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Compound Detail

CHEMBL3622821

UPADACITINIB
💊 Approved Drug
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💊 Approved Drug
CC[C@@H]1CN(C(=O)NCC(F)(F)F)C[C@@H]1c1cnc2cnc3[nH]ccc3n12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3622821
Name UPADACITINIB
Phase Approved
Structure Type MOL
InChI Key WYQFJHHDOKWSHR-MNOVXSKESA-N
Therapeutic ✓ Yes

Known Names

ABT-494 Upadacitinib Upadacitinib anhydrous Upadacitinib component of abbv-599
32
Targets
157
Activities
4
Assay Types
4
PK Parameters
20
Publications
4
Known Names
13
Indications

Molecular Properties

380.4
MW (Da)
2.91
ALogP
4
HBA
2
HBD
78.3
PSA (Ų)
0.73
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2019
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -tinib
USAN Year 2015

Extended Properties

Molecular Formula C17H19F3N6O
MW 380.37
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.10

Indications

Alopecia Areata Arthritis, Juvenile Arthritis, Psoriatic Arthritis, Rheumatoid Colitis, Ulcerative Crohn Disease Dermatitis, Atopic Giant Cell Arteritis Hidradenitis Suppurativa Spondylitis, Ankylosing Takayasu Arteritis Vitiligo Lupus Erythematosus, Systemic

ATC Classification

L04AF03
upadacitinib
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Activity Summary

IC50 153 meas. best 9.1
Kd 2 meas. best 5.66
EC50 1 meas. best 7.85
Ki 1 meas. best 9.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase JAK1
CHEMBL2835
 IC50 9.1 7.6118 0.8 39
Tyrosine-protein kinase JAK1
CHEMBL2835
 Ki 9.05 9.05 0.9 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 8.8 6.847 1.6 27
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 8.8 7.2806 1.6 32
JAK3/JAK1
CHEMBL3038491
 IC50 8.7 8.028 2.0 5
JAK2/JAK1
CHEMBL3038492
 IC50 8.52 8.12 3.0 2
JAK1/TYK2
CHEMBL3301391
 IC50 8.4 7.86 4.0 2
Unchecked
CHEMBL612545
 EC50 7.85 7.85 14.0 1
Tyrosine-protein kinase JAK1
CHEMBL2968
 IC50 7.85 7.85 14.0 1
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 IC50 7.52 5.9129 30.0 14
Janus Kinase (JAK)
CHEMBL2363062
 IC50 7.35 7.35 45.0 1
Rho-associated protein kinase 2
CHEMBL2973
 IC50 6.38 6.38 420.0 2
Tyrosine-protein kinase JAK2
CHEMBL1649049
 IC50 6.23 6.23 593.0 1
Rho-associated protein kinase 1
CHEMBL3231
 IC50 6.04 6.04 920.0 2
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 5.82 5.82 1500.0 1
Tyrosine-protein kinase JAK3
CHEMBL5250
 IC50 5.73 5.73 1860.0 1
Cyclin-G-associated kinase
CHEMBL4355
 Kd 5.66 5.66 2200.0 1
Calcium/calmodulin-dependent protein kinase type 1D
CHEMBL5073
 IC50 5.64 5.64 2300.0 2
Proto-oncogene tyrosine-protein kinase receptor Ret
CHEMBL2041
 IC50 5.62 5.62 2400.0 2
Leukocyte tyrosine kinase receptor
CHEMBL5627
 IC50 5.57 5.57 2700.0 2
Non-receptor tyrosine-protein kinase TYK2
CHEMBL2321619
 IC50 5.57 5.57 2715.0 1
5'-AMP-activated protein kinase catalytic subunit alpha-1
CHEMBL4045
 IC50 5.35 5.35 4500.0 1
Aurora kinase A
CHEMBL4722
 IC50 5.35 5.35 4500.0 2
Fibroblast growth factor receptor 1
CHEMBL3650
 IC50 5.32 5.32 4800.0 2
Protein kinase C theta type
CHEMBL3920
 IC50 5.29 5.29 5100.0 2
Activated CDC42 kinase 1
CHEMBL4599
 IC50 5.29 5.29 5100.0 2
ALK tyrosine kinase receptor
CHEMBL4247
 IC50 5.26 5.26 5500.0 1
Aurora kinase B
CHEMBL2185
 IC50 5.26 5.26 5500.0 1
G protein-coupled receptor kinase 5
CHEMBL5678
 IC50 5.1 5.1 7900.0 1
Ribosomal protein S6 kinase alpha-3
CHEMBL2345
 IC50 5.02 5.02 9600.0 1
Serine/threonine-protein kinase 16
CHEMBL3938
 IC50 5.01 5.01 9700.0 2
AP2-associated protein kinase 1
CHEMBL3830
 Kd 5.0 5.0 9900.0 1
Tyrosine-protein kinase Lck
CHEMBL258
 IC50 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 83.0 ng.hr.mL-1 Rattus norvegicus
AUC 480.0 ng.hr.mL-1 Rattus norvegicus
AUC 83.0 ng.hr.mL-1 Rattus norvegicus
CL 25.0 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase JAK1 IC50 = 0.8 nM 9.1 Inhibition of JAK1 JH1 domain (unknown origin) using FITC-Ahx-KKSRGDYMTMQIG-NH2 ... 36657024
Tyrosine-protein kinase JAK1 Ki = 0.89 nM 9.05 Inhibition of recombinant human JAK1 (854 to 1154 residues) expressed in insect ... 30981576
Tyrosine-protein kinase JAK2 IC50 = 1.6 nM 8.8 Affinity Phenotypic Cellular interaction: (Cytokine potency assay (cytokine OSM,... -
Tyrosine-protein kinase JAK1 IC50 = 1.6 nM 8.8 Affinity Phenotypic Cellular interaction: (Cytokine potency assay (cytokine OSM,... -
Tyrosine-protein kinase JAK1 IC50 = 1.6 nM 8.8 Inhibition of JAK1 in human TF-1 cells assessed as reduction in OSM-induced STAT... 30886973
Tyrosine-protein kinase JAK3 IC50 = 1.6 nM 8.8 Affinity Phenotypic Cellular interaction: (Cytokine potency assay (cytokine OSM,... -
Tyrosine-protein kinase JAK1 IC50 = 2.0 nM 8.7 Affinity Phenotypic Cellular interaction: (Cytokine potency assay (cytokine IL-4... -
Tyrosine-protein kinase JAK2 IC50 = 2.0 nM 8.7 Affinity Phenotypic Cellular interaction: (Cytokine potency assay (cytokine IL-4... -
Tyrosine-protein kinase JAK3 IC50 = 2.0 nM 8.7 Affinity Phenotypic Cellular interaction: (Cytokine potency assay (cytokine IL-4... -
JAK3/JAK1 IC50 = 2.0 nM 8.7 Inhibition of JAK1/JAK3 in human HEKa cells assessed as reduction in IL-4-induce... 30886973
Tyrosine-protein kinase JAK1 IC50 = 3.0 nM 8.52 Affinity Phenotypic Cellular interaction: (Cytokine potency assay (cytokine IL-3... -
Tyrosine-protein kinase JAK2 IC50 = 3.0 nM 8.52 Affinity Phenotypic Cellular interaction: (Cytokine potency assay (cytokine IL-3... -
Tyrosine-protein kinase JAK3 IC50 = 3.0 nM 8.52 Affinity Phenotypic Cellular interaction: (Cytokine potency assay (cytokine IL-3... -
JAK2/JAK1 IC50 = 3.0 nM 8.52 Inhibition of JAK1/JAK2 in human HEKa cells assessed as reduction in IL-31-induc... 30886973
Tyrosine-protein kinase JAK2 IC50 = 3.1 nM 8.51 Inhibition of JAK2 JH1 domain (unknown origin) using Carboxyfluorescein-Ahx-GGEE... 36657024
Tyrosine-protein kinase JAK3 IC50 = 4.0 nM 8.4 Affinity Phenotypic Cellular interaction: (Cytokine potency assay (cytokine IL-1... -
Tyrosine-protein kinase JAK1 IC50 = 4.0 nM 8.4 Affinity Phenotypic Cellular interaction: (Cytokine potency assay (cytokine IL-1... -
JAK1/TYK2 IC50 = 4.0 nM 8.4 Inhibition of JAK1/TYK2 in human HEKa cells assessed as reduction in IL-13-induc... 30886973
Tyrosine-protein kinase JAK2 IC50 = 4.0 nM 8.4 Affinity Phenotypic Cellular interaction: (Cytokine potency assay (cytokine IL-1... -
Tyrosine-protein kinase JAK1 IC50 = 5.0 nM 8.3 Enzyme Inhibition Assay: Enzyme inhibition studies were performed using recombin... -

