toceranib   Click here for help

GtoPdb Ligand ID: 11619

Synonyms: compound 12f [PMID: 12646019] | Palladiar® | PHA-291639 | PHA291639 | SU 11654 | SU-11654 | SU11654
PDB Ligand
Compound class: Synthetic organic
Comment: Toceranib (PHA-291639 and formerly SU11654) is a small molecule, multi-targeted receptor tyrosine kinase inhibitor [2]. It is structurally related to sunitinib. Targets include VEGFRs, FGFR, PDGFRs, and Kit (including constitutively active mutant forms [1]). Like sunitinib, toceranib has antiangiogenic and anitproliferative actions. Palladiar® branded toceranib is used to treat solid tumours in dogs.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 77.23
Molecular weight 396.2
XLogP 2.6
No. Lipinski's rules broken 0
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Canonical SMILES Fc1ccc2c(c1)/C(=C/c1[nH]c(c(c1C)C(=O)NCCN1CCCC1)C)/C(=O)N2
Isomeric SMILES Fc1ccc2c(c1)/C(=C/c1[nH]c(c(c1C)C(=O)NCCN1CCCC1)C)/C(=O)N2
InChI InChI=1S/C22H25FN4O2/c1-13-19(12-17-16-11-15(23)5-6-18(16)26-21(17)28)25-14(2)20(13)22(29)24-7-10-27-8-3-4-9-27/h5-6,11-12,25H,3-4,7-10H2,1-2H3,(H,24,29)(H,26,28)/b17-12-
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
platelet derived growth factor receptor alpha Hs Inhibitor Inhibition 8.3 pKi - 1
pKi 8.3 (Ki 5x10-9 M) [1]
kinase insert domain receptor Hs Inhibitor Inhibition 8.2 pKi - 1
pKi 8.2 (Ki 6x10-9 M) [1]
fibroblast growth factor receptor 1 Hs Inhibitor Inhibition 6.3 pKi - 1
pKi 6.3 (Ki 5x10-7 M) [1]