3672. Erlotinib

Nomenclature

CAS number: 183321-74-6
N-(3-Ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine.
C22H23N3O4; mol wt 393.44.
C 67.16%, H 5.89%, N 10.68%, O 16.27%.

Description and references

Selective epidermal growth factor receptor (EGFR)-tyrosine kinase inhibitor. Prepn: R. C. Schnur, L. D. Arnold, WO 9630347; eidem, US 5747498 (1996, 1998 both to Pfizer). Mechanism of action study: J. D. Moyer et al., Cancer Res. 57, 4838 (1997) PubMed. Enzyme inhibition and antitumor activity: V. A. Pollack et al., J. Pharmacol. Exp. Ther. 291, 739 (1999) PubMed. HPLC determn in plasma: E. R. Lepper et al., J. Chromatogr. B 796, 181 (2003) DOI PubMed. Clinical pharmacokinetics: M. Hidalgo et al., J. Clin. Oncol. 19, 3267 (2001) PubMed. Clinical evaluation in non-small-cell lung cancer: R. Pérez-Soler et al., J. Clin. Oncol. 22, 3238 (2004) DOI PubMed. Review of pharmacology and clinical development: T. E. Kim, J. R. Murren, Curr. Opin. Investig. Drugs 3, 1385-1395 (2002) PubMed; and use in non-small cell lung cancer: F. H. Blackhall et al., Expert Opin. Pharmacother. 6, 995-1002 (2005) DOI PubMed.

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 183319-69-9
CP-358774; OSI-774; Tarceva (OSI).
C22H23N3O4.HCl; mol wt 429.90.
C 61.46%, H 5.63%, N 9.77%, O 14.89%, Cl 8.25%.

Properties

mp 228-230°. pKa (25°): 5.42. Soly in water (pH ≈2): ≈0.4 mg/ml. Slightly sol in methanol. Practically insol in acetonitrile, acetone, ethyl acetate, hexane.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Tyrosine Kinase Inhibitors