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184475-35-2

184475-35-2 structure
184475-35-2 structure
  • Name: Gefitinib
  • Chemical Name: gefitinib
  • CAS Number: 184475-35-2
  • Molecular Formula: C22H24ClFN4O3
  • Molecular Weight: 446.902
  • Catalog: API Antineoplastic agents Tinic antineoplastic agents
  • Create Date: 2018-02-07 08:00:00
  • Modify Date: 2024-01-02 16:57:52
  • Gefitinib (ZD1839) is a EGFR tyrosine kinase inhibitor, with IC50 of 2-37 nM in NR6wtEGFR cells.
Name gefitinib
Synonyms Iressa
N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-4-quinazolinamine
N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamide
MFCD04307832
Irressat
N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(morpholin-4-yl)propoxy]quinazolin-4-amine
N-(3-chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
N-(3-Chlor-4-fluorphenyl)-7-methoxy-6-[3-(morpholin-4-yl)propoxy]chinazolin-4-amin
N-(3-Chlor-4-fluorphenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)chinazolin-4-amin
N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine
N-(3-chloro-4-fluorophényl)-7-méthoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
ZD-1839
Gefitinib
4-Quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-
N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
ZD1839
Description Gefitinib (ZD1839) is a EGFR tyrosine kinase inhibitor, with IC50 of 2-37 nM in NR6wtEGFR cells.
Related Catalog
Target

EGFR
In Vitro Gefitinib (0.01-0.1 mM) results in increased phosphotyrosine load of the receptor, increased signalling to ERK and stimulation of proliferation and anchorage-independent growth, presumably by inducing EGFRvIII dimerisation in long-term exposure of EGFRvIII-expressing cells. On the other hand, gefitinib (1-2 mM) significantly decreases EGFRvIII phosphotyrosine load, EGFRvIII-mediated proliferation and anchorage-independent growth[1]. Gefitinib (ZD1839) inhibits the monolayer growth of these EGF-driven untransformed cells with IC50 of 20 nM[2]. Gefitinib leads to an inhibition of CALU-3 and GLC82 cell proliferation, with an IC50 of 2 μM[3].
In Vivo Gefitinib (150 mg/kg, p.o.) in conbination with Metformin induces a significant reduction in tumor growth in nude mice bearing H1299 or CALU-3 GEF-R cells that are grown subcutaneously as tumor xenografts[3]. In irradiated rats, Gefitinib treatment augmentes lung inflammation, including inflammatory cell infiltration and pro-inflammatory cytokine expression, while Gefitinib treatment attenuates fibrotic lung remodeling due to the inhibition of lung fibroblast proliferation[4].
Cell Assay Cancer cells are seeded in 96-well plates and are treated with different doses of Gefitinib (0.01-20 μM), Metformin or both for 72 hours. Cell proliferation is measured with the MTT assay. The IC50 values are determined by interpolation from the dose-response curves. Results represent the median of 3 separate experiments each conducted in quadruplicate. The results of the combined treatment are analyzed according to the method of Chou and Talalay by using the CalcuSyn software program[3].
Animal Admin Mice[3] Four- to 6-week old female balb/c athymic (nu+/nu+) mice are acclimatized for 1 week before being injected with cancer cells and injected subcutaneously with 107 H1299 and CALU-3 GEF-R cells that has been resuspended in 200 μL of Matrigel. When established tumors of approximately 75 mm3 in diameter are detected, mice are left untreated or treated with oral administrations of metformin (200 mg/mL metformin diluted in drinking water and present throughout the experiment), gefitinib (150 mg/kg daily orally by gavage), or both for the indicated time periods. Each treatment group consists of 10 mice. Tumor volume is measured using the formula π/6×larger diameter×(smaller diameter)2. Rats[4] The rats are randomly assigned to 1 of 4 experimental groups: 1) the unirradiated rats treated with oral administration of vehicle (0.1% Tween 80) once daily; 2) the unirradiated rats treated with oral administration of gefitinib (50 mg/kg/day) once daily; 3) the irradiated rats treated with oral administration of vehicle once daily; 4) the irradiated rats treated with oral administration of gefitinib once daily. Each experimental group comprised 5-6 rats and all treatments are delivered for 14 days.
References

[1]. Pedersen MW, et al. Differential response to gefitinib of cells expressing normal EGFR and the mutant EGFRvIII. Br J Cancer. 2005 Oct 17;93(8):915-23.

[2]. Moasser MM, et al. The tyrosine kinase inhibitor ZD1839 ("Iressa") inhibits HER2-driven signaling and suppresses the growth of HER2-overexpressing tumor cells. Cancer Res. 2001 Oct 1;61(19):7184-8.

[3]. Morgillo F, et al. Synergistic effects of metformin treatment in combination with gefitinib, a selective EGFR tyrosine kinase inhibitor, in LKB1 wild-type NSCLC cell lines. Clin Cancer Res. 2013 Jul 1;19(13):3508-19.

[4]. Miyake K, et al. Epidermal growth factor receptor-tyrosine kinase inhibitor (gefitinib) augments pneumonitis, but attenuates lung fibrosis in response to radiation injury in rats. J Med Invest. 2012;59(1-2):174-85.

[5]. Noh CK, et al. Simultaneous quantification of volitinib and gefitinib in rat plasma by HPLC-MS/MS for application to a pharmacokinetic study in rats. J Sep Sci. 2017 Jul 27.

[6]. Dhar D, et al. Liver Cancer Initiation Requires p53 Inhibition by CD44-Enhanced Growth Factor Signaling. Cancer Cell. 2018 Jun 11;33(6):1061-1077.e6.
Density 1.3±0.1 g/cm3
Boiling Point 586.8±50.0 °C at 760 mmHg
Melting Point 119-1200C
Molecular Formula C22H24ClFN4O3
Molecular Weight 446.902
Flash Point 308.7±30.1 °C
Exact Mass 446.152100
PSA 68.74000
LogP 4.11
Vapour Pressure 0.0±1.6 mmHg at 25°C
Index of Refraction 1.621
Storage condition Store at RT
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H315-H319-H335
Precautionary Statements P301 + P312 + P330-P305 + P351 + P338
Hazard Codes Xi
Risk Phrases R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Phrases S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS HP1149700
HS Code 29143900
HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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