eganelisib   Click here for help

GtoPdb Ligand ID: 9563

Synonyms: compound 26 [PMID: 27660692] | IPI-549 | IPI549
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Eganelisib (IPI549) is an orally bioavailable, highly selective small molecule PI3Kγ inhibitor [1].
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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

eganelisib 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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 7
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 124.61
Molecular weight 528.2
XLogP 5.31
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Cn1ncc(c1)C#Cc1cccc2c1c(=O)n(c(c2)C(NC(=O)c1c(N)nn2c1nccc2)C)c1ccccc1
Isomeric SMILES Cn1ncc(c1)C#Cc1cccc2c1c(=O)n(c(c2)[C@@H](NC(=O)c1c(N)nn2c1nccc2)C)c1ccccc1
InChI InChI=1S/C30H24N8O2/c1-19(34-29(39)26-27(31)35-37-15-7-14-32-28(26)37)24-16-22-9-6-8-21(13-12-20-17-33-36(2)18-20)25(22)30(40)38(24)23-10-4-3-5-11-23/h3-11,14-19H,1-2H3,(H2,31,35)(H,34,39)/t19-/m0/s1
InChI Key XUMALORDVCFWKV-IBGZPJMESA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
IPI-549 has been advanced to phase 2 clinical evaluations, either as monotherapy or in combination with chemotherapy drugs and/or immuno-oncology agents (e.g. the anti-PD-1 checkpoint inhibitor nivolumab).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02637531 A Dose-Escalation Study to Evaluate the Safety, Tolerability, Pharmacokinetics, and Pharmacodynamics of IPI-549 Phase 1 Interventional Infinity Pharmaceuticals, Inc. This trial is known as the MARIO-1 study.
NCT03980041 Study to Evaluate the Efficacy/Safety of IPI-549 in Combination With Nivolumab in Patients With Advanced Urothelial Carcinoma (MARIO-275) Phase 2 Interventional Infinity Pharmaceuticals, Inc. Known as the MARIO-275 (MAcrophage Reprogramming in Immuno-Oncology) study, this is a global, randomized, controlled combination trial of eganelisib combined with in immuno-oncology therapy naïve urothelial cancer.
NCT03961698 Evaluation of IPI-549 Combined With Front-line Treatments in Pts. With Triple-Negative Breast Cancer or Renal Cell Carcinoma (MARIO-3) Phase 2 Interventional Infinity Pharmaceuticals, Inc. Known as the MARIO-3 study, this is the first eganelisib combination trial in front-line advanced cancer patients. It will evaluate IPI549 (eganelisib) in combination with and in front-line triple-negative breast cancer (TNBC) and in combination with and in front-line renal cell carcinoma (RCC).