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Compound Detail

CHEMBL2105759

BARICITINIB
💊 Approved Drug
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💊 Approved Drug
CCS(=O)(=O)N1CC(CC#N)(n2cc(-c3ncnc4[nH]ccc34)cn2)C1

Basic Information

ChEMBL ID CHEMBL2105759
Name BARICITINIB
Phase Approved
Structure Type MOL
InChI Key XUZMWHLSFXCVMG-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Baricitinib Baricitinib phosphate Baricitinib phosphate salt INCB-028050 Incb-28050 INCB028050 LY-3009104 LY3009104 Olumiant
36
Targets
143
Activities
2
Assay Types
13
PK Parameters
20
Publications
9
Known Names
20
Indications
2
Mechanisms

Molecular Properties

371.4
MW (Da)
1.10
ALogP
7
HBA
1
HBD
120.6
PSA (Ų)
0.72
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2017
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -tinib
USAN Year 2011

Extended Properties

Molecular Formula C16H17N7O2S
MW 371.43
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -1.11

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Tyrosine-protein kinase JAK1 inhibitor INHIBITOR Tyrosine-protein kinase JAK1
Tyrosine-protein kinase JAK2 inhibitor INHIBITOR Tyrosine-protein kinase JAK2

Indications

Arthritis, Rheumatoid Alopecia Areata Arthritis, Juvenile Dermatitis, Atopic Dermatomyositis Dermatomyositis Influenza, Human Lupus Erythematosus, Systemic Pneumonia Sepsis Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Uveitis Brain Injuries Diabetes Mellitus, Type 1 Diabetic Nephropathies Giant Cell Arteritis HIV Infections Lichen Planus Liver Cirrhosis, Biliary

ATC Classification

L04AF02
baricitinib
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Drug Warnings

Black Box Warning
vascular toxicity
Country: United States
Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
respiratory toxicity
Country: United States
Black Box Warning
infectious disease
Country: United States

