Title: Gefitinib
CAS Registry Number: 184475-35-2
CAS Name: N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-4-quinazolinamine
Synonyms: 4-(3￠-chloro-4￠-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline
Manufacturers' Codes: ZD-1839
Trademarks: Iressa (AstraZeneca)
Molecular Formula: C22H24ClFN4O3
Molecular Weight: 446.90
Percent Composition: C 59.13%, H 5.41%, Cl 7.93%, F 4.25%, N 12.54%, O 10.74%
Literature References: Selective epidermal growth factor receptor (EGFR)-tyrosine kinase inhibitor which blocks signal transduction pathways implicated in the proliferation and survival of cancer cells. Prepn: K. H. Gibson,
WO 9633980;
idem, US 5770599 (1996, 1998 both to Zeneca). LC/MS/MS determn in biological samples: M. Zhao
et al.,
J. Chromatogr. B 819, 73 (2005). Clinical pharmacokinetics and tolerability: H. Swaisland
et al., Clin. Pharmacokinet. 40, 297 (2001).
In vitro and
in vivo inhibition of EGFR-expressing cancer lines: N. G. Anderson
et al., Int. J. Cancer 94, 774 (2001). Proposed mechanism of action: A. Hirata
et al., Cancer Res. 62, 2554 (2002). Clinical study in non-small cell lung cancer: M. G. Kris
et al., J. Am. Med. Assoc. 290, 2149 (2003).
Review: C. L. Arteaga, D. H. Johnson,
Curr. Opin. Oncol. 13, 491-498 (2001). Review of clinical evaluations: D. Raben
et al., Semin. Oncol. 29, Suppl. 4, 37-46 (2002); of use in non-small cell lung cancer: K. Tamura, M. Fukuoka,
Expert Opin. Pharmacother. 6, 985-993 (2005).
Properties: Crystals from toluene, mp 119-120°.
Melting point: mp 119-120°
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Tyrosine Kinase Inhibitors.
