izencitinib   Click here for help

GtoPdb Ligand ID: 10458

Synonyms: example 1 [WO2016191524A1]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Izencitinib (example 1 [WO2016191524A1]) 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]. Review of Theravance's disclosed pipeline reveals one JAK inhibitor coded TD-8326 in their asthma program. However, until the chemical structure of TD-8326 is formally disclosed its relationship to patent example 1 and izencitinib remains speculative.
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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
SMILES / InChI / InChIKey
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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+
InChI Key DADAEARVGOQWHV-ALOPSCKCSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
3-[(1R,5S)-3-[[7-[(5-methyl-1H-pyrazol-3-yl)amino]-1,6-naphthyridin-5-yl]amino]-8-azabicyclo[3.2.1]octan-8-yl]propanenitrile
International Nonproprietary Names Click here for help
INN number INN
11132 izencitinib
Synonyms Click here for help
example 1 [WO2016191524A1]
Database Links Click here for help
CAS Registry No. 2051918-33-1 (source: WHO INN record)
GtoPdb PubChem SID 385612218
PubChem CID 124090478
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