Activity Summary

IC50 102 meas. best 9.15
Kd 41 meas. best 8.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase JAK1
CHEMBL2835
IC50 9.15 8.3288 0.7 26
Tyrosine-protein kinase JAK2
CHEMBL2971
IC50 9.1 8.0133 0.8 30
JAK3/JAK1
CHEMBL3038491
IC50 8.3 7.154 5.0 5
AP2-associated protein kinase 1
CHEMBL3830
Kd 8.09 7.9963 8.2 8
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
IC50 8.06 7.4123 8.7 13
JAK1/TYK2
CHEMBL3301391
IC50 7.89 7.6975 13.0 4
JAK1/JAK2/TYK2
CHEMBL3301390
IC50 7.8 7.74 16.0 2
AP2-associated protein kinase 1
CHEMBL3830
IC50 7.77 7.77 17.0 1
Signal transducer and activator of transcription 3
CHEMBL4026
IC50 7.7 7.53 20.0 2
BMP-2-inducible protein kinase
CHEMBL4522
Kd 7.7 7.3567 20.0 3
Tyrosine-protein kinase JAK3
CHEMBL2148
IC50 7.6 6.5222 25.0 9
Unchecked
CHEMBL612545
IC50 7.4 6.998 40.0 5
Uncharacterized protein FLJ45252
CHEMBL4105933
Kd 7.11 7.11 78.0 1
JAK2/TYK2
CHEMBL3301392
IC50 7.09 6.8733 81.9 3
Septin-9
CHEMBL4105891
Kd 7.08 7.08 84.0 1
MAP/microtubule affinity-regulating kinase 3
CHEMBL5600
Kd 6.98 6.98 104.0 1
Serine/threonine-protein kinase N1
CHEMBL3384
Kd 6.98 6.98 104.0 1
Cyclin-G-associated kinase
CHEMBL4355
Kd 6.92 6.598 120.0 5
Unchecked
CHEMBL612545
Kd 6.9 6.19 126.0 2
Serine/threonine-protein kinase MARK2
CHEMBL3831
Kd 6.9 6.9 125.0 1
Cyclin-G-associated kinase
CHEMBL4355
IC50 6.87 6.87 136.0 1
Calcium/calmodulin-dependent protein kinase type II subunit gamma
CHEMBL3829
Kd 6.61 6.61 243.0 1
Casein kinase I isoform gamma-2
CHEMBL2543
Kd 6.58 6.58 265.0 1
Serine/threonine-protein kinase N2
CHEMBL3032
Kd 6.57 6.57 269.0 1
Calcium/calmodulin-dependent protein kinase type II subunit delta
CHEMBL2801
Kd 6.51 6.51 312.0 1
Eukaryotic translation initiation factor 2-alpha kinase 1
CHEMBL6029
Kd 6.47 6.47 335.0 1
Rho-associated protein kinase 1
CHEMBL3231
Kd 6.32 6.32 482.0 1
Non-receptor tyrosine-protein kinase TNK1
CHEMBL5334
Kd 6.21 6.21 622.0 1
Rho-associated protein kinase 2
CHEMBL2973
Kd 6.12 6.12 756.0 1
Dual specificity protein kinase CLK1
CHEMBL4224
Kd 6.11 6.11 778.0 1
Serine/threonine-protein kinase ULK1
CHEMBL6006
Kd 6.09 6.09 810.0 1
Proto-oncogene tyrosine-protein kinase receptor Ret
CHEMBL2041
Kd 6.01 6.01 973.0 1
Protein kinase C delta type
CHEMBL2996
Kd 5.97 5.97 1075.0 1
Casein kinase I isoform gamma-1
CHEMBL2426
Kd 5.76 5.76 1753.0 1
Mitogen-activated protein kinase kinase kinase 1
CHEMBL3956
Kd 5.72 5.72 1891.0 1
Protein kinase C alpha type
CHEMBL299
Kd 5.68 5.68 2071.0 1
cAMP-dependent protein kinase catalytic subunit alpha
CHEMBL4101
Kd 5.44 5.44 3597.0 1
Citron Rho-interacting kinase
CHEMBL5579
Kd 5.36 5.36 4361.0 1
Protein kinase C beta type
CHEMBL3045
Kd 4.58 4.58 26324.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1586.81 ng.hr.mL-1 Rattus norvegicus
AUC 3608.48 ng.hr.mL-1 Rattus norvegicus
CL 8.0 mL.min-1.g-1 Homo sapiens
CL 10.5 mL.min-1.kg-1 Rattus norvegicus
CL 23.17 mL.min-1.kg-1 Rattus norvegicus
CL 25.0 mL.min-1.g-1 Homo sapiens
Cmax 1774.76 nM Rattus norvegicus
F 45.48 % Rattus norvegicus
MRT 1.34 hr Rattus norvegicus
MRT 4.36 hr Rattus norvegicus
T1/2 1.96 hr Rattus norvegicus
T1/2 2.43 hr Rattus norvegicus
Tmax 1.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase JAK1 IC50 = 0.7 nM 9.15 Biochemical Activity Assay: The assays were performed in 384-well, low volume mi... -
Tyrosine-protein kinase JAK1 IC50 = 0.7 nM 9.15 Biochemical Activity Assay: The assays were performed in 384-well, low volume mi... -
Tyrosine-protein kinase JAK1 IC50 = 0.7 nM 9.15 Kinase Assay: A kinase selectivity panel which measures substrate peptide phosph... -
Tyrosine-protein kinase JAK2 IC50 = 0.8 nM 9.1 Inhibition of JAK2 (unknown origin) using Ulight-JAK1 substrate peptide assessed... 26701356
Tyrosine-protein kinase JAK1 IC50 = 0.99 nM 9.0 Inhibition of JAK1 (unknown origin) using Ulight-JAK1 substrate peptide assessed... 26701356
Tyrosine-protein kinase JAK1 IC50 = 2.4 nM 8.62 Inhibition of JAK1 JH1 domain (unknown origin) using FITC-Ahx-KKSRGDYMTMQIG-NH2 ... 36657024
Tyrosine-protein kinase JAK2 IC50 = 2.9 nM 8.54 Inhibition of JAK2 JH1 domain (unknown origin) using Carboxyfluorescein-Ahx-GGEE... 36657024
Tyrosine-protein kinase JAK2 IC50 = 4.0 nM 8.4 Kinase Assay: A kinase selectivity panel which measures substrate peptide phosph... -
Tyrosine-protein kinase JAK2 IC50 = 4.0 nM 8.4 Biochemical Activity Assay: The assays were performed in 384-well, low volume mi... -
Tyrosine-protein kinase JAK2 IC50 = 4.0 nM 8.4 Biochemical Activity Assay: The assays were performed in 384-well, low volume mi... -
Tyrosine-protein kinase JAK1 IC50 = 4.0 nM 8.4 Inhibition of JAK1 (unknown origin) 36439976
Tyrosine-protein kinase JAK1 IC50 = 4.0 nM 8.4 Inhibition of recombinant human N-terminal GST-tagged JAK1 (850 to 1154 residues... 33813153
Tyrosine-protein kinase JAK1 IC50 = 4.0 nM 8.4 Inhibition of recombinant human JAK1 using 5'FAM-KKSRGDYMTMQID as substrate in p... 29298069
Tyrosine-protein kinase JAK1 IC50 = 4.0 nM 8.4 Inhibition of JAK1 (unknown origin) 27137359
Tyrosine-protein kinase JAK1 IC50 = 4.0 nM 8.4 Inhibition of JAK1 (unknown origin) 24417533
JAK3/JAK1 IC50 = 5.0 nM 8.3 Inhibition of JAK1/JAK3 in human M07E cells assessed as reduction of IL-15 stimu... 36657024
Tyrosine-protein kinase JAK2 IC50 = 5.5 nM 8.26 Inhibition of JAK: The study of the effect of compounds on the activity of purif... -
Tyrosine-protein kinase JAK2 IC50 = 5.7 nM 8.24 Inhibition of recombinant epitope tagged JAK2 (unknown origin) (828 to 1132 resi... 35749986
Tyrosine-protein kinase JAK2 IC50 = 5.7 nM 8.24 Inhibition of JAK2 (unknown origin) 37057760
Tyrosine-protein kinase JAK2 IC50 = 5.7 nM 8.24 Inhibition of recombinant epitope tagged JAK2 (unknown origin) (828 to 1132 resi... 37163463

