izencitinib   Click here for help

GtoPdb Ligand ID: 10458

Synonyms: example 1 [WO2016191524A1] | JNJ-8398 | JNJ8398 | TD-1473 | TD1473
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Izencitinib (TD-1473) is described as a Janus kinase (JAK) inhibitor in INN proposed list 121 (of August 2019). It is example 1 in Theravance Biopharma's patent that claims JAK inhibitors for immunomodulatory potential [1]. Despite this 2020 article that describes preclinical development and early clinical evaluation of TD-1473 [2], the chemical structure remains undisclosed. TD-1473 is orally delivered, and was designed to be gut-selective in its action, for application in inflammatory bowel diseases.
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 7
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 105.55
Molecular weight 402.23
XLogP 3.15
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES N#CCCN1C2CCC1CC(C2)Nc1nc(Nc2n[nH]c(c2)C)cc2c1cccn2
Isomeric SMILES N#CCCN1[C@@H]2CC[C@H]1CC(C2)Nc1nc(Nc2n[nH]c(c2)C)cc2c1cccn2
InChI InChI=1S/C22H26N8/c1-14-10-21(29-28-14)26-20-13-19-18(4-2-8-24-19)22(27-20)25-15-11-16-5-6-17(12-15)30(16)9-3-7-23/h2,4,8,10,13,15-17H,3,5-6,9,11-12H2,1H3,(H3,25,26,27,28,29)/t15?,16-,17+
Immunopharmacology Comments
TD-1473 is a pan-JAK inhibitor with immunomodulatory potential [1]. It is intended to inhibit proinflammatory cytokine signalling selectively within the gastrointestinal tract, with limited systemic exposure [2].