growth factor receptor-selective tyrosine kinase inhibitor.

in vitro

gefitinib inhibited colony formation in soft agar in a dose dependent manner in all cancer cell lines. however, treatment with higher doses resulted in a 2–4-fold increases in apoptosis. dose-dependent supra-additive increase in growth inhibition was observed when cancer cells were treated with totoxic drugs and gefitinib. the combined treatment markedly enhanced apoptotic cell death induced by single agent treatment [1].

in vivo

gefitinib treatment of nude mice bearing established human geo colon cancer xenografts revealed a reversible dose-dependent inhibition of tumor growth because geo tumors resumed the growth rate of controls at the end of the treatment [1].

target

IC 50

EGFR

References

[1] ciardiello f, caputo r, bianco r, damiano v, pomatico g, de placido s, bianco ar, tortora g. antitumor effect and potentiation of cytotoxic drugs activity in human cancer cells by zd-1839 (iressa), an epidermal growth factor receptor-selective tyrosine kinase inhibitor. clin cancer res. 2000;6(5):2053-63.
[2] cantarini mv, mcfarquhar t, smith rp, bailey c, marshall al. relative bioavailability and safety profile of gefitinib administered as a tablet or as a dispersion preparation via drink or nasogastric tube: results of a randomized, open-label, three-period crossover study in healthy volunteers. clin ther. 2004;26(10):1630-6.

4-(3-Chloro-4-fluorophenylamino)-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline hydrochloride(184475-55-6)Related Product Information

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