sorafenib   Click here for help

GtoPdb Ligand ID: 5711

Synonyms: BAY 43-9006 | Nexavar®
Approved drug PDB Ligand
sorafenib is an approved drug (FDA (2005), EMA (2006))
Compound class: Synthetic organic
Comment: Sorafenib is a broad spectrum Type-2 kinase inhibitor targeting VEGFR2, VEGFR3, PDGFRβ, Flt3, and KIT and non-receptor kinases RAF1 and BRAF [6].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 92.35
Molecular weight 464.09
XLogP 3.75
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNC(=O)c1nccc(c1)Oc1ccc(cc1)NC(=O)Nc1ccc(c(c1)C(F)(F)F)Cl
Isomeric SMILES CNC(=O)c1nccc(c1)Oc1ccc(cc1)NC(=O)Nc1ccc(c(c1)C(F)(F)F)Cl
InChI InChI=1S/C21H16ClF3N4O3/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,28,29,31)
InChI Key MLDQJTXFUGDVEO-UHFFFAOYSA-N
Bioactivity Comments
Sorafenib significantly inhibits neovascularization in xenograft models of human colon, breast, and non-small-cell lung cancer [6].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
cyclin dependent kinase 8 Hs Inhibitor Inhibition 7.0 pKd - 2
pKd 7.0 (Kd 9.96x10-8 M) [2]
Description: CDK8/cyclin C.
cyclin dependent kinase 19 Hs Inhibitor Inhibition 7.0 pKd - 2
pKd 7.0 (Kd 1.03x10-7 M) [2]
Description: CDK19/cyclin C.
Raf-1 proto-oncogene, serine/threonine kinase Hs Inhibitor Inhibition 8.2 pIC50 - 6
pIC50 8.2 (IC50 6x10-9 M) [6]
B-Raf proto-oncogene, serine/threonine kinase Hs Inhibitor Inhibition 7.7 pIC50 - 6
pIC50 7.7 (IC50 2.2x10-8 M) [6]
Selectivity at catalytic receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
kinase insert domain receptor Primary target of this compound Hs Inhibitor Inhibition 7.2 pKd - 3
pKd 7.2 (Kd 5.9x10-8 M) [3]
discoidin domain receptor tyrosine kinase 2 Hs Inhibitor Inhibition 8.0 pIC50 - 5
pIC50 8.0 (IC50 1x10-8 M) [5]
ret proto-oncogene Hs Inhibitor Inhibition 7.9 pIC50 - 5
pIC50 7.9 (IC50 1.4x10-8 M) [5]
fms related receptor tyrosine kinase 4 Mm Inhibitor Inhibition 7.7 pIC50 - 6
pIC50 7.7 (IC50 2x10-8 M) [6]
fms related receptor tyrosine kinase 3 Primary target of this compound Hs Inhibitor Inhibition 7.2 – 7.5 pIC50 - 6,8
pIC50 7.5 (IC50 3.3x10-8 M) [8]
pIC50 7.2 (IC50 5.8x10-8 M) [6]
platelet derived growth factor receptor beta Hs Inhibitor Inhibition 7.2 pIC50 - 8
pIC50 7.2 (IC50 5.7x10-8 M) [8]
platelet derived growth factor receptor beta Mm Inhibitor Inhibition 7.2 pIC50 - 6
pIC50 7.2 (IC50 5.7x10-8 M) [6]
KIT proto-oncogene, receptor tyrosine kinase Primary target of this compound Hs Inhibitor Inhibition 7.2 pIC50 - 6,8
pIC50 7.2 (IC50 6.8x10-8 M) [8]
pIC50 7.2 (IC50 6.8x10-8 M) [6]
kinase insert domain receptor Primary target of this compound Hs Inhibitor Inhibition 7.1 pIC50 - 6,8
pIC50 7.1 (IC50 9x10-8 M) [6]
pIC50 7.1 (IC50 9x10-8 M) [8]
fibroblast growth factor receptor 1 Hs Inhibitor Inhibition 6.2 pIC50 - 6,8
pIC50 6.2 (IC50 5.8x10-7 M) [8]
pIC50 6.2 (IC50 5.8x10-7 M) [6]
Ligand mentioned in the following text fields