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Gefitinib, 10 mg, Purity 99.7 %  

Gefitinib, 10 mg, Purity 99.7 %

EGFR tyrosine kinase inhibitor, 4-(3-chloro-4-fluoroanilino)- 7-methoxy- 6-(3-morpholino propoxy) quinazoline, Purity > 99,7 %

Synonyms: ZD 1839, ZD1839, IRESSA TM, specific EGFR tyrosine kinase inhibitor, CAS number: 184475-35-2

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PKI-GFTB-010

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190,00 €

Gefitinib, or IRESSATM as it is more commonly called, is an epidermal growth factor receptor tyrosine kinase inhibitor (EGFR-TKI). EGFR is part of the ERBB receptor family, which has four closely related members: EGFR (ERBB1), HER2 (ERBB2), HER3 (ERBB3) and HER4 (ERBB4). These receptors consist of an extracellular ligand-binding domain, a transmembrane domain and an intracellular tyrosine kinase domain. Ligand binding induces dimerization which activates the tyrosine kinase activity. This leads to receptor autophosphorylation and the initiation of signal transduction cascades involved in cell proliferation and survival. EGFR activation has been implicated in processes involved in tumor growth and progression including cell proliferation, inhibition of apoptosis, angiogenesis and metastasis. Gefitinib is an ATP competitive inhibitor of EGFR tyrosine kinaseactivity with an IC50 value of 0.033 µM (EGFR/HER1) and was shown to effectively inhibit HER1-HER2 heterodimers.  HER2 (ErbB2) is inhibited with an IC50 > 3,7 µM. Gefitinib is widely investigated in non-small cancer of the lung, colon cancer, breast cancer and cancer of the head and neck. In non-small cell lung cancer recent data show its benefit to be limited mostly to adenocarcinoma subsets, patients carrying activating HER1-mutations, nonsmokers and patients of japanese origin. Gefitinib shows extensive tissue distribution. Its concentration in tumor tissue was shown to reach 16 µM which exceeds its HER1 IC50 by a factor of 500.

CAS number:    184475-35-2
Synonyms:    ZD 1839, ZD1839
Chemical Name:    4-(3-chloro-4-fluoroanilino)-7-methoxy-6-(3-morpholino-propoxy)quinazoline
Formula:     C22H24ClFN4O3 x 0,5 H20
Molecular Weight:     455.9 g/mol
Long Term Storage:     -200C
Purity:     >99.7% (HPLC)
Appearance:     crystalline, white to off-white solid
Solubility:     soluble in DMSO or glacial acetic acid
1H-NMR:     complies with reference

Please notice: Gefitinib is subject to various Astra Zeneca patents and is intended for research use only. It might not be available in some countries and might not be available to some institutions. IRESSATM is a registered trade mark of Astra Zeneca.

Product specific literature references:

Barker AJ, Gibson KH, Grundy W, Godfrey AA, Barlow JJ, Healy MP, Woodburn JR, Ashton SE, Curry BJ, Scarlett L, Henthorn L, Richards L "Studies leading to the identification of ZD1839 (IRESSA): an orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer" Bioorg. Med. Chem. Lett. 11(14):1911-4

Moulder SL, Yakes FM, Muthuswamy SK, Bianco R, Simpson JF, Arteaga CL (2001) "Epidermal growth factor receptor (HER1) tyrosine kinase inhibitor ZD1839 (Iressa) inhibits HER2/neu (erbB2)-overexpressing breast cancer cells in vitro and in vivo" Cancer Res. 61(24):8887-95

Blackledge G, Averbuch S (2004, review) "Gefitinib (\'Iressa\', ZD1839) and new epidermal growth factor receptor inhibitors" Br. J. Cancer 90(3):566-72.

Li J, Kleeff J, Giese N, Buchler MW, Korc M, Friess H (2004) "Gefitinib (\'Iressa\', ZD1839), a selective epidermal growth factor receptor tyrosine kinase inhibitor, inhibits pancreatic cancer cell growth, invasion, and colony formation" Int. J. Oncol. 25(1):203-10

Paez JG, Janne PA, Meyerson M et al. (2004) "EGFR mutations in lung cancer: correlation with clinical response to gefitinib therapy" Science 304(5676):1497-500

Pao, W., Miller, V, Zakowski, M., et al., (2004) "EGF Receptor gene mutations are common in lung cancers from never smokers and are associated with sensitivity of tumors to gefitinib and erlotinib" Proc. Natl. Acad. Sci. 36, 13306-13311

Chou TY, Chiu CH, Tsai CM et al. (2005) "Mutation in the tyrosine kinase domain of epidermal growth factor receptor is a predictive and prognostic factor for gefitinib treatment in patients with non-small cell lung cancer" Clin Cancer Res 11(10):3750-7

Kobayashi S, Boggon TJ, Halmos B et al. (2005) "EGFR mutation and resistance of non-small-cell lung cancer to gefitinib"  N. Engl. J. Med. 352(8):786-92

Product Citations:

Bill A, Schmitz A, König K, Heukamp LC, Hannam JS, Famulok M. (2012) "Anti-proliferative effect of cytohesin inhibition in gefitinib-resistant lung cancer cells." PLoS One. 7(7):e41179.

Kobayashi M, Miki Y, Ebina M, Abe K, Mori K, Narumi S, Suzuki T, Sato I, Maemondo M, Endo C, Inoue A, Kumamoto H, Kondo T, Yamada-Okabe H, Nukiwa T, Sasano H. (2012) " Carcinoembryonic antigen-related cell adhesion molecules as surrogate markers for EGFR inhibitor sensitivity in human lung adenocarcinoma." Br J Cancer. 107(10):1745-53.

Yu SY, Liu HF, Wang SP, Chang CC, Tsai CM, Chao JI. (2013) "Evidence of securin-mediated resistance to gefitinib-induced apoptosis in human cancer cells." Chem Biol Interact. 203(2):412-22.

Oh S, Nam K, Kim H, Shin I. (2017) "Silencing of Glut1 induces chemoresistance via modulation of Akt/GSK-3β/β-catenin/survivin signaling pathway in breast cancer cells." Arch Biochem Biophys. S0003-9861(17)30263-1

Miao Wang1 and Alex Yuang-Chi Chang1 (2018) "Molecular mechanism of action and potential biomarkers of growth inhibition of synergistic combination of afatinib and dasatinib against gefitinib-resistant non-small cell lung cancer cells"
Oncotarget. 9(23): 16533–16546.

PLEASE NOTE: This product is designed for research purposes and can only be delivered to academic and business customers.  

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