nintedanib   Click here for help

GtoPdb Ligand ID: 5936

Synonyms: BIBF-1120 | BIBF1120 | Ofev® | Vargatef®
Approved drug PDB Ligand
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).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: nintedanib

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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-
No information available.
Summary of Clinical Use Click here for help
Nintedanib was originally approved as a treatment for idiopathic pulmonary fibrosis. Subsequently it has been approved (by the FDA) to slow pulmonary fuction decline in patients with systemic sclerosis-associated interstitial lung diseases (ILD).
Click here to link to current list of nintedanib studies.
In October 2019 the FDA granted Breakthrough Therapy Designation to nintedanib for the treatment of progressive chronic fibrosing ILD, based on preliminary results from the Phase 3 INBUILD trial (NCT02999178). This resulted in full approval for this indication in March 2020.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Nintedanib inhibits multiple angiogenic pathways, and appears to also inhibit pathways associated with the fibrotic scarring of the lung observed in idiopathic pulmonary fibrosis (IPF). In tumours inhibition of VEGF receptor (VEGFR), PDGFR and FGFR kinase activity reduces tumour angiogenesis/neo-vascularisation, thereby restricitng tumour expansion [2]. The mechanism in IPF is less clear. See [1] and [3] for further information.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02999178 Efficacy and Safety of Nintedanib in Patients With Progressive Fibrosing Interstitial Lung Disease (PF-ILD) Phase 3 Interventional Boehringer Ingelheim
External links Click here for help