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Gefitinib

Cayman Chemical Item Number 13166

Iressa™; ZD1839 (CAS 184475-35-2)

Gefitinib (CAS 184475-35-2)

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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
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COC1=CC2=C(C(NC3=CC=C(F)​C(Cl)​=C3)​=NC=N2)​C=C1OCCCN4CCOCC4

Background Reading

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).

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).

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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

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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