peficitinib   

GtoPdb Ligand ID: 8315

Synonyms: ASP015K | JNJ-54781532
Compound class: Synthetic organic
Comment: Peficitinib is a novel oral Janus kinase inhibitor [2] being investigated for potential anti-inflammatory action in autoimmune diseases including rheumatoid arthritis, psoriasis and ulcerative colitis.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 3
Topological polar surface area 104.03
Molecular weight 326.17
XLogP 1.83
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES NC(=O)c1cnc2c(c1NC1C3CC4CC1CC(C3)(C4)O)cc[nH]2
Isomeric SMILES NC(=O)c1cnc2c(c1NC1[C@@H]3CC4C[C@H]1CC(C3)(C4)O)cc[nH]2
InChI InChI=1S/C18H22N4O2/c19-16(23)13-8-21-17-12(1-2-20-17)15(13)22-14-10-3-9-4-11(14)7-18(24,5-9)6-10/h1-2,8-11,14,24H,3-7H2,(H2,19,23)(H2,20,21,22)/t9?,10-,11+,14?,18?
InChI Key DREIJXJRTLTGJC-JQCLMNFQSA-N
No information available.
Summary of Clinical Use
Peficitinib is being assessed in Phase III clinical trial as a potential treatment for rheumatoid arthritis (RA). A Phase IIa trial in patients with moderate to severe psoriasis has produced encouraging results [3].
Mechanism Of Action and Pharmacodynamic Effects
The Janus kinase (JAK) enzymes play a key role in cytokine signalling, which is involved in the pathological symptoms of immune-mediated disorders such as rheumatoid arthritis (RA). Peficitinib has been reported to inhinit all four JAKs at low nanomolar concentrations, although this data is not yet published in a peer reviewed article (see ASP015K: A Novel JAK Inhibitor Demonstrated Potent Efficacy in Adjuvant-Induced Arthritis Model in Rats, an abstract from the proceedings of the American College of Rheumatology/Association of Rheumatology Health Professionals, Annual Scientific Meeting, Washington DC, November 9-14, 2012).