decernotinib   

GtoPdb Ligand ID: 8309

Synonyms: adelatinib | VRT-831509 | VX-509
Compound class: Synthetic organic
Comment: Decernotinib is a selective inhibitor of Janus kinase 3 (JAK3) [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 95.59
Molecular weight 392.16
XLogP 3.27
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCC(C(=O)NCC(F)(F)F)(Nc1ccnc(n1)c1c[nH]c2c1cccn2)C
Isomeric SMILES CC[C@](C(=O)NCC(F)(F)F)(Nc1ccnc(n1)c1c[nH]c2c1cccn2)C
InChI InChI=1S/C18H19F3N6O/c1-3-17(2,16(28)25-10-18(19,20)21)27-13-6-8-23-15(26-13)12-9-24-14-11(12)5-4-7-22-14/h4-9H,3,10H2,1-2H3,(H,22,24)(H,25,28)(H,23,26,27)/t17-/m1/s1
InChI Key ASUGUQWIHMTFJL-QGZVFWFLSA-N
No information available.
Summary of Clinical Use
Decernotinib reached Phase III clinical trial as a potential treatment for rheumatoid arthritis (RA), but development appears to have been terminated, apparently for strategic reasons.
Mechanism Of Action and Pharmacodynamic Effects
Inhibition of JAK3 mediates signalling via a small subset of cytokine receptors, with which JAK3 (and JAK1) associate. These include the receptors for IL-2, IL-4, IL-7, IL-9, IL-15 and IL-21 which share a common γ receptor chain. Partial or reversible inhibition of JAK3 provides effective modulation of the immune activity in conditions such as autoimmune disorders.