idelalisib   Click here for help

GtoPdb Ligand ID: 6741

Synonyms: CAL-101/CAL101 | GS-1101 | Zydelig®
Approved drug PDB Ligand Immunopharmacology Ligand
idelalisib is an approved drug (FDA & EMA (2014))
Compound class: Synthetic organic
Comment: Idelalisib is highly selective and potent oral inhibitor of phosphoinositide 3-kinase (PI3K) δ.
Click here for help

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.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: idelalisib

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 100.86
Molecular weight 415.16
XLogP 4.11
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES CCC(c1nc2cccc(c2c(=O)n1c1ccccc1)F)Nc1ncnc2c1[nH]cn2
Isomeric SMILES CC[C@@H](c1nc2cccc(c2c(=O)n1c1ccccc1)F)Nc1ncnc2c1[nH]cn2
InChI InChI=1S/C22H18FN7O/c1-2-15(28-20-18-19(25-11-24-18)26-12-27-20)21-29-16-10-6-9-14(23)17(16)22(31)30(21)13-7-4-3-5-8-13/h3-12,15H,2H2,1H3,(H2,24,25,26,27,28)/t15-/m0/s1
InChI Key IFSDAJWBUCMOAH-HNNXBMFYSA-N
No information available.
Summary of Clinical Use Click here for help
Idelalisib is a treatmet for difficult to treat leukemia and lymphomas. The potential of this drug was highlighted by the early termination of a phase 3 clinical trial, so that all participants could be given the drug [1]. Idelalisib was approved in July 2014, for patients with relapsed chronic lymphocytic leukemia (CLL), in combination with rituximab. The FDA also granted the drug accelerated approval for the treatment of patients with relapsed follicular B-cell non-Hodgkin lymphoma (FL) and relapsed small lymphocytic lymphoma (SLL), particularly indicated for patients who have received at least two prior systemic therapies.

To view a full list of trials registered with ClinicalTrials.gov assessing idelalisib, click here.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
PI3Kδ signaling is critical for the activation, proliferation, survival and trafficking of B lymphocytes and is hyperactive in many B-cell malignancies. Idelalisib inhibits this activity, ultimately leading to death of cancer cells.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)