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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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nintedanib is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA & EMA (2014))
IUPAC Name Click here for help
methyl (3Z)-3-[({4-[N-methyl-2-(4-methylpiperazin-1-yl)acetamido]phenyl}amino)(phenyl)methylidene]-2-oxo-2,3-dihydro-1H-indole-6-carboxylate
International Nonproprietary Names Click here for help
INN number INN
9229 nintedanib
Synonyms Click here for help
BIBF-1120 | BIBF1120 | Ofev® | Vargatef®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9616923
Reactome Reaction Reactome logo R-HSA-9674430, R-HSA-2077420, R-HSA-9674095
Other databases
CAS Registry No. 656247-17-5
ChEMBL Ligand CHEMBL502835
DrugCentral Ligand 4903
GtoPdb PubChem SID 178102559
PubChem CID 135423438
RCSB PDB Ligand XIN
Search Google for chemical match using the InChIKey XZXHXSATPCNXJR-ZIADKAODSA-N
Search Google for chemicals with the same backbone XZXHXSATPCNXJR
Search PubMed clinical trials nintedanib
Search PubMed titles nintedanib
Search PubMed titles/abstracts nintedanib
SynPHARM 79677 (in complex with kinase insert domain receptor)
UniChem Compound Search for chemical match using the InChIKey XZXHXSATPCNXJR-ZIADKAODSA-N
UniChem Connectivity Search for chemical match using the InChIKey XZXHXSATPCNXJR-ZIADKAODSA-N
Wikipedia Nintedanib

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Tocris
Nintedanib (links to external site)
Cat. No. 7049