Vandetanib(ZD6474)

Modify Date: 2024-01-02 15:59:22

Vandetanib(ZD6474) Structure
Vandetanib(ZD6474) structure
 Common Name Vandetanib(ZD6474)
CAS Number 443913-73-3 Molecular Weight 475.354
Density 1.4±0.1 g/cm3 Boiling Point 538.2±50.0 °C at 760 mmHg
Molecular Formula C22H24BrFN4O2 Melting Point 240-243ºC
MSDS N/A Flash Point 279.3±30.1 °C

 Use of Vandetanib(ZD6474)


Vandetanib is a potent inhibitor of VEGFR2 with an IC50 of 40 nM.

 Names

Name vandetanib
Synonym More Synonyms

 Vandetanib(ZD6474) Biological Activity

Description Vandetanib is a potent inhibitor of VEGFR2 with an IC50 of 40 nM.
Related Catalog
Target

VEGFR2:40 nM (IC50)

In Vitro Vandetanib inhibits VEGFR3 and EGFR with IC50 of 110 nM and 500 nM, respectively. Vandetanib is not sensitive to PDGFRβ, Flt1, Tie-2 and FGFR1 with IC50 of 1.1-3.6 μM, while almost has no activity against MEK, CDK2, c-Kit, erbB2, FAK, PDK1, Akt and IGF-1R with IC50 above 10 μM. Vandetanib inhibits VEGF-, EGF- and bFGF-stimulated HUVEC proliferation with IC50 of 60 nM, 170 nM and 800 nM, with no effect on basal endothelial cell growth. Vandetanib inhibits tumor cell growth with IC50 of 2.7 μM (A549) to 13.5 μM (Calu-6)[1]. Odanacatib is a weak inhibitor of antigen presentation, measured in a mouse B cell line (IC50=1.5±0.4 μM), compared to the Cat S inhibitor LHVS (IC50=0.001 μM) in the same assay. Odanacatib also shows weak inhibition of the processing of the MHC II invariant chain protein Iip10 in mouse splenocytes compared to LHVS (minimum inhibitory concentration 1-10 μM versus 0.01 μM, respectively)[2]. Vandetanib suppresses phosphorylation of VEGFR-2 in HUVECs and EGFR in hepatoma cells and inhibits cell proliferation[4].
In Vivo Vandetanib (15 mg/kg, p.o.) has a superior anti-tumor effect than gefitinib in the H1650 xenograft model, and suppresses tumor growth with IC50 of 3.5±1.2 μM[3]. In tumor-bearing mice, vandetanib (50 or 75 mg/kg) suppresses phosphorylation of VEGFR-2 and EGFR in tumor tissues, significantly reduces tumor vessel density, enhances tumor cell apoptosis, suppresses tumor growth, improves survival, reduces number of intrahepatic metastases, and upregulates VEGF, TGF-α, and EGF in tumor tissues[4].
Cell Assay Growth inhibition is measured by a modified MTT assay. Briefly, the cells are plated on 96-well plates at a density of 2000 cells per well and exposed to each gefitinib or vandetanib for 72 h. Each assay is performed in triplicate. The 50% inhibitory concentration (IC50) of each drug is determined as the mean±standard deviation (SD).
Animal Admin One million H1650 cells or H1650/PTEN cells (H1650 cells with a transfected PTEN gene) are injected subcutaneously into the backs of each mouse. On 10th day after injection, mice are randomLy assigned to three groups, which receive either vehicle, vandetanib (15 mg/kg/day), or gefitinib (15 mg/kg/day). Vehicle, vandetanib, and gefitinib are administered once per day p.o., five times per week. Tumor volume (width × width × length/2) and body weight are determined periodically. Tumor volumes are expressed as mean±SD. Differences in tumor volume are evaluated using Student's t-test.
References

[1]. Wedge SR, et al. ZD6474 inhibits vascular endothelial growth factor signaling, angiogenesis, and tumor growth following oral administration. Cancer Res. 2002 Aug 15;62(16):4645-55.

[2]. Hegedus C, et al. Interaction of the EGFR inhibitors gefitinib, vandetanib, pelitinib and neratinib with the ABCG2 multidrug transporter: implications for the emergence and reversal of cancer drug resistance. Biochem Pharmacol. 2012 Aug 1;84(3):260-7.

[3]. Takeda H, et al. Vandetanib is effective in EGFR-mutant lung cancer cells with PTEN deficiency. Exp Cell Res. 2013 Feb 15;319(4):417-23.

