Vandetanib Fumarate

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561181

CAS#: 338992-00-0 (free base)

Description: Vandetanib Fumarate is a once-daily orally available tyrosine kinase inhibitor that works by blocking RET (REarranged during Transfection), vascular endothelial growth factor receptor (VEGFR-2, VEGFR-3), and epidermal growth factor receptor and to a lesser extent VEGFR-1, which are important targets in thyroid cancer (TC). It is emerging as a potentially effective option in the treatment of advanced medullary thyroid cancer (MTC) and in dedifferentiated papillary thyroid cancer not responsive to radioiodine.


Price and Availability

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Vandetanib Fumarate is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 561181
Name: Vandetanib Fumarate
CAS#: 338992-00-0 (free base)
Chemical Formula: C26H28BrFN4O6
Exact Mass:
Molecular Weight: 591.4344
Elemental Analysis: C, 52.80; H, 4.77; Br, 13.51; F, 3.21; N, 9.47; O, 16.23


Synonym: Vandetanib Fumarate; Vandetanib; Caprelsa; HSDB 8198; Zactima; ZD 6474; ZD6474

IUPAC/Chemical Name: N-(4-Bromo-2-fluorophenyl)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazolin-4-amine Fumarate

InChi Key: NEJYMTWEAISFSJ-WLHGVMLRSA-N

InChi Code: InChI=1S/C22H24BrFN4O2.C4H4O4/c1-28-7-5-14(6-8-28)12-30-21-11-19-16(10-20(21)29-2)22(26-13-25-19)27-18-4-3-15(23)9-17(18)24;5-3(6)1-2-4(7)8/h3-4,9-11,13-14H,5-8,12H2,1-2H3,(H,25,26,27);1-2H,(H,5,6)(H,7,8)/b;2-1+

SMILES Code: CN1CCC(COC2=CC3=NC=NC(NC4=CC=C(Br)C=C4F)=C3C=C2OC)CC1.O=C(O)/C=C/C(O)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Fallahi P, Di Bari F, Ferrari SM, Spisni R, Materazzi G, Miccoli P, Benvenga S, Antonelli A. Selective use of vandetanib in the treatment of thyroid cancer. Drug Des Devel Ther. 2015 Jul 3;9:3459-70. doi: 10.2147/DDDT.S72495. eCollection 2015. Review. PubMed PMID: 26170630; PubMed Central PMCID: PMC4498730.

2: Cooper MR, Yi SY, Alghamdi W, Shaheen DJ, Steinberg M. Vandetanib for the treatment of medullary thyroid carcinoma. Ann Pharmacother. 2014 Mar;48(3):387-94. doi: 10.1177/1060028013512791. Epub 2013 Nov 14. Review. PubMed PMID: 24259657.

3: Fallahi P, Ferrari SM, Baldini E, Biricotti M, Ulisse S, Materazzi G, Miccoli P, Antonelli A. The safety and efficacy of vandetanib in the treatment of progressive medullary thyroid cancer. Expert Rev Anticancer Ther. 2016 Nov;16(11):1109-1118. Epub 2016 Sep 30. Review. PubMed PMID: 27650489.

4: De Luca A, D'Alessio A, Maiello MR, Gallo M, Bevilacqua S, Frezzetti D, Morabito A, Perrone F, Normanno N. Vandetanib as a potential treatment for breast cancer. Expert Opin Investig Drugs. 2014 Sep;23(9):1295-303. doi: 10.1517/13543784.2014.942034. Epub 2014 Aug 4. Review. PubMed PMID: 25089348.

5: Grande E, Kreissl MC, Filetti S, Newbold K, Reinisch W, Robert C, Schlumberger M, Tolstrup LK, Zamorano JL, Capdevila J. Vandetanib in advanced medullary thyroid cancer: review of adverse event management strategies. Adv Ther. 2013 Nov;30(11):945-66. doi: 10.1007/s12325-013-0069-5. Epub 2013 Nov 19. Review. PubMed PMID: 24249433; PubMed Central PMCID: PMC3898148.

6: Karras S, Anagnostis P, Krassas GE. Vandetanib for the treatment of thyroid cancer: an update. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):469-81. doi: 10.1517/17425255.2014.885015. Epub 2014 Feb 6. Review. PubMed PMID: 24502390.

