infigratinib   Click here for help

GtoPdb Ligand ID: 7877

Synonyms: BGJ 398 | BGJ-398 | BGJ398 | NVP-BGJ398 | Truseltiq®
Approved drug PDB Ligand
infigratinib is an approved drug (FDA (2021))
Compound class: Synthetic organic
Comment: The discovery and synthesis of infigratinib (BGJ-398) is described in [2], where it is compound 1h. It is an orally bioavailable, ATP-competitive pan inhibitor of human fibroblast growth factor receptors (FGFRs) with potential antiangiogenic and antineoplastic activities [2].
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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
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 8
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 95.09
Molecular weight 559.19
XLogP 4.47
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 CCN1CCN(CC1)c1ccc(cc1)Nc1ncnc(c1)N(C(=O)Nc1c(Cl)c(OC)cc(c1Cl)OC)C
Isomeric SMILES CCN1CCN(CC1)c1ccc(cc1)Nc1ncnc(c1)N(C(=O)Nc1c(Cl)c(OC)cc(c1Cl)OC)C
InChI InChI=1S/C26H31Cl2N7O3/c1-5-34-10-12-35(13-11-34)18-8-6-17(7-9-18)31-21-15-22(30-16-29-21)33(2)26(36)32-25-23(27)19(37-3)14-20(38-4)24(25)28/h6-9,14-16H,5,10-13H2,1-4H3,(H,32,36)(H,29,30,31)
InChI Key QADPYRIHXKWUSV-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
BGJ-398 (infigratinib) has been investigated in tumours that harbour FGFR mutations, including cholangiocarcinoma [1,5], urothelial carcinoma, and achondroplasia (which is commonly caused by activating mutations in FGFR3) [4]. Click here to link to ClinicalTrials.gov's complete listing of infigratinib trials. The EMA granted orphan drug designation in November 2020, for the treatment of cholangiocarcinoma.
The first FDA approval of infigratinib was as a treatment of FGFR2 gene fusion or rearrangement +ve cholangiocarcinoma, in May 2021. This approval was based on results from the phase 2 trial NCT02150967 [3].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
FGFRs are a family of receptor tyrosine kinases which may be upregulated in various tumor cell types and may be involved in tumor cell differentiation and proliferation, tumor angiogenesis, and tumor cell survival. Inhibition of these receptors may result in the inhibition of tumor angiogenesis and proliferation, and the induction of tumor cell death.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02150967 A Phase II, Single Arm Study of BGJ398 in Patients With Advanced Cholangiocarcinoma Phase 2 Interventional QED Therapeutics, Inc.