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).
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2D Structure
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Physico-chemical Properties
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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
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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
References
1. Dimitroulis IA. (2014)
Nintedanib: a novel therapeutic approach for idiopathic pulmonary fibrosis.
Respir Care, 59 (9): 1450-5. [PMID:24782550]
2. Hilberg F, Roth GJ, Krssak M, Kautschitsch S, Sommergruber W, Tontsch-Grunt U, Garin-Chesa P, Bader G, Zoephel A, Quant J et al.. (2008)
BIBF 1120: triple angiokinase inhibitor with sustained receptor blockade and good antitumor efficacy.
Cancer Res, 68 (12): 4774-82. [PMID:18559524]
3. Hunninghake GM. (2014)
A new hope for idiopathic pulmonary fibrosis.
N Engl J Med, 370 (22): 2142-3. [PMID:24836311]
4. Stopfer P, Rathgen K, Bischoff D, Lüdtke S, Marzin K, Kaiser R, Wagner K, Ebner T. (2011)
Pharmacokinetics and metabolism of BIBF 1120 after oral dosing to healthy male volunteers.
Xenobiotica, 41 (4): 297-311. [PMID:21204634]