semaxanib   Click here for help

GtoPdb Ligand ID: 5056

Synonyms: SU 5416 | SU5416 | VEGF receptor 2 kinase inhibitor III
PDB Ligand
Compound class: Synthetic organic
Comment: Semaxanib was a precursor in the development of the next generation kinase inhibitor ultimately approved as sunitinib.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 44.89
Molecular weight 238.11
XLogP 2.33
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES O=C1Nc2c(C1=Cc1[nH]c(cc1C)C)cccc2
Isomeric SMILES O=C1Nc2c(/C/1=C/c1[nH]c(cc1C)C)cccc2
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-
No information available.
Summary of Clinical Use Click here for help
A Phase 2 clinical trial (NCT00009919) investigating semaxanib as a therapy for metastatic kidney cancer was terminated. A single Phase 2I trial for advanced colorectal cancer (NCT00004252) was completed, but further development of the compound was ceased in light of the advances made towards next-generation kinase inhibitors with significantly improved efficacy.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Semaxanib targets the VEGF angiogenic pathway by inhibiting endothelial VEGFR1 and VEGFR2 (aka KDR) [2]. This inhibits solid tumour growth by blocking the creation of the new vasculature essential for tumour expansion [2].