ZD4190 HCl

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

MedKoo CAT#: 206775

CAS#: 257938-36-6 (HCl)

Description: ZD-4190 is a potent VEGFR inhibitor. ZD4190 prevents tumour outgrowth in a model of minimal residual carcinoma in deep tissues.


Price and Availability

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ZD-4190 HCl 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#: 206775
Name: ZD4190 HCl
CAS#: 257938-36-6 (HCl)
Chemical Formula: C19H17BrClFN6O2
Exact Mass:
Molecular Weight: 495.7374
Elemental Analysis: C, 46.03; H, 3.46; Br, 16.12; Cl, 7.15; F, 3.83; N, 16.95; O, 6.45


Synonym: ZD-4190; ZD4190; ZD 4190; ZD-4190 HCl; ZD-4190 hydrochloride

IUPAC/Chemical Name: N-(4-Bromo-2-fluorophenyl)-7-[2-(1H-1,2,3-triazol-1-yl)ethoxy]-6-methoxyquinazoline-4-amine hydrochloride

InChi Key: IOFHDGSCWJNVRZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H16BrFN6O2.ClH/c1-28-17-9-13-16(10-18(17)29-7-6-27-5-4-24-26-27)22-11-23-19(13)25-15-3-2-12(20)8-14(15)21;/h2-5,8-11H,6-7H2,1H3,(H,22,23,25);1H

SMILES Code: COC1=CC2=C(NC3=CC=C(Br)C=C3F)N=CN=C2C=C1OCCN4N=NC=C4.[H]Cl


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: Yang M, Gao H, Yan Y, Sun X, Chen K, Quan Q, Lang L, Kiesewetter D, Niu G, Chen X. PET imaging of early response to the tyrosine kinase inhibitor ZD4190. Eur J Nucl Med Mol Imaging. 2011 Jul;38(7):1237-47. doi: 10.1007/s00259-011-1742-z. PubMed PMID: 21360246; PubMed Central PMCID: PMC3184245.

2: Gaballah K, Oakley R, Hills A, Ryan A, Partridge M. The antiangiogenic agent ZD4190 prevents tumour outgrowth in a model of minimal residual carcinoma in deep tissues. Br J Cancer. 2009 Aug 4;101(3):418-23. doi: 10.1038/sj.bjc.6605092. PubMed PMID: 19623179; PubMed Central PMCID: PMC2720249.

3: Nguyen QD, Rodrigues S, Rodrigue CM, Rivat C, Grijelmo C, Bruyneel E, Emami S, Attoub S, Gespach C. Inhibition of vascular endothelial growth factor (VEGF)-165 and semaphorin 3A-mediated cellular invasion and tumor growth by the VEGF signaling inhibitor ZD4190 in human colon cancer cells and xenografts. Mol Cancer Ther. 2006 Aug;5(8):2070-7. PubMed PMID: 16928828.

4: Checkley D, Tessier JJ, Wedge SR, Dukes M, Kendrew J, Curry B, Middleton B, Waterton JC. Dynamic contrast-enhanced MRI of vascular changes induced by the VEGF-signalling inhibitor ZD4190 in human tumour xenografts. Magn Reson Imaging. 2003 Jun;21(5):475-82. PubMed PMID: 12878256.

5: Pradel C, Siauve N, Bruneteau G, Clement O, de Bazelaire C, Frouin F, Wedge SR, Tessier JL, Robert PH, Frija G, Cuenod CA. Reduced capillary perfusion and permeability in human tumour xenografts treated with the VEGF signalling inhibitor ZD4190: an in vivo assessment using dynamic MR imaging and macromolecular contrast media. Magn Reson Imaging. 2003 Oct;21(8):845-51. PubMed PMID: 14599534.

