Semaxanib (BAT-008962)
* For research use only

Semaxanib is a quinolone derivative with potential antineoplastic activity. Semaxanib reversibly inhibits ATP binding to the tyrosine kinase domain of vascular endothelial growth factor receptor 2 (VEGFR2), which may inhibit VEGF-stimulated endothelial cell migration and proliferation and reduce the tumor microvasculature. This agent also inhibits the phosphorylation of the stem cell factor receptor tyrosine kinase c-kit, often expressed in acute myelogenous leukemia cells.

Category
Others
Catalog number
BAT-008962
CAS number
204005-46-9
Molecular Formula
C15H14N2O
Molecular Weight
238.28
Semaxanib
Ordering Information
Catalog Number Size Price Stock Quantity
BAT-008962 100 mg $198 In stock
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IUPAC Name
(3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one
Synonyms
SU5416; SU-5416; SU 5416; Sugen 5416; semoxind
Appearance
Yellow to Orange Solid Powder
Purity
98%
Melting Point
>190ºC (dec.)
InChI
InChI=1S/C15H14N2O/c1-9-7-10(2)16-14(9)8-12-11-5-3-4-6-13(11)17-15(12)18/h3-8,16H,1-2H3,(H,17,18)/b12-8-
InChI Key
WUWDLXZGHZSWQZ-WQLSENKSSA-N
Canonical SMILES
CC1=CC(=C(N1)C=C2C3=CC=CC=C3NC2=O)C
1.A phase I dose escalation and pharmacodynamic study of SU5416 (semaxanib) combined with weekly cisplatin and irinotecan in patients with advanced solid tumors.
Martin LK1, Bekaii-Saab T, Serna D, Monk P, Clinton SK, Grever MR, Kraut EH. Onkologie. 2013;36(11):657-60. doi: 10.1159/000355665. Epub 2013 Oct 14.
BACKGROUND: This phase I study evaluated the safety of SU5416, a potent and selective inhibitor of the vascular endothelial growth factor (VEGF) receptor tyrosine kinase Flk-1, in combination with weekly cisplatin and irinotecan in patients with advanced solid tumors.
2.Photoinduced Isomerization and Hepatoxicities of Semaxanib, Sunitinib and Related 3-Substituted Indolin-2-ones.
Ngai MH1, So CL1, Sullivan MB2, Ho HK1, Chai CL3. ChemMedChem. 2016 Jan 5;11(1):72-80. doi: 10.1002/cmdc.201500475. Epub 2015 Nov 23.
3-Substituted indolin-2-ones are an important class of compounds that display a wide range of biological activities. Sunitinib is an orally available multiple tyrosine kinase inhibitor that has been approved by the US Food and Drug Administration (FDA) for the treatment of renal cell cancer. Sunitinib and a related compound, semaxanib, exist as thermodynamically stable Z isomers, which photoisomerize to E isomers in solution. In this study, 17 3-substituted indolin-2-ones were synthesized, and the kinetics of their photoisomerization were studied by (1)H NMR spectroscopy. The rate constants for photoisomerization ranged from 0.009 to 0.048 h(-1). Selected compounds were tested for cytotoxicity in the TAMH liver cell line. E/Z mixtures of four compounds were also assessed for toxicity in the TAMH and HepG2 cell lines. In some cases, the stereochemically pure drug was more toxic than the E/Z mixtures, but a general statement cannot be made.
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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