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Merck
CN

PZ0193

Axitinib

≥98% (HPLC), powder, tyrosine kinase inhibitor

Synonym(s):

AG-013736, N-Methyl-2-((3-((1E)-2-(pyridin-2-yl)ethenyl)-1H-indazol-6-yl)sulfanyl)benzamide

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About This Item

Empirical Formula (Hill Notation):
C22H18N4OS
CAS Number:
319460-85-0
Molecular Weight:
386.47
UNSPSC Code:
51111800
PubChem Substance ID:
329823767
NACRES:
NA.77
MDL number:
MFCD09837898

Key Documents

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Product Name

Axitinib, ≥98% (HPLC)

SMILES string

CNC(=O)c1ccccc1Sc2ccc3c(\C=C\c4ccccn4)n[nH]c3c2

InChI key

RITAVMQDGBJQJZ-FMIVXFBMSA-N

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+

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥8 mg/mL

storage temp.

room temp

Quality Level

100

Gene Information

human ... FLT1(2321), FLT4(2324), KDR(3791)

Application

Axitinib has been used as a vascular endothelial growth factor (VEGF) receptor tyrosine kinase inhibitor (TKI) to study its effect on renal cancer cell proliferation in vitro. It has also been used to inhibit anterior mesenteric artery (AMA) angiogenesis in dechlorinated embryos maintained in conditioned water (CW).

Biochem/physiol Actions

Axitinib (AG-013736) is an orally available, potent (picomolar) and selective tyrosine kinase inhibitor that blocks VEGF receptors 1, 2 and 3. The drug blocks VEGF-mediated endothelial cell survival, tube formation, and downstream signaling through endothelial nitric oxide synthase, Akt and extracellular signal-regulated kinase.
Orally available, potent and selective inhibitor of VEGF receptors 1, 2 and 3

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H302,H400

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000340109
0000340109
0000188349
091M4705V
0000188349

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Hypoxic 3D in vitro culture models reveal distinct resistance processes to TKIs in renal cancer cells
Bielecka Z, et al.
Cell & Bioscience, 7(1), 71-71 (2017)
Ana Carolina Monteiro et al.
Molecular oncology, 13(6), 1433-1449 (2019-05-10)
The high mortality rate of melanoma is broadly associated with its metastatic potential. Tumor cell dissemination is strictly dependent on vascularization; therefore, angiogenesis and lymphangiogenesis play an essential role in metastasis. Hence, a better understanding of the players of tumor
Renin expression in developing zebrafish is associated with angiogenesis and requires the Notch pathway and endothelium
Rider S, et al.
American Journal of Physiology: Renal Physiology, 309(6), F531-F539 (2015)
Fatma Demircan Yildirim et al.
Medycyna pracy, 71(6), 649-663 (2020-10-28)
About 8 million healthcare workers in the USA are potentially exposed to hazardous drugs or their toxic metabolites over a long period of time despite the fact that both the Occupational Safety and Health Administration and the European Parliament recommend
Decreased efficacy of drugs targeting the vascular endothelial growth factor pathway by the epigenetic silencing of FLT1 in renal cancer cells
Kim JY, et al.
Clinical epigenetics, 7(1), 99-99 (2015)
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