Axitinib

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

Description:Axitinib, also known as AG013736, is an orally bioavailable tyrosine kinase inhibitor. Axitinib inhibits the proangiogenic cytokines vascular endothelial growth factor (VEGF) and platelet-derived growth factor receptor (PDGF), thereby exerting an anti-angiogenic effect. A xitinib has received FDA (27 January 2012), EMA (13 September 2012), MHRA (3 September 2012) and TGA (26 July 2012) approval for use as a treatment for renal cell carcinoma.

Price and Availability

Axitinib, purity > 98%, is in stock. The same day shipping out after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 200400Name: AxitinibCAS#: 319460-85-0Chemical Formula: C22H18N4OSExact Mass: 386.12013Molecular Weight: 386.47Elemental Analysis:C, 68.37; H, 4.69; N, 14.50; O, 4.14; S, 8.30

Synonym:AG013736; AG 013736; AG-013736; Axitinib; Brand name: Inlyta.

IUPAC/Chemical Name:(E)-N-methyl-2-((3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-yl)thio)benzamide

InChi Key:RITAVMQDGBJQJZ-FMIVXFBMSA-N

InChi Code:InChI=1S/C22H18N4OS/c1-23-22(27)18-7-2-3-8-21(18)28-16-10-11-17-19(25-26-20(17)14-16)12-9-15-6-4-5-13-24-15/h2-14H,1H3,(H,23,27)(H,25,26)/b12-9+

SMILES Code:O=C(NC)C1=CC=CC=C1SC2=CC3=C(C=C2)C(/C=C/C4=NC=CC=C4)=NN3

Technical Data

Additional Information

Axitinib (also known as AG013736) is a small molecule tyrosine kinase inhibitor under development by Pfizer. It inhibits multiple targets, including VEGFR-1, VEGFR-2, VEGFR-3, platelet derived growth factor receptor (PDGFR), and cKIT (CD117). It has been shown to significantly inhibit growth of breast cancer in xenograft models  and has been successful in trials with renal cell carcinoma (RCC)  and several other tumor types.Axitinib is a white to light-yellow powder with a pKa of 4.8. The solubility of axitinib in aqueous media over the range pH 1.1 to pH 7.8 is in excess of 0.2 μg/mL. The partition coefficient (n-octanol/water) is 3.5.  A Phase II clinical trial showed good response in combination chemotherapy with Gemcitabine for advanced pancreatic cancer. However, Pfizer reported on January 30, 2009 that Phase III clinical trials of the drug when used in combination with Gemcitabine showed no evidence of improved survival rates over treatments using Gemcitabine alone for advanced pancreatic cancer and halted the trial.  see http://en.wikipedia.org/wiki/Axitinib.  

References

1: Gunnarsson O, Pfanzelter NR, Cohen RB, Keefe SM.Evaluating the safety and efficacy of axitinib in the treatment ofadvanced renal cell carcinoma. Cancer Manag Res. 2015 Feb 11;7:65-73.doi: 10.2147/CMAR.S74202. eCollection 2015. Review. PubMed PMID:25709499; PubMed Central PMCID: PMC4334173.

2: Tzogani K, Skibeli V, Westgaard I, Dalhus M, Thoresen H, Slot KB,Damkier P, Hofland K, Borregaard J, Ersbøll J, Salmonson T, Pieters R,Sylvester R, Mickisch G, Bergh J, Pignatti F. The European MedicinesAgency Approval of Axitinib (Inlyta) for the Treatment of Advanced RenalCell Carcinoma After Failure of Prior Treatment With Sunitinib or aCytokine: Summary of the Scientific Assessment of the Committee forMedicinal Products for Human Use. Oncologist. 2015 Feb;20(2):196-201.Epub 2015 Jan 23. Review. PubMed PMID: 25616431; PubMed Central PMCID:PMC4319625.

3: Borst DL, Arruda LS, MacLean E, Pithavala YK, Morgado JE. Commonquestions regarding clinical use of axitinib in advanced renal cellcarcinoma. Am J Health Syst Pharm. 2014 Jul 1;71(13):1092-6. doi:10.2146/ajhp130581. Review. PubMed PMID: 24939498.

4: Verzoni E, Grassi P, Testa I, Iacovelli R, Biondani P, Garanzini E,De Braud F, Procopio G. Targeted treatments in advanced renal cellcarcinoma: focus on axitinib. Pharmgenomics Pers Med. 2014 Mar27;7:107-16. doi: 10.2147/PGPM.S37098. eCollection 2014. Review. PubMedPMID: 24715765; PubMed Central PMCID: PMC3977458.

5: Bracarda S, Castellano D, Procopio G, Sepúlveda JM, Sisani M, VerzoniE, Schmidinger M. Axitinib safety in metastatic renal cell carcinoma:suggestions for daily clinical practice based on case studies. ExpertOpin Drug Saf. 2014 Apr;13(4):497-510. doi:10.1517/14740338.2014.888413. Review. PubMed PMID: 24641566.

6: Akaza H, Fukuyama T. Axitinib for the treatment of advanced renalcell carcinoma. Expert Opin Pharmacother. 2014 Feb;15(2):283-97. doi:10.1517/14656566.2014.868436. Epub 2013 Dec 13. Review. PubMed PMID:24328549.

7: Gross-Goupil M, François L, Quivy A, Ravaud A. Axitinib: a review ofits safety and efficacy in the treatment of adults with advanced renalcell carcinoma. Clin Med Insights Oncol. 2013 Oct 29;7:269-77. doi:10.4137/CMO.S10594. Review. PubMed PMID: 24250243; PubMed Central PMCID:PMC3825605.

8: Chen Y, Tortorici MA, Garrett M, Hee B, Klamerus KJ, Pithavala YK.Clinical pharmacology of axitinib. Clin Pharmacokinet. 2013Sep;52(9):713-25. doi: 10.1007/s40262-013-0068-3. Review. PubMed PMID:23677771.

9: Qi WX, He AN, Shen Z, Yao Y. Incidence and risk of hypertension witha novel multi-targeted kinase inhibitor axitinib in cancer patients: asystematic review and meta-analysis. Br J Clin Pharmacol. 2013Sep;76(3):348-57. doi: 10.1111/bcp.12149. Review. PubMed PMID: 23617405;PubMed Central PMCID: PMC3769663.

10: King JW, Lee SM. Axitinib for the treatment of advancednon-small-cell lung cancer. Expert Opin Investig Drugs. 2013Jun;22(6):765-73. doi: 10.1517/13543784.2013.775243. Epub 2013 Mar 1.Review. PubMed PMID: 23452008.