Ketcher 11302114052D 1   1.00000     0.00000     0

 26 29  0     0  0            999 V2000
   16.8678  -13.7876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5543  -14.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3680  -15.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1750  -14.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8681  -13.7876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3680  -16.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2284  -16.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1823  -16.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7691  -17.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1823  -18.1293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2284  -17.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3680  -18.3230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5008  -17.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5008  -16.8222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8998  -12.6003    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.8870  -12.7538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6940  -12.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2739  -12.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4739  -13.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0878  -12.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9812  -11.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8745  -10.3991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2724  -13.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2839  -13.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1205  -11.9729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0535  -11.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0     0  0
  2  3  2  0     0  0
  3  4  1  0     0  0
  4  5  2  0     0  0
  5  1  1  0     0  0
  3  6  1  0     0  0
  6  7  2  0     0  0
  7  8  1  0     0  0
  8  9  2  0     0  0
  9 10  1  0     0  0
 10 11  1  0     0  0
 11  7  1  0     0  0
 11 12  2  0     0  0
 12 13  1  0     0  0
 13 14  2  0     0  0
 14  6  1  0     0  0
 15 16  1  0     0  0
 16 17  1  0     0  0
 17 18  1  0     0  0
 18 19  1  0     0  0
 19 16  1  0     0  0
 18 20  1  0     0  0
 20 21  1  0     0  0
 21 22  3  0     0  0
 18  1  1  0     0  0
 15 23  1  0     0  0
 23 24  1  0     0  0
 15 25  2  0     0  0
 15 26  2  0     0  0
M  END
> <ID>
CHEBI:95341

> <NAME>
baricitinib

> <DEFINITION>
A pyrrolopyrimidine that is 7H-pyrrolo[2,3-d]pyrimidine substituted by a 1-[3-(cyanomethyl)-1-(ethanesulfonyl)azetidin-3-yl]-1H-pyrazol-4-yl group at position 5. It is an FDA approved selective Janus Kinase 1 and 2 (JAK1 and JAK2) inhibitor used for the treatment of rheumatoid arthritis.

> <STAR>
3

> <SYNONYM>
LY3009104; LY-3009104; LY 3009104; INCB028050; INCB-028050; INCB 028050; 2-(3-(4-(3H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-1-(ethylsulfonyl)azetidin-3-yl)acetonitrile; 1-(ethylsulfonyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-3-azetidineacetonitrile

> <IUPAC_NAME>
{1-(ethylsulfonyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile

> <INN>
baricitinibum; baricitinib; baricitinib; baricitinib

> <BRAND_NAME>
Olumiant

> <FORMULA>
C16H17N7O2S

> <MASS>
371.420

> <MONOISOTOPIC_MASS>
371.11644

> <CHARGE>
0

> <SMILES>
CCS(=O)(=O)N1CC(CC#N)(C1)N1C=C(C=N1)C1=C2C=CNC2=NC=N1

> <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)

> <INCHIKEY>
XUZMWHLSFXCVMG-UHFFFAOYSA-N

> <CAS_REGISTRY_NUMBER>
1187594-09-7

> <CHEMIDPLUS>
1187594-09-7

> <DRUGBANK_ACCESSION>
DB11817

> <KEGG_DRUG_ACCESSION>
D10308

> <LINCS_ACCESSION>
LSM-6709

> <PDBECHEM_ACCESSION>
3JW

> <WIKIPEDIA_ACCESSION>
Baricitinib

> <PUBMED_CENTRAL_CITATION>
PMC8606629

> <PUBMED_CITATION>
26853940; 27910962; 30036348; 30871014; 30907116; 32856090; 33451175; 33456084; 33502499; 33870531; 33961266; 34110416; 34195587; 34237007; 34247230; 34250455; 34321249; 34358107; 34379541; 34393789; 34424311; 34468689; 34501467; 34553429; 34647989; 34747511; 34785883

$$$$