DEUCRAVACITINIB

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Synonyms
Status
Molecule Category UNKNOWN
UNII N0A21N6RAU

Structure

InChI Key BZZKEPGENYLQSC-UHFFFAOYSA-N
Smiles CNC(=O)c1nnc(NC(=O)C2CC2)cc1Nc1cccc(-c2ncn(C)n2)c1OC
InChI
InChI=1S/C20H22N8O3/c1-21-20(30)16-14(9-15(25-26-16)24-19(29)11-7-8-11)23-13-6-4-5-12(17(13)31-3)18-22-10-28(2)27-18/h4-6,9-11H,7-8H2,1-3H3,(H,21,30)(H2,23,24,25,29)

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H22N8O3
Molecular Weight 422.45
AlogP 1.73
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 7.0
Polar Surface Area 135.95
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 31.0

Bioactivity

Mechanism of Action Action Reference
Tyrosine-protein kinase TYK2 negative allosteric modulator NEGATIVE ALLOSTERIC MODULATOR Other
Protein: Tyrosine-protein kinase TYK2
Description: Non-receptor tyrosine-protein kinase TYK2
Organism : Homo sapiens
P29597 ENSG00000105397
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakA family
13 0-18 - 0-0 -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakB family
13 0-18 - 0-0 -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase STKR family TKL protein kinase STKR Type 2 subfamily
- 193 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- - - - 26
Assay Description Organism Bioactivity Reference
Inhibition of TYK2 in human Jurkat cells assessed as reduction in IFN-alpha stimulated TYK2 phosphorylation by caspase3/7 reagent-based Western blot analysis Homo sapiens 0.02 nM
Inhibition of JAK1/TYK2 in human Kit225 T cells assessed as inhibition of STAT phosphorylation by luciferase reporter assay Homo sapiens 5.0 nM
Inhibition of TYK2 in human whole blood assessed as decrease in IFNalpha-induced STAT5 phosphorylation preincubated for 1 hr followed by stimulation with IFN-alpha for 15 mins by fluorescence analysis Homo sapiens 13.0 nM
Inhibition of TYK2 in mouse whole blood assessed as decrease in IFNalpha-induced STAT1 phosphorylation preincubated for 1 hr followed by stimulation with IFN-alpha for 15 mins by fluorescence analysis Mus musculus 100.0 nM
Inhibition of TYK2 in human PBMC assessed as decrease in IFNalpha-induced STAT5 phosphorylation in CD3+ T cells preincubated for 1 hr followed by stimulation with IFN-alpha for 15 mins by flow cytometry Homo sapiens 2.0 nM
Inhibition of TYK2 in human PBMC assessed as decrease in IL23-induced STAT3 phosphorylation in CD161+/CD3+ T cells preincubated for 1 hr followed by stimulation with IL-23 for 15 mins by flow cytometry Homo sapiens 9.0 nM
Inhibition of JAK1/JAK3 in human PBMC assessed as decrease in IL2-induced STAT5 phosphorylation in CD3+ T cells preincubated for 1 hr followed by stimulation with IL2 for 15 mins by flow cytometry Homo sapiens 592.0 nM
Inhibition of JAK1 in human PBMC assessed as decrease in IL6-induced STAT5 phosphorylation in CD3+ T cells Homo sapiens 615.0 nM
Inhibition of JAK1/JAK2 in in human whole blood assessed as decrease in IL6-induced STAT3 phosphorylation in CD3+ T cells Homo sapiens 609.0 nM
Inhibition of BMPR2 (unknown origin) Homo sapiens 193.0 nM
Inhibition of human ERG at 10 uM by patch-clamp assay relative to control Homo sapiens 26.0 %
Antiinflammatory activity in CD40-induced colitis model of SCID mouse assessed as inhibition of IL-2 driven body weight loss at 50 mg/kg, po administered twice daily relative to control Mus musculus 99.0 %
Allosteric inhibition of fluorescein labeled probe binding to His-tagged recombinant human TYK2 pseudokinase JH2 domain (575-869 residues) incubated for 1 hr by HTRF assay Homo sapiens 0.2 nM
Inhibition of fluorescein labeled probe binding to His-tagged human TYK2 pseudokinase domain (575-869 residues) by Morrison titration based HTRF assay Homo sapiens 0.02 nM
Inhibition of fluorescein labeled probe binding to human recombinant JAK1 JH2 incubated for 1 hr by HTRF assay Homo sapiens 1.0 nM
Antiinflammatory activity in CD40-induced colitis model of SCID mouse assessed as inhibition of histological scores in intestine at 50 mg/kg, po administered twice daily relative to control Mus musculus 70.0 %
Binding affinity to TYK2 pseudokinase domain (unknown origin) Homo sapiens 0.02 nM
Inhibition of TYK2 in human whole blood assessed as reduction in IFN-alpha stimulated TYK2 phosphorylation Homo sapiens 13.0 nM
Inhibition of TYK2 JH2 domain (unknown origin) by HTRF assay Homo sapiens 0.2 nM
Inhibition of TYK2 in IFN-alpha stimulated human Kit225 T cells by luciferase reporter gene assay Homo sapiens 5.3 nM
Inhibition of TYK2 in human whole blood assessed as decrease in IFNalpha-induced STAT5 phosphorylation Homo sapiens 18.0 nM

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL4596392
FDA SRS N0A21N6RAU
PDB LB7
PubChem 134821691
ChEMBL CHEMBL4435170
FDA SRS N0A21N6RAU
Guide to Pharmacology 10432
PubChem 134821691
SureChEMBL SCHEMBL20520348
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