baricitinib   Click here for help

GtoPdb Ligand ID: 7792

Synonyms: INCB-028050 | INCB028050 | LY-3009104 | LY3009104 | Olumiant®
Approved drug PDB Ligand Immunopharmacology Ligand
baricitinib is an approved drug (EMA (2017), FDA (2018))
Compound class: Synthetic organic
Comment: Baricitinib is a JAK1 and 2 selective inhibitor. The compound is orally bioavailable.

SARS-CoV-2 and COVID-19: Through the application of proprietary artificial intelligence (AI) algorithms baricitinib has been predicted to possess antiviral activity in addition to its known anti-inflammatory efficacy [1,8-9]. Antiviral activity is predicted to arise from inhibition of the numb-associated kinase (NAK) AAK1 which is an important regulator of clathrin-mediated endocytosis. Inhibition of AAK1 would likely reduce the ability of viruses to infect lung cells, and is being proposed as a pharmacological mechanism that warrants further investigation as a treatment for SARS-CoV-2 infection (COVID-19 disease). In addition, the powerful anti-inflammatory activity of baricitinib (and potentially other approved JAK inhibitors such as fedratinib, and ruxolitinib) is likely to be effective against the pathological effects of raised cytokine levels (e.g. interferon γ) in patients with severe COVID-19. Short term use of baricitinib during the course of SARS-CoV-2 infection (7-14 days) is not anticipated to cause serious side-effects.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 128.94
Molecular weight 371.12
XLogP 0.41
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES N#CCC1(CN(C1)S(=O)(=O)CC)n1ncc(c1)c1ncnc2c1cc[nH]2
Isomeric SMILES N#CCC1(CN(C1)S(=O)(=O)CC)n1ncc(c1)c1ncnc2c1cc[nH]2
InChI InChI=1S/C16H17N7O2S/c1-2-26(24,25)22-9-16(10-22,4-5-17)23-8-12(7-21-23)14-13-3-6-18-15(13)20-11-19-14/h3,6-8,11H,2,4,9-10H2,1H3,(H,18,19,20)
InChI Key XUZMWHLSFXCVMG-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA (2017), FDA (2018))
IUPAC Name Click here for help
2-(3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-1-(ethylsulfonyl)azetidin-3-yl)acetonitrile
International Nonproprietary Names Click here for help
INN number INN
9570 baricitinib
Synonyms Click here for help
INCB-028050 | INCB028050 | LY-3009104 | LY3009104 | Olumiant®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9678829
Reactome Reaction Reactome logo R-HSA-9678737, R-HSA-9678935, R-HSA-9678561, R-HSA-9679028
Other databases
CAS Registry No. 1187594-09-7
ChEMBL Ligand CHEMBL2105759
DrugCentral Ligand 5202
GtoPdb PubChem SID 223366123
PubChem CID 44205240
RCSB PDB Ligand 3JW
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Wikipedia Baricitinib