7: Sim MW, Cohen MS. The discovery and development of vandetanib for the treatment of thyroid cancer. Expert Opin Drug Discov. 2014 Jan;9(1):105-14. doi: 10.1517/17460441.2014.866942. Epub 2013 Dec 4. Review. PubMed PMID: 24299515.

8: Ton GN, Banaszynski ME, Kolesar JM. Vandetanib: a novel targeted therapy for the treatment of metastatic or locally advanced medullary thyroid cancer. Am J Health Syst Pharm. 2013 May 15;70(10):849-55. doi: 10.2146/ajhp120253. Review. PubMed PMID: 23640345.

9: Tsang VH, Robinson BG, Learoyd DL. The safety of vandetanib for the treatment of thyroid cancer. Expert Opin Drug Saf. 2016 Aug;15(8):1107-13. doi: 10.1080/14740338.2016.1201060. Epub 2016 Jul 4. Review. PubMed PMID: 27301016.

10: Campbell MJ, Seib CD, Gosnell J. Vandetanib and the management of advanced medullary thyroid cancer. Curr Opin Oncol. 2013 Jan;25(1):39-43. doi: 10.1097/CCO.0b013e32835a42b9. Review. PubMed PMID: 23202050.

11: Chau NG, Haddad RI. Vandetanib for the treatment of medullary thyroid cancer. Clin Cancer Res. 2013 Feb 1;19(3):524-9. doi: 10.1158/1078-0432.CCR-12-2353. Epub 2012 Dec 11. Review. PubMed PMID: 23231950.

12: Chougnet CN, Schlumberger M, Leboulleux S, Baudin E. [Vandetanib, in the management of patients with locally advanced or metastatic medullary thyroid carcinomas]. Bull Cancer. 2014 Sep;101(9):891-5. doi: 10.1684/bdc.2014.2022. Review. French. PubMed PMID: 25296193.

13: Frampton JE. Vandetanib: in medullary thyroid cancer. Drugs. 2012 Jul 9;72(10):1423-36. doi: 10.2165/11209300-000000000-00000. Review. PubMed PMID: 22715896.

14: Grabowski P, Briest F, Baum RP, Zaknun JJ, Kulkarni HR, Zeitz M, Hörsch D. Vandetanib therapy in medullary thyroid cancer. Drugs Today (Barc). 2012 Nov;48(11):723-33. doi: 10.1358/dot.2012.48.11.1867323. Review. PubMed PMID: 23170308.

15: Vozniak JM, Jacobs JM. Vandetanib. J Adv Pract Oncol. 2012 Mar;3(2):112-6. Review. PubMed PMID: 25031937; PubMed Central PMCID: PMC4093302.

16: Qi WX, Shen Z, Lin F, Sun YJ, Min DL, Tang LN, He AN, Yao Y. Incidence and risk of hypertension with vandetanib in cancer patients: a systematic review and meta-analysis of clinical trials. Br J Clin Pharmacol. 2013 Apr;75(4):919-30. doi: 10.1111/j.1365-2125.2012.04417.x. Review. PubMed PMID: 22882307; PubMed Central PMCID: PMC3612709.

17: Durante C, Paciaroni A, Plasmati K, Trulli F, Filetti S. Vandetanib: opening a new treatment practice in advanced medullary thyroid carcinoma. Endocrine. 2013 Oct;44(2):334-42. doi: 10.1007/s12020-013-9943-9. Epub 2013 Apr 14. Review. PubMed PMID: 23584948.

18: Wong HL, de Boer RH. Vandetanib for the treatment of non-small-cell lung cancer. Expert Opin Pharmacother. 2011 Oct;12(14):2271-8. doi: 10.1517/14656566.2011.604634. Epub 2011 Aug 6. Review. PubMed PMID: 21819274.

19: Langmuir PB, Yver A. Vandetanib for the treatment of thyroid cancer. Clin Pharmacol Ther. 2012 Jan;91(1):71-80. doi: 10.1038/clpt.2011.272. Epub 2011 Dec 7. Review. PubMed PMID: 22158569.

20: Guo L, Tang J, Meng Q, Zhu Y, Xu L, Shi H, Liu Z. [Vandetanib treatment in refractory advanced lung adenocarcinoma patients: five cases and review of literature]. Zhongguo Fei Ai Za Zhi. 2012 Feb;15(2):122-6. doi: 10.3779/j.issn.1009-3419.2012.02.11. Review. Chinese. PubMed PMID: 22336242.