Vandetanib is a kind of small molecule multi-targeted tyrosine kinase inhibitor
Product Name: Vandetanib
Synonyms: VANDETANIB;4-Quinazolinamine, N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[(1-methyl-4-piperidinyl)methoxy]-;Vandetanib for research;4-(4-Bromo-2-fluoroanilino)-6-methoxy- 7-[(1-methylpiperidin-4-yl)methoxy]quinazoline;N-(4-Bromo-2-fluorophenyl)-6-methoxy-7-[(1-methyl-4-piperidinyl)methoxy]-4-quinazolinamine;Zactima;ZD 6474;7-((4-aminocyclohexyl)methoxy)-N-(4-bromo-2-fluorophenyl)-6-methoxyquinazolin-4-amine
Product Categories: Aromatics Compounds;Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Pharmaceutical intermediate;ZD6474
Mol File: 443913-73-3.mol
storage temp. -20?C Freezer
Usage And Synthesis
Vandetanib is a kind of small molecule multi-targeted tyrosine kinase inhibitor studied and developed by the British AstraZeneca Company. In April 2011, it was approved the US FDA for entering into market under the trade name Zactima. The drug, as a tablet, can be applied to the treatment of advanced medullary thyroid cancer of adult patients.
Vandetanib is a multi-targeted tyrosine kinase inhibitor, and belongs to the Anilinoquinazoline compounds, called “second generation Iressa”. It not only acts on the tumor cells, EGFR, VEGFR and RET tyrosine kinases, but can also inhibit other kind of tyrosine kinases and serine / threonine kinases. Vandetanib is the first approved drugs approved for treatment of medullary thyroid carcinoma. It is suitable for treating unresectable, locally advanced or metastatic-symptoms or progressive medullary thyroid carcinoma. A randomized, placebo-controlled clinical trial results have showed that vandetanib can significantly delay the progression time of locally advanced or metastatic medullary thyroid cancer. The recommended daily dose is 300 mg (oral), when the patient exhibits tolerance to drugs or being not able to tolerate the toxicity, they should stop treatment immediately. Those most common adverse reactions of this medicine include diarrhea, rash, acne, nausea, hypertension, headache, fatigue, loss of appetite and abdominal pain. The adverse reactions is dose-related; at <300 mg/d, the patient has a well tolerance with the maximum tolerated dose (MTD) being 300mg. There are many kinds disease types contained in the II phase clinical study. The NSCLC clinical trials of vandetanib are currently under way for our country.
(2).Treatment of advanced (non-small cell lung cancer) NSCLC
A study published in the [Journal of Clinical Oncology] have showed that compared with gefitinib which only has inhibitory effect on EGFR, vandetanib can effectively extend the progression-free survival period of the non-small cell lung cancer (NSCLC) patients.
In this phase II clinical trial conducted by doctors Ronald B. Natale from Los Angeles Cedars-Sinai Cancer Center, clinical study compared the treatment efficacy of vandetanib (300 mg/d) and gefitinib (250mg/d) on 168 cases of NSCLC patients who had been subject to failing first-line or second-line chemotherapy. Compared with gefitinib, vandetanib significantly increased efficiency and prolonged the progression-free survival, period respectively, by 8% and 1%, 11.9 weeks and 8.1 weeks, (P = 0.011). In clinical trials, if there is progression of the disease or if the patient can’t tolerate the toxicity, they allowed the patients to change the treatment regimen. Experimental results had shown that using gefitinib for replacing vandetanib in patients gave a disease control rate of 14% while using vandetanib to replace gefitinib gave a disease control rate of 32%. The overall survival period in the case of vandetanib → gefitinib was 6.1 months while it was 7.4 months in the cases of gefitinib → vandetanib.
(3).Vandetanib is a once-daily oral inhibitor of vascular endothelial growth factor receptor-2 and epidermal growth factor receptor kinase activity. The activity of Vandetanib plus Docetaxel was assessed in patients with previously treated non-small-cell lung cancer (NSCLC).
Use 4-hydroxy-3-methoxy-benzoic acid ethyl ester as a starting material, go through substitution, reduction, nitrification, reduction, cyclization aromatization to give 4-chloro-6-methoxy–7- (N- methyl piperidin-4-ylmethoxy) quinazoline (A), A was then reacted with 4-bromo-2-aniline to obtain the targeted compound vandetanib.
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