Axitinib , ≥99% , 319460-85-0

Synonym(s):
AG-013736;N-Methyl-2-((3-((1E)-2-(pyridin-2-yl)ethenyl)-1H-indazol-6-yl)sulfanyl)benzamide

CAS NO.：319460-85-0

Empirical Formula: C22H18N4OS

Molecular Weight: 386.47

MDL number: MFCD09837898

EINECS: 638-771-6

PRODUCT Properties

• Melting point: 213-215°C
• Boiling point: 668.9±55.0 °C(Predicted)
• Density: 1.4
• storage temp.: room temp
• solubility: DMSO: ≥8mg/mL
• form: powder
• pka: 12.70±0.40(Predicted)
• color: white to tan
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• InChI: 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+
• InChIKey: RITAVMQDGBJQJZ-FMIVXFBMSA-N
• SMILES: C(NC)(=O)C1=CC=CC=C1SC1=CC2=C(C=C1)C(/C=C/C1=NC=CC=C1)=NN2

Description and Uses

In January 2012, the US FDA approved axitinib (also referred to as AG-013736) for the treatment of advanced renal cell carcinoma (RCC) for patients who have not responded to prior therapy. Axitinib is a pan VEGF inhibitor and functions by binding to the intracellular tyrosine kinase catalytic domain of VEGF leading to blockade of signaling through this angiogenic pathway. Axitinib is50–400 times more potent for VEGF (enzyme Ki and cellular IC_50s for VEGF 1, 2, and 3 are ～0.1 nM) than first-generation inhibitors like sorafenib and sunitinib. Axitinib also inhibits c-Kit and PDGFR(α/β) with enzyme Ki's of ～2 nM and was selective when tested against a broad panel of other protein kinases. Axitinib was discovered by a structure-based drug design approach and binds to the kinase domain of VEGF in a DFG-out conformation. Axitinib blocks VEGF-2 phosphorylation up to 7 h postdose in vivo and inhibits endothelial cell proliferation in xenograft tumors implanted in mice. Synthetic routes to axitinib employing a Migita coupling to form the diaryl sulfide and a Heck reaction to install the 2-styrylpyridine moiety have been reported.

Axitinib is a tyrosine kinase inhibitor. Axitinib is used in cancer therapy.

Safety

• Symbol(GHS): GHS07,GHS09
• Signal word: Warning
• Hazard statements: H302-H400
• Precautionary statements: P273-P301+P312+P330
• Hazard Codes: Xn,N
• Risk Statements: 22-50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• HS Code: 29333990