Literature References

PubMed DOI Target Context # Activities
30886973 10.1186/s41927-018-0031-x Rattus norvegicus 19
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5444388 Tyrosine-protein kinase JAK1 12
- 10.6019/CHEMBL5444388 Tyrosine-protein kinase JAK2 12
- 10.6019/CHEMBL5444388 Tyrosine-protein kinase JAK3 11
- 10.6019/CHEMBL4689842 U2OS 10
30886973 10.1186/s41927-018-0031-x Tyrosine-protein kinase JAK1 9
30886973 10.1186/s41927-018-0031-x Unchecked 8
38031930 10.1021/acs.jmedchem.3c01712 ADMET 8
- 10.6019/CHEMBL4689842 Fibroblast 8
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
- 10.6019/CHEMBL5465560 Tyrosine-protein kinase JAK3 5
30886973 10.1186/s41927-018-0031-x Tyrosine-protein kinase JAK3 5
30886973 10.1186/s41927-018-0031-x Tyrosine-protein kinase JAK2 5
31266686 10.1016/j.bmcl.2019.06.042 Unchecked 4
- 10.6019/CHEMBL5465560 Tyrosine-protein kinase JAK2 4
30981576 10.1016/j.bmcl.2019.04.008 Unchecked 4
38031930 10.1021/acs.jmedchem.3c01712 Mus musculus 4
29870256 10.1021/acs.jmedchem.8b00667 Tyrosine-protein kinase JAK2 4

Data from ChEMBL 36 via Core Engine