UPADACITINIB

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC L04AA44
UNII 4RA0KN46E0

Structure

InChI Key WYQFJHHDOKWSHR-MNOVXSKESA-N
Smiles CC[C@@H]1CN(C(=O)NCC(F)(F)F)C[C@@H]1c1cnc2cnc3[nH]ccc3n12
InChI
InChI=1S/C17H19F3N6O/c1-2-10-7-25(16(27)24-9-17(18,19)20)8-11(10)13-5-22-14-6-23-15-12(26(13)14)3-4-21-15/h3-6,10-11,21H,2,7-9H2,1H3,(H,24,27)/t10-,11+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H19F3N6O
Molecular Weight 380.37
AlogP 2.91
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 3.0
Polar Surface Area 78.32
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 27.0

Bioactivity

Mechanism of Action Action Reference
Janus Kinase (JAK) inhibitor INHIBITOR FDA
Protein: Janus Kinase (JAK)
Description: Tyrosine-protein kinase JAK2
Organism : Homo sapiens
O60674 ENSG00000096968
Protein: Janus Kinase (JAK)
Description: Tyrosine-protein kinase JAK1
Organism : Homo sapiens
P23458 ENSG00000162434
Protein: Janus Kinase (JAK)
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
- 8-608 - 1 -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakB family
- 8-608 - 1 -
Assay Description Organism Bioactivity Reference
Inhibition of JAK1 (unknown origin) by cell-based assay Homo sapiens 8.0 nM
Inhibition of JAK2 (unknown origin) by cell-based assay Homo sapiens 600.0 nM
Inhibition of recombinant JAK2 (unknown origin) in presence of 0.1 mM ATP by alpha-screen assay Homo sapiens 8.0 nM
Inhibition of JAK2 in human TF1 cells assessed as reduction in IL2-induced STAT6 phosphorylation at Tyr694/699 residues Homo sapiens 608.0 nM
Inhibition of recombinant JAK1 (unknown origin) by alpha-screen assay Homo sapiens 43.0 nM
Inhibition of recombinant JAK2 (unknown origin) by alpha-screen assay Homo sapiens 120.0 nM
Inhibition of JAK1 (unknown origin) by cell based assay Homo sapiens 8.0 nM
Inhibition of JAK2 (unknown origin) by cell based assay Homo sapiens 600.0 nM
Inhibition of recombinant C-terminal His6-tagged human JAK2 kinase domain (808 to end residues) expressed in baculovirus-infected Sf21 cells in presence of 0.1 mM ATP Homo sapiens 120.0 nM
Inhibition of GST-fused recombinant human JAK1 catalytic domain (845-1142 residues) expressed in Sf9 cells in presence of 0.1 mM ATP Homo sapiens 47.0 nM
Inhibition of recombinant human BCR-JAK1 expressed in mouse Ba/F3 cells assessed as reduction in pSTAT5 level incubated for 30 mins by AlphaScreen assay Homo sapiens 14.0 nM
Inhibition of recombinant human JAK1 (854 to 1154 residues) expressed in insect cells using Y1-B as substrate incubated for 30 mins by microfluidic mobility shift assay Homo sapiens 0.89 nM
Inhibition of JAK in human BEAS-2B cells assessed as reduction in IL13-induced STAT6 phosphorylation incubated for 1 hr followed by IL13 addition and measured after 15 mins by immunofluorescence assay Homo sapiens 45.0 nM

Cross References

Resources Reference
ChEMBL CHEMBL3622821
DrugBank DB15091
DrugCentral 5346
FDA SRS 4RA0KN46E0
Guide to Pharmacology 9246
PubChem 58557659
SureChEMBL SCHEMBL9991056
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