Erlotinib

Title: Erlotinib
CAS Registry Number: 183321-74-6
CAS Name: N-(3-Ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine
Molecular Formula: C22H23N3O4
Molecular Weight: 393.44
Percent Composition: C 67.16%, H 5.89%, N 10.68%, O 16.27%
Literature 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). Enzyme inhibition and antitumor activity: V. A. Pollack et al., J. Pharmacol. Exp. Ther. 291, 739 (1999). HPLC determn in plasma: E. R. Lepper et al., J. Chromatogr. B 796, 181 (2003). Clinical pharmacokinetics: M. Hidalgo et al., J. Clin. Oncol. 19, 3267 (2001). Clinical evaluation in non-small-cell lung cancer: R. Pérez-Soler et al., J. Clin. Oncol. 22, 3238 (2004). Review of pharmacology and clinical development: T. E. Kim, J. R. Murren, Curr. Opin. Invest. Drugs 3, 1385-1395 (2002); and use in non-small cell lung cancer: F. H. Blackhall et al., Expert Opin. Pharmacother. 6, 995-1002 (2005).
Derivative Type: Hydrochloride
CAS Registry Number: 183319-69-9
Manufacturers' Codes: CP-358774; OSI-774
Trademarks: Tarceva (OSI)
Molecular Formula: C22H23N3O4.HCl
Molecular Weight: 429.90
Percent Composition: 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.
Melting point: mp 228-230°
pKa: pKa (25°): 5.42
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Tyrosine Kinase Inhibitors.
Ertapenem Erucic Acid Erythritol Erythritol Anhydride Erythrityl Tetranitrate

Erlotinib
Systematic (IUPAC) name
N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)
quinazolin-4-amine
Clinical data
Trade names Tarceva
AHFS/Drugs.com monograph
MedlinePlus a605008
Licence data EMA:Link, US FDA:link
Pregnancy cat. D (US)
Legal status POM (UK) -only (US)
Routes Oral tablets
Pharmacokinetic data
Bioavailability 59%
Protein binding 95%
Metabolism Hepatic (mainly CYP3A4, less CYP1A2)
Half-life 36.2 hrs (median)
Excretion >98% as metabolites, of which >90% via faeces, 9% via urine
Identifiers
CAS number 183321-74-6 YesY
ATC code L01XE03
PubChem CID 176870
DrugBank DB00530
ChemSpider 154044 YesY
UNII J4T82NDH7E YesY
KEGG D07907 YesY
ChEBI CHEBI:114785 YesY
ChEMBL CHEMBL553 YesY
Chemical data
Formula C22H23N3O4 
Mol. mass 393.436 g/mol
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Erlotinib hydrochloride (trade name Tarceva) is a drug used to treat non-small cell lung cancer (NSCLC), pancreatic cancer and several other types of cancer. It is a reversible tyrosine kinase inhibitor, which acts on the epidermal growth factor receptor (EGFR). It is marketed in the United States by Genentech and OSI Pharmaceuticals and elsewhere by Roche.