nemiralisib   Click here for help

GtoPdb Ligand ID: 9425

Synonyms: compound 2 [PMID: 26301626] | GSK-2269557 | GSK2269557
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Nemiralisib (GSK2269557) is a PI3K inhibitor with selectivity for PI3Kδ over the other related isoforms [1]. The compound is active via inhalation and is being evaluated for its potential in respiratory inflammation. May be administered or used experimentally as the hydrochloride salt (PubChem CID 49784084). In the original study by Down et al. (2015) compound 3 (GSK2292767) was developed as a follow-up compound with reduced hERG activity and minimised systemic exposure [1].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 76.98
Molecular weight 440.23
XLogP 4.31
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CC(N1CCN(CC1)Cc1cnc(o1)c1cc(cc2c1cn[nH]2)c1cccc2c1cc[nH]2)C
Isomeric SMILES CC(N1CCN(CC1)Cc1cnc(o1)c1cc(cc2c1cn[nH]2)c1cccc2c1cc[nH]2)C
InChI InChI=1S/C26H28N6O/c1-17(2)32-10-8-31(9-11-32)16-19-14-28-26(33-19)22-12-18(13-25-23(22)15-29-30-25)20-4-3-5-24-21(20)6-7-27-24/h3-7,12-15,17,27H,8-11,16H2,1-2H3,(H,29,30)
Immunopharmacology Comments
Nemiralisib is being evaluated for immunomodulatory (anti-inflammatory) potential in clinical trials.
Immunopharmacology Disease
Disease X-Refs Comment References
Activated PI3K delta syndrome OMIM: 615513
Orphanet: ORPHA397596
Phase 2 clinical candidate for this condition (see NCT02593539). In the 2nd quarter of 2020, GSK made the decision to terminate the nemiralisib APDS programme, in a prioritisation review of their development pipeline.
Asthma Disease Ontology: DOID:2841
OMIM: 600807
Completed Phase 1 trial in asthma (see NCT01462617).
Chronic obstructive pulmonary disease Disease Ontology: DOID:3083
Phase 2 clinical candidate for COPD (see NCT02522299). 1