sunitinib   Click here for help

GtoPdb Ligand ID: 5713

Synonyms: SU11248 | Sutent®
Approved drug PDB Ligand
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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: sunitinib

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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 enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
large tumor suppressor kinase 2 Hs Inhibitor Inhibition 6.3 pKd - 8
pKd 6.3 (Kd 4.6x10-7 M) [8]
large tumor suppressor kinase 1 Hs Inhibitor Inhibition 6.2 pKd -
pKd 6.2 (Kd 6.3x10-7 M)
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 Primary target of this compound Hs Inhibitor Inhibition 9.4 pKd - 2
pKd 9.4 (Kd 3.7x10-10 M) [2]
platelet derived growth factor receptor beta Primary target of this compound 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 Primary target of this compound 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 Primary target of this compound Hs Inhibitor Inhibition 8.1 pIC50 - 4
pIC50 8.1 (IC50 8.9x10-9 M) [4]
KIT proto-oncogene, receptor tyrosine kinase Primary target of this compound 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