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
Click here for structure editor
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
References
1. Ito M, Yamazaki S, Yamagami K, Kuno M, Morita Y, Okuma K, Nakamura K, Chida N, Inami M, Inoue T et al.. (2017)
A novel JAK inhibitor, peficitinib, demonstrates potent efficacy in a rat adjuvant-induced arthritis model.
J. Pharmacol. Sci., 133 (1): 25-33. [PMID:28117214]
2. Oda K, Nakada N, Nagasaka Y. (2015)
In vitro/in vivo investigations to examine the gender differences in the pharmacokinetics of novel oral Janus kinase (JAK) inhibitor ASP015K and sulfate metabolite M2 in rats.
Xenobiotica, 45 (6): 488-94. [PMID:25539455]
3. Papp K, Pariser D, Catlin M, Wierz G, Ball G, Akinlade B, Zeiher B, Krueger JG. (2015)
A phase 2a randomized, double-blind, placebo-controlled, sequential dose-escalation study to evaluate the efficacy and safety of ASP015K, a novel Janus kinase inhibitor, in patients with moderate-to-severe psoriasis.
Br. J. Dermatol., 173 (3): 767-76. [PMID:25704750]