6: Wedge SR, Ogilvie DJ, Dukes M, Kendrew J, Curwen JO, Hennequin LF, Thomas AP, Stokes ES, Curry B, Richmond GH, Wadsworth PF. ZD4190: an orally active inhibitor of vascular endothelial growth factor signaling with broad-spectrum antitumor efficacy. Cancer Res. 2000 Feb 15;60(4):970-5. PubMed PMID: 10706112.

7: Wedge SR, Ogilvie DJ. Inhibition of VEGF signal transduction. Identification of ZD4190. Adv Exp Med Biol. 2000;476:307-10. PubMed PMID: 10949675.

8: Morrison MS, Ricketts SA, Barnett J, Cuthbertson A, Tessier J, Wedge SR. Use of a novel Arg-Gly-Asp radioligand, 18F-AH111585, to determine changes in tumor vascularity after antitumor therapy. J Nucl Med. 2009 Jan;50(1):116-22. doi: 10.2967/jnumed.108.056077. PubMed PMID: 19091899.

9: Lloyd PG, Prior BM, Li H, Yang HT, Terjung RL. VEGF receptor antagonism blocks arteriogenesis, but only partially inhibits angiogenesis, in skeletal muscle of exercise-trained rats. Am J Physiol Heart Circ Physiol. 2005 Feb;288(2):H759-68. PubMed PMID: 15471974.

10: Brochot C, Bessoud B, Balvay D, Cuénod CA, Siauve N, Bois FY. Evaluation of antiangiogenic treatment effects on tumors' microcirculation by Bayesian physiological pharmacokinetic modeling and magnetic resonance imaging. Magn Reson Imaging. 2006 Oct;24(8):1059-67. PubMed PMID: 16997076.

11: Tazzyman S, Barry ST, Ashton S, Wood P, Blakey D, Lewis CE, Murdoch C. Inhibition of neutrophil infiltration into A549 lung tumors in vitro and in vivo using a CXCR2-specific antagonist is associated with reduced tumor growth. Int J Cancer. 2011 Aug 15;129(4):847-58. doi: 10.1002/ijc.25987. PubMed PMID: 21328342.

12: Clément O, Pradel C, Siauve N, Frouin F, Bruneteau G, Kahn E, Frija G, Cuénod CA. Assessing perfusion and capillary permeability changes induced by a VEGF inhibitor in human tumor xenografts using macromolecular MR imaging contrast media. Acad Radiol. 2002 Aug;9 Suppl 2:S328-9. PubMed PMID: 12188264.

13: Shepherd FA, Sridhar SS. Angiogenesis inhibitors under study for the treatment of lung cancer. Lung Cancer. 2003 Aug;41 Suppl 1:S63-72. Review. PubMed PMID: 12867064.

14: Sridhar SS, Shepherd FA. Targeting angiogenesis: a review of angiogenesis inhibitors in the treatment of lung cancer. Lung Cancer. 2003 Dec;42 Suppl 1:S81-91. Review. PubMed PMID: 14611919.

15: Hennequin LF, Stokes ES, Thomas AP, Johnstone C, Plé PA, Ogilvie DJ, Dukes M, Wedge SR, Kendrew J, Curwen JO. Novel 4-anilinoquinazolines with C-7 basic side chains: design and structure activity relationship of a series of potent, orally active, VEGF receptor tyrosine kinase inhibitors. J Med Chem. 2002 Mar 14;45(6):1300-12. PubMed PMID: 11881999.

16: Hartman GD, Fraley ME, Bilodeau MT. Kinase insert domain-containing receptor kinase inhibitors as anti-angiogenic agents. Expert Opin Investig Drugs. 2002 Jun;11(6):737-45. Review. PubMed PMID: 12036418.

17: Shepherd FA. Angiogenesis inhibitors in the treatment of lung cancer. Lung Cancer. 2001 Dec;34 Suppl 3:S81-9. Review. PubMed PMID: 11740999.

18: Klohs WD, Hamby JM. Antiangiogenic agents. Curr Opin Biotechnol. 1999 Dec;10(6):544-9. Review. PubMed PMID: 10600694.