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.
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2D Structure
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Physico-chemical Properties
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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
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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+
No information available.
Summary of Clinical Use Click here for help
Izencitinib (TD-1473) was progressed to clinical evaluation to determine safety and efficacy as a therapy for inflammatory bowel diseases. As of August 2021, clinical outcomes had failed to meet expectations in Crohn's disease or ulcerative colitis.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03920254 TD-1473 Long-Term Safety (LTS) Ulcerative Colitis (UC) Study Phase 2/Phase 3 Interventional Theravance Biopharma
NCT03758443 Efficacy & Safety of TD-1473 in Ulcerative Colitis Phase 2/Phase 3 Interventional Theravance Biopharma