nintedanib   

GtoPdb Ligand ID: 5936

Synonyms: BIBF-1120 | BIBF1120 | Ofev® | Vargatef®
nintedanib is an approved drug (FDA & EMA (2014))
Compound class: Synthetic organic
Comment: Nintedanib is a kinase inhibitor, targeting three arms of proangiogenic signalling via VEGFRs, PDGFR and FGFR [2]. It was developed by Boehringer Ingelheim.
Marketed formulations contain nintedanib esylate (PubChem CID 135476717).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 94.22
Molecular weight 539.25
XLogP 3.14
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COC(=O)c1ccc2c(c1)NC(=O)C2=C(c1ccccc1)Nc1ccc(cc1)N(C(=O)CN1CCN(CC1)C)C
Isomeric SMILES COC(=O)c1ccc2c(c1)NC(=O)/C/2=C(/c1ccccc1)\Nc1ccc(cc1)N(C(=O)CN1CCN(CC1)C)C
InChI InChI=1S/C31H33N5O4/c1-34-15-17-36(18-16-34)20-27(37)35(2)24-12-10-23(11-13-24)32-29(21-7-5-4-6-8-21)28-25-14-9-22(31(39)40-3)19-26(25)33-30(28)38/h4-14,19,32H,15-18,20H2,1-3H3,(H,33,38)/b29-28-
InChI Key XZXHXSATPCNXJR-ZIADKAODSA-N
Bioactivity Comments
Nintedanib is active in vivo, its effects observed as decreased vessel density and integrity and significant growth inhibition [2]. Nintedanib is rapidly metabolised to BIBF-1202 [4].
We have tagged FLT4 (VEGFR-3) as this drug's primary molecular target for data metrics purposes only. We fully acknowledge the multi-targeted nature of nintedanib and include reported kinase interactions in the table below.
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
fms related receptor tyrosine kinase 4 Hs Inhibitor Inhibition 7.9 pIC50 - 2
pIC50 7.9 (IC50 1.3x10-8 M) [2]
kinase insert domain receptor Hs Inhibitor Inhibition 7.7 pIC50 - 2
pIC50 7.7 (IC50 2.1x10-8 M) [2]
fms related receptor tyrosine kinase 1 Hs Inhibitor Inhibition 7.5 pIC50 - 2
pIC50 7.5 (IC50 3.1x10-8 M) [2]
fibroblast growth factor receptor 2 Hs Inhibitor Inhibition 7.4 pIC50 - 2
pIC50 7.4 (IC50 3.7x10-8 M) [2]
platelet derived growth factor receptor alpha Hs Inhibitor Inhibition 7.2 pIC50 - 2
pIC50 7.2 (IC50 5.9x10-8 M) [2]
platelet derived growth factor receptor beta Hs Inhibitor Inhibition 7.2 pIC50 - 2
pIC50 7.2 (IC50 6.5x10-8 M) [2]
fibroblast growth factor receptor 1 Hs Inhibitor Inhibition 7.2 pIC50 - 2
pIC50 7.2 (IC50 6.9x10-8 M) [2]
fibroblast growth factor receptor 3 Hs Inhibitor Inhibition 7.0 pIC50 - 2
pIC50 7.0 (IC50 1.08x10-7 M) [2]
fibroblast growth factor receptor 4 Hs Inhibitor Inhibition 6.2 pIC50 - 2
pIC50 6.2 (IC50 6.1x10-7 M) [2]