10249. Vandetanib

Nomenclature

CAS number: 443913-73-3
N-(4-Bromo-2-fluorophenyl)-6-methoxy-7-[(1-methyl-4-piperidinyl)methoxy]-4-quinazolinamine; 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline; N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazolin-4-amine; ZD-6474; Zactima (AstraZeneca).
C22H24BrFN4O2; mol wt 475.35.
C 55.59%, H 5.09%, Br 16.81%, F 4.00%, N 11.79%, O 6.73%.

Description and references

Inhibitor of VEGFR (vascular endothelial growth factor receptor) and EGFR (epidermal growth factor receptor) tyrosine kinases; inhibits angiogenesis. Prepn: L. F. A. Hennequin et al., WO 01032651; eidem, US 7173038 (2001, 2007 both to AstraZeneca); L. F. Hennequin et al., J. Med. Chem. 45 1300 (2002) DOI PubMed. Pharmacokinetics in cancer patients: S. N. Holden et al., Ann. Oncol. 16, 1391 (2005) DOI PubMed; K. D. Miller et al., Clin. Cancer Res. 11, 3369 (2005) DOI PubMed. Review of pharmacology: A. J. Ryan, S. R. Wedge, Br. J. Cancer 92, Suppl. 1, S6-S13 (2005) DOI; of development and clinical experience: R. S. Herbst et al., Expert Opin. Invest. Drugs 16, 239-249 (2007) DOI.

Chemical structure

Properties

Soly in water: 330 μM (pH 7.4); ≈650 μM (pH ≈6.5). Log P (octanol/water): 5.0.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Tyrosine Kinase Inhibitors