3JW

Baricitinib

Created:	2014-08-28
Last modified:	2014-09-05

Find Related PDB Entry
3 entries where 3JW is found as a standalone ligand

Help Find related ligands:
Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Help

Find related ligands:

Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Chemical Details
Formal Charge	0
Atom Count	43
Chiral Atom Count	0
Bond Count	46
Aromatic Bond Count	15

Toggle Hydrogen Toggle Labels

Chemical Component Summary
Name	Baricitinib
Systematic Name (OpenEye OEToolkits)	2-[1-ethylsulfonyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]ethanenitrile
Formula	C₁₆ H₁₇ N₇ O₂ S
Molecular Weight	371.417
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=S(=O)(N4CC(n3ncc(c2ncnc1c2ccn1)c3)(C4)CC#N)CC
SMILES	CACTVS	3.385	CC[S](=O)(=O)N1CC(CC#N)(C1)n2cc(cn2)c3ncnc4[nH]ccc34
SMILES	OpenEye OEToolkits	1.9.2	CCS(=O)(=O)N1CC(C1)(CC#N)n2cc(cn2)c3c4cc[nH]c4ncn3
Canonical SMILES	CACTVS	3.385	CC[S](=O)(=O)N1CC(CC#N)(C1)n2cc(cn2)c3ncnc4[nH]ccc34
Canonical SMILES	OpenEye OEToolkits	1.9.2	CCS(=O)(=O)N1CC(C1)(CC#N)n2cc(cn2)c3c4cc[nH]c4ncn3
InChI	InChI	1.03	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	InChI	1.03	XUZMWHLSFXCVMG-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB11817
Name	Baricitinib
Groups	approved investigational
Description	Baricitinib is a Janus kinase (JAK) inhibitor. JAKs are tyrosine protein kinases that play an important role in pro-inflammatory signaling pathways. Overactive JAKs have been implicated in autoimmune disorders, such as rheumatoid arthritis. By inhibiting the actions of JAK1 and JAK2, baricitinib attenuates JAK-mediated inflammation and immune responses.[L41760] Baricitinib was first approved by the European Commission (EC) in February 2017 for the treatment of rheumatoid arthritis in adults [A248395] and was later approved by the FDA in 2018.[A248400] The EC later approved baricitinib for the treatment of atopic dermatitis, making it the first JAK inhibitor used for this indication in Europe.[A248405] While baricitinib was granted emergency use as a treatment for COVID-19 in combination with [remdesivir] under the Emergency Use Authorization (EUA) in November 2020,[L22619] the FDA fully approved the use of baricitinib for the treatment of COVID-19 in May 2022.[L41760]
Synonyms	Baricitinib
Brand Names	Baricitinib Olumiant
Indication	In the US and Europe, baricitinib is indicated for the treatment of adult patients with moderately to severely active rheumatoid arthritis who have had an inadequate response to one or more TNF blockers. Baricitinib may be used as monotherapy or in combination with [methotrexate] [L41760,L41770] or other DMARDs.[L41760] In Europe, baricitinib is indicated for the treatment of moderate to severe atopic dermatitis in adult patients who are candidates for systemic therapy.[L41770] In the US, baricitinib is also indicated for the treatment of coronavirus disease 2019 (COVID-19) in hospitalized adults requiring supplemental oxygen, non-invasive or invasive mechanical ventilation, or extracorporeal membrane oxygenation.[L41760] Recently, it is also approved as the treatment for severe alopecia areata in adults.[L42070]
Categories	Amides Antineoplastic and Immunomodulating Agents Antirheumatic Agents Azetines BCRP/ABCG2 Inhibitors BCRP/ABCG2 Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Substrates Disease-modifying Antirheumatic Agents Drugs that are Mainly Renally Excreted Experimental Unapproved Treatments for COVID-19 Heterocyclic Compounds, Fused-Ring Immunosuppressive Agents Janus Kinase Inhibitor Janus Kinase Inhibitors MATE 2 Inhibitors MATE 2 Substrates MATE 2 Substrates with a Narrow Therapeutic Index MATE inhibitors MATE substrates Narrow Therapeutic Index Drugs OAT1/SLC22A6 inhibitors OAT3/SLC22A8 Inhibitors OAT3/SLC22A8 Substrates OAT3/SLC22A8 Substrates with a Narrow Therapeutic Index OATP1B3 inhibitors OCT2 Inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Selective Immunosuppressants Sulfones Sulfur Compounds
ATC-Code	L04AA37
CAS number	1187594-09-7

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Tyrosine-protein kinase JAK1	MQYLNIKEDCNAMAFCAKMRSSKKTEVNLEAPEPGVEVIFYLSDREPLRL...	unknown	inhibitor
Tyrosine-protein kinase JAK2	MGMACLTMTEMEGTSTSSIYQNGDISGNANSMKQIDPVLQVYLYHSLGKS...	unknown	inhibitor
Tyrosine-protein kinase JAK3	MAPPSEETPLIPQRSCSLLSTEAGALHVLLPARGPGPPQRLSFSFGDHLA...	unknown	inhibitor
Non-receptor tyrosine-protein kinase TYK2	MPLRHWGMARGSKPVGDGAQPMAAMGGLKVLLHWAGPGGGEPWVTFSESS...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Solute carrier family 22 member 8	MTFSEILDRVGSMGHFQFLHVAILGLPILNMANHNLLQIFTAATPVHHCR...	unknown	substrate,inhibitor
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate,inhibitor
Multidrug and toxin extrusion protein 2	MDSLQDTVALDHGGCCPALSRLVPRGFGTEMWTLFALSGPLFLFQVLTFM...	unknown	substrate,inhibitor
Solute carrier family 22 member 6	MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...	unknown	inhibitor
Solute carrier family 22 member 2	MPTTVDDVLEHGGEFHFFQKQMFFLLALLSATFAPIYVGIVFLGFTPDHR...	unknown	inhibitor
Solute carrier organic anion transporter family member 1B3	MDQHQHLNKTAESASSEKKKTRRCNGFKMFLAALSFSYIAKALGGIIMKI...	unknown	inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate
View More

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682