Literature References

PubMed DOI Target Context # Activities
33813153 10.1016/j.ejmech.2021.113394 ADMET 15
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
29191878 10.1126/science.aan4368 Unchecked 6
33691794 10.1186/s13148-021-01037-1 A549 4
31378597 10.1016/j.bmc.2019.07.037 RAW264.7 4
33813153 10.1016/j.ejmech.2021.113394 Tyrosine-protein kinase JAK2 3
32120325 10.1016/j.ejmech.2020.112155 Unchecked 3
37163463 10.1021/acs.jmedchem.3c00050 Unchecked 3
26351728 10.1021/acs.jmedchem.5b01263 Unchecked 3
38359535 10.1016/j.ejmech.2024.116210 Unchecked 3
35300081 10.1021/acsmedchemlett.1c00650 Unchecked 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
33539089 10.1021/acs.jmedchem.0c01467 AP2-associated protein kinase 1 3
26372653 10.1016/j.bmcl.2015.09.020 Tyrosine-protein kinase JAK2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
24417533 10.1021/jm401490p JAK2/TYK2 2
33570945 10.1021/acs.jmedchem.0c01952 Tyrosine-protein kinase JAK2 2
30926315 10.1016/j.bmc.2019.03.048 Tyrosine-protein kinase JAK1 2
30926315 10.1016/j.bmc.2019.03.048 Non-receptor tyrosine-protein kinase TYK2 2

Data from ChEMBL 36 via Core Engine