U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C16H17N7O2S
Molecular Weight 371.417
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BARICITINIB

SMILES

CCS(=O)(=O)N1CC(CC#N)(C1)N2C=C(C=N2)C3=C4C=CNC4=NC=N3

InChI

InChIKey=XUZMWHLSFXCVMG-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C16H17N7O2S
Molecular Weight 371.417
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Baricitinib (trade name Olumiant) is an investigational drug for rheumatoid arthritis (RA), being developed by Incyte and Eli Lilly. Baricitinib is a selective JAK1 and JAK2 inhibitor with IC50 of 5.9 nM and 5.7 nM in cell-free assays. In February 2017 Baricitinib was approved for use in the European Union as a second-line therapy for moderate to severe active rheumatoid arthritis in adults, either alone or in combination with methotrexate. On 31 May 2018 FDA approved Barictinib for the treatment of adult patients with moderately to severely active rheumatoid arthritis who have had an inadequate response to one or more TNF antagonist therapies.

CNS Activity

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
OLUMIANT
PubMed

PubMed

TitleDatePubMed
Selective inhibition of JAK1 and JAK2 is efficacious in rodent models of arthritis: preclinical characterization of INCB028050.
2010 May 1
Patents

Sample Use Guides

In Vivo Use Guide
Baricitinib 2 mg administered orally once daily.
Route of Administration: Oral
In Vitro Use Guide
Baricitinib inhibits IL-6–stimulated phosphorylation of the canonical substrate STAT3 (pSTAT3) and subsequent production of the chemokine MCP-1 with IC50 values of 44 nM and 40 nM, respectively, in PBMCs. Baricitinib also inhibits pSTAT3 stimulated by IL-23 with IC50 of 20 nM in isolated naive T-cells
Substance Class Chemical
Created
by admin
on Tue Mar 06 10:43:25 UTC 2018
Edited
by admin
on Tue Mar 06 10:43:25 UTC 2018
Record UNII
ISP4442I3Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BARICITINIB
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
BARICITINIB [INN]
Common Name English
BARICITINIB [WHO-DD]
Common Name English
LY3009104
Code English
BARICITINIB [USAN]
Common Name English
3-AZETIDINEACETONITRILE, 1-(ETHYLSULFONYL)-3-(4-(7H-PYRROLO(2,3-D)PYRIMIDIN-4-YL)-1H-PYRAZOL-1-YL)-
Systematic Name English
BARICITINIB [JAN]
Common Name English
INCB028050
Code English
INCB-028050
Code English
LY-3009104
Code English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS OLUMIANT (AUTHORIZED: ARTHRITIS, RHEUMATOID)
Created by admin on Tue Mar 06 10:43:25 UTC 2018 , Edited by admin on Tue Mar 06 10:43:25 UTC 2018
WHO-ATC L04AA37
Created by admin on Tue Mar 06 10:43:25 UTC 2018 , Edited by admin on Tue Mar 06 10:43:25 UTC 2018
Code System Code Type Description
PUBCHEM
44205240
Created by admin on Tue Mar 06 10:43:25 UTC 2018 , Edited by admin on Tue Mar 06 10:43:25 UTC 2018
PRIMARY
NCI_THESAURUS
C127012
Created by admin on Tue Mar 06 10:43:25 UTC 2018 , Edited by admin on Tue Mar 06 10:43:25 UTC 2018
PRIMARY
EVMPD
SUB180983
Created by admin on Tue Mar 06 10:43:25 UTC 2018 , Edited by admin on Tue Mar 06 10:43:25 UTC 2018
PRIMARY
ChEMBL
CHEMBL2105759
Created by admin on Tue Mar 06 10:43:25 UTC 2018 , Edited by admin on Tue Mar 06 10:43:25 UTC 2018
PRIMARY
CAS
1187594-09-7
Created by admin on Tue Mar 06 10:43:25 UTC 2018 , Edited by admin on Tue Mar 06 10:43:25 UTC 2018
PRIMARY
INN
9570
Created by admin on Tue Mar 06 10:43:25 UTC 2018 , Edited by admin on Tue Mar 06 10:43:25 UTC 2018
PRIMARY
EPA CompTox
1187594-09-7
Created by admin on Tue Mar 06 10:43:25 UTC 2018 , Edited by admin on Tue Mar 06 10:43:25 UTC 2018
PRIMARY
Related Record Type Details
EXCRETED UNCHANGED
URINE
METABOLIC ENZYME -> SUBSTRATE
Only 4 minor oxidative metabolites were identified (3 in urine; 1 in faeces) constituting approximately 5 % and 1 % of the dose, respectively.
TRANSPORTER -> SUBSTRATE
Coadministration of baricitinib with ciclosporin (Pgp/BCRP inhibitor) resulted in no clinically meaningful effects on baricitinib exposure.
TRANSPORTER -> SUBSTRATE
Coadministration of baricitinib with ciclosporin (Pgp/BCRP inhibitor) resulted in no clinically meaningful effects on baricitinib exposure.
TARGET -> INHIBITOR
EXCRETED UNCHANGED
FECAL
TRANSPORTER -> SUBSTRATE
A clinical pharmacology study, dosing of probenecid (an OAT3 inhibitor with strong inhibition potential) resulted in approximately a 2-fold increase in AUC(0-∞) with no change in tmax or Cmax of baricitinib.
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY