sunitinib   

GtoPdb Ligand ID: 5713

Synonyms: SU11248 | Sutent®
sunitinib is an approved drug (FDA and EMA (2006))
Compound class: Synthetic organic
Comment: Sunitinib is a Type-1 kinase inhibitor and was first approved by the US FDA and EMA in 2006.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 77.23
Molecular weight 398.21
XLogP 2.94
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCN(CCNC(=O)c1c(C)[nH]c(c1C)C=C1C(=O)Nc2c1cc(F)cc2)CC
Isomeric SMILES CCN(CCNC(=O)c1c(C)[nH]c(c1C)/C=C/1\C(=O)Nc2c1cc(F)cc2)CC
InChI InChI=1S/C22H27FN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12-
InChI Key WINHZLLDWRZWRT-ATVHPVEESA-N
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
KIT proto-oncogene, receptor tyrosine kinase Hs Inhibitor Inhibition 9.4 pKd - 2
pKd 9.4 (Kd 3.7x10-10 M) [2]
platelet derived growth factor receptor beta Hs Inhibitor Inhibition 8.1 pKi - 6
pKi 8.1 (Ki 8x10-9 M) [6]
fibroblast growth factor receptor 1 Hs Inhibitor Inhibition 6.1 pKi - 6
pKi 6.1 (Ki 8.3x10-7 M) [6]
ret proto-oncogene Hs Inhibitor Inhibition 8.8 pIC50 - 5
pIC50 8.8 (IC50 1.7x10-9 M) [5]
platelet derived growth factor receptor beta Hs Inhibitor Inhibition 8.2 pIC50 - 5
pIC50 8.2 (IC50 5.7x10-9 M) [5]
fms related receptor tyrosine kinase 3 Hs Inhibitor Inhibition 8.2 pIC50 - 4
pIC50 8.2 (IC50 6.5x10-9 M) [4]
fms related receptor tyrosine kinase 4 Hs Inhibitor Inhibition 8.1 pIC50 - 4
pIC50 8.1 (IC50 8.9x10-9 M) [4]
KIT proto-oncogene, receptor tyrosine kinase Hs Inhibitor Inhibition 7.9 pIC50 - 4
pIC50 7.9 (IC50 1.31x10-8 M) [4]
kinase insert domain receptor Hs Inhibitor Inhibition 7.7 pIC50 - 4
pIC50 7.7 (IC50 2.26x10-8 M) [4]
Ligand mentioned in the following text fields