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Gefitinib

Cayman Chemical Item Number 13166

Iressa™; ZD1839 (CAS 184475-35-2)

Gefitinib (CAS 184475-35-2)

See more	Inhibitors (493) Cancer (606) Signal Transduction (314)

Description

Overactivity of the epidermal growth factor receptor-associated tyrosine kinase (EGFR-TK) has been associated with a number of cancers and thus TK inhibitors could be potential therapeutic agents to prevent malignant growth.¹ Gefitinib is a selective EGFR-TK inhibitor that blocks the growth of GEO colon cancer, ZR-75-1 and MCF-10A Ha-ras breast cancer, and OVCAR-3 ovarian cancer cell lines with IC₅₀s ranging between 0.2-0.4 µM.² By interfering with the intracellular kinase domain, gefitinib prevents EGFR autophosphorylation and prevents downstream signal transduction. Gefitinib has been used to treat advanced (or recurrent) non-small cell lung cancer. However, the FDA retracted its general approval for this compound (Iressa™) when a phase III trial failed to demonstrate an overall survival benefit.³ Gefitinib appears to be most efficacious in treating certain EGFR gene mutations that are prevalent in Asian populations.^4,5

1 Sausville, E.A., Elsayed, Y., Monga, M., et al. Signal transduction-directed cancer treatments. Annu Rev Pharmacol Toxicol 43 199-231 (2003).

2 Ciardiello, F., Caputo, R., Bianco, R., et al. 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 6 2053-2063 (2000).

3 Gerber, D.E. EGFR inhibition in the treatment of non-small cell lung cancer. Drug Dev Res 69(6) 359-372 (2008).

4 Yang, C., Hung, J., Lai, C., et al. Gefitinib as first-line therapy for advanced or metastatic non-small cell lung cancer patients in southern Taiwan. Kaohsiung J Med Sci 26(1) 1-7 (2010).

5 Uruga, H., Kishi, K., Fujii, T., et al. Efficacy of gefitinib for elderly patients with advanced non-small cell lung cancer harboring epidermal growth factor receptor gene mutations: A retrospective analysis. Intern Med 49 103-107 (2010).

Synonyms	Iressa™ ZD1839
Formal Name	N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-4-quinazolinamine
CAS Number	184475-35-2
Molecular Formula	C₂₂H₂₄ClFN₄O₃
Formula Weight	446.9
Formulation	A crystalline solid
Purity	≥98%
Stability	2 years
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard COC1=CC2=C(C(NC3=CC=C(F)C(Cl)=C3)=NC=N2)C=C1OCCCN4CCOCC4

Background Reading

Gerber, D.E. EGFR inhibition in the treatment of non-small cell lung cancer. Drug Dev Res 69(6) 359-372 (2008).

Uruga, H., Kishi, K., Fujii, T., et al. Efficacy of gefitinib for elderly patients with advanced non-small cell lung cancer harboring epidermal growth factor receptor gene mutations: A retrospective analysis. Intern Med 49 103-107 (2010).

Yang, C., Hung, J., Lai, C., et al. Gefitinib as first-line therapy for advanced or metastatic non-small cell lung cancer patients in southern Taiwan. Kaohsiung J Med Sci 26(1) 1-7 (2010).

Sausville, E.A., Elsayed, Y., Monga, M., et al. Signal transduction-directed cancer treatments. Annu Rev Pharmacol Toxicol 43 199-231 (2003).

Ciardiello, F., Caputo, R., Bianco, R., et al. 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 6 2053-2063 (2000).

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Size	Price	Quantity	Subtotal
250 mg	$66.00		$0.00
500 mg	$125.00		$0.00
1 g	$238.00		$0.00
5 g	$1,056.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-02-12. Prices are subject to change without notice.

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