[4]. Inoue K, et al. Vandetanib, an inhibitor of VEGF receptor-2 and EGF receptor, suppresses tumor development and improves prognosis of liver cancer in mice. Clin Cancer Res. 2012 Jul 15;18(14):3924-33.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 538.2±50.0 °C at 760 mmHg
Melting Point 240-243ºC
Molecular Formula C22H24BrFN4O2
Molecular Weight 475.354
Flash Point 279.3±30.1 °C
Exact Mass 474.106659
PSA 59.51000
LogP 5.51
Vapour Pressure 0.0±1.4 mmHg at 25°C
Index of Refraction 1.629
Storage condition -20?C Freezer

 Safety Information

Hazard Codes Xi
Safety Phrases 24/25
HS Code 2933990090

 Synthetic Route

Formaldehyde structure

Formaldehyde

CAS#:50-00-0

N-DeMethyl Vandetanib structure

N-DeMethyl Vand...

CAS#:338992-12-4

~85%

Vandetanib(ZD6474) Structure

Vandetanib(ZD6474)

CAS#:443913-73-3

Literature: Gao, Mingzhang; Lola, Christian M.; Wang, Min; Miller, Kathy D.; Sledge, George W.; Zheng, Qi-Huang Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 11 p. 3222 - 3226
Formaldehyde structure

Formaldehyde

CAS#:50-00-0

TERT-BUTYL 4-(((4-((4-BROMO-2-FLUOROPHENYL)AMINO)-6-METHOXYQUINAZOLIN-7-YL)OXY)METHYL)PIPERIDINE-1-CARBOXYLATE structure

TERT-BUTYL 4-((...

CAS#:338992-20-4

~91%

Vandetanib(ZD6474) Structure

Vandetanib(ZD6474)

CAS#:443913-73-3

Literature: ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2007/36713 A2, 2007 ; Location in patent: Page/Page column 59; 60 ; WO 2007/036713 A2
4-Bromo-2-fluoroaniline structure

4-Bromo-2-fluor...

CAS#:367-24-8

4-chloro-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline structure

4-chloro-6-meth...

CAS#:264208-72-2

~91%

Vandetanib(ZD6474) Structure

Vandetanib(ZD6474)

CAS#:443913-73-3

Literature: Marzaro, Giovanni; Guiotto, Adriano; Pastorini, Giovanni; Chilin, Adriana Tetrahedron, 2010 , vol. 66, # 4 p. 962 - 968
4-Bromo-2-fluoroaniline structure

4-Bromo-2-fluor...

CAS#:367-24-8

~%

Vandetanib(ZD6474) Structure

Vandetanib(ZD6474)

CAS#:443913-73-3

Literature: Gao, Mingzhang; Lola, Christian M.; Wang, Min; Miller, Kathy D.; Sledge, George W.; Zheng, Qi-Huang Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 11 p. 3222 - 3226
7-(Benzyloxy)-4-chloro-6-methoxyquinazoline structure

7-(Benzyloxy)-4...

CAS#:162364-72-9

~%

Vandetanib(ZD6474) Structure

Vandetanib(ZD6474)

CAS#:443913-73-3

Literature: Gao, Mingzhang; Lola, Christian M.; Wang, Min; Miller, Kathy D.; Sledge, George W.; Zheng, Qi-Huang Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 11 p. 3222 - 3226
4-(4-bromo-2-fluorophenylamino)-6-methoxyquinazolin-7-ol structure

4-(4-bromo-2-fl...

CAS#:196603-96-0

~%

Vandetanib(ZD6474) Structure

Vandetanib(ZD6474)

CAS#:443913-73-3

Literature: Gao, Mingzhang; Lola, Christian M.; Wang, Min; Miller, Kathy D.; Sledge, George W.; Zheng, Qi-Huang Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 11 p. 3222 - 3226
7-(benzyloxy)-N-(4-bromo-2-fluorophenyl)-6-methoxyquinazolin-4-amine structure

7-(benzyloxy)-N...

CAS#:768350-54-5

~%

Vandetanib(ZD6474) Structure

Vandetanib(ZD6474)

CAS#:443913-73-3

Literature: Gao, Mingzhang; Lola, Christian M.; Wang, Min; Miller, Kathy D.; Sledge, George W.; Zheng, Qi-Huang Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 11 p. 3222 - 3226

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Synonyms

Vandetanib
4-Quinazolinamine, N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[(1-methyl-4-piperidinyl)methoxy]-
N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazolin-4-amine
ZACTIMA
ZD 6474
N-(4-Bromo-2-fluorophenyl)-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-amine
Caprelsa
ZD6474
N-(4-Bromo-2-fluorophenyl)-6-methoxy-7-[(1-methyl-4-piperidinyl)methoxy]-4-quinazolinamine
Vandetanib for research
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