edicotinib   Click here for help

GtoPdb Ligand ID: 8942

Synonyms: JNJ-40346527 | JNJ40346527 | US8497376, 15
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Edicotinib (PRV-6527; previously JNJ-40346527) was identified in a medicinal-chemistry lead optimization study to develop oral, selective CSF1R kinase inhibitors. The chemical structure is compound I-S in patent US20140045789 [2]. PubChem CID 25230468 is a tautomer which is also claimed in the patent.
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 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 103.69
Molecular weight 461.28
XLogP 4.84
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES N#Cc1c[nH]c(n1)C(=O)Nc1ccc(nc1C1=CCC(CC1)(C)C)C1CC(C)(C)OC(C1)(C)C
Isomeric SMILES N#Cc1c[nH]c(n1)C(=O)Nc1ccc(nc1C1=CCC(CC1)(C)C)C1CC(C)(C)OC(C1)(C)C
InChI InChI=1S/C27H35N5O2/c1-25(2)11-9-17(10-12-25)22-21(32-24(33)23-29-16-19(15-28)30-23)8-7-20(31-22)18-13-26(3,4)34-27(5,6)14-18/h7-9,16,18H,10-14H2,1-6H3,(H,29,30)(H,32,33)
No information available.
Summary of Clinical Use Click here for help
JNJ-40346527 has completed Phase 1/II clinical trial for relapsed or refractory Hodgkin's lymphoma (NCT01572519) and Phase 2 in patients with active rheumatoid arthritis (RA) who are not responding to current antirheumatic treatment (NCT01597739; results reported in [1]). Janssen terminated their development of JNJ-4034652 in 2014 due to a lack of efficacy. Subsequently, Provention Bio have tested PRV-6527 in Crohn's disease (see their Phase 2a PRINCE clinical trial NCT03854305; no results formally published as of October 2019).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
PRV-6527 inhibits CSF1R-mediated transformation of myeloid cells into inflammatory dendritic cells and macrophages, which are responsible for triggering pro-inflammatory processes in chronic inflammatory diseases such as rheumatoid arthritis and inflammatory bowel diseases.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01572519 A Study of JNJ-40346527 in Patients With Relapsed or Refractory Hodgkin Lymphoma Phase 1 Interventional Janssen Research & Development, LLC
NCT01597739 A Study of JNJ-40346527 in Patients With Active Rheumatoid Arthritis Despite Disease-modifying Antirheumatic Drug Therapy Phase 2 Interventional Janssen Research & Development, LLC
NCT03854305 Phase 2a Study of PRV-6527 in Subjects With Moderately to Severely Active Crohn's Disease Phase 2 Interventional Provention Bio, Inc.