2HB

N-(5-{4-[(1,1-dioxidothiomorpholin-4-yl)methyl]phenyl}[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide


Toggle HydrogenToggle Labels

Chemical Component Summary

NameN-(5-{4-[(1,1-dioxidothiomorpholin-4-yl)methyl]phenyl}[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide
SynonymsG146034
IdentifiersN-[5-[4-[[1,1-bis(oxidanylidene)-1,4-thiazinan-4-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide
FormulaC21 H23 N5 O3 S
Molecular Weight425.504
TypeNON-POLYMER
Isomeric SMILESc1cc(n2c(c1)nc(n2)NC(=O)C3CC3)c4ccc(cc4)CN5CCS(=O)(=O)CC5
InChIInChI=1S/C21H23N5O3S/c27-20(17-8-9-17)23-21-22-19-3-1-2-18(26(19)24-21)16-6-4-15(5-7-16)14-25-10-12-30(28,29)13-11-25/h1-7,17H,8-14H2,(H,23,24,27)
InChIKeyRIJLVEAXPNLDTC-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count53
Chiral Atom Count0
Bond Count57
Aromatic Bond Count16

Drug Info: DrugBank

DrugBank IDDB14845 
NameFilgotinib
Groups
  • investigational
  • approved
DescriptionRheumatoid arthritis (RA) is a chronic, autoimmune, systemic, and inflammatory disease that causes synovial joint symptoms and can limit range of motion in severe cases.[A221451,A221456] The disease is associated with extra-articular manifestations, progressive disability, and comorbidities including cardiovascular disease and mental disorders.[A189165] 50-70% of patients with RA are unable to achieve sustained clinical remission despite the availability of several treatments including disease-modifying anti-rheumatic drugs (DMARDS) like [methotrexate], interleukin-6 (IL-6) blockers, and tumor necrosis factor (TNF) inhibitors.[A189165] New therapeutic developments target other inflammatory pathways implicated in RA including the Janus kinase (JAK) signaling pathway as seen with filgotinib.[A221456] There are four JAK subtypes which include JAK1, JAK2, JAK3, and tyrosine kinase 2.[A189165] Non-selective JAK inhibitors like [tofacitinib] target JAK1 and JAK3 subtypes with minimal activity at JAK2. In contrast, the newly approved filgotinib is a highly selective JAK1 inhibitor.[A189165] JAK2 and JAK3 play important roles in both immune and hematologic functions; therefore, selectivity for JAK1 aims to improve the safety profile of filgotinib while maintaining clinical efficacy.[A189165] Filgotinib is currently reserved for patients who cannot tolerate DMARDs, or who have been unable to achieve remission in response to one or more DMARDs.[L16616]
Synonyms
  • Filgotinib
  • Filgotinib maleate
Brand NamesJyseleca
IndicationFilgotinib is indicated for the treatment of active moderate to severe rheumatoid arthritis alone or in combination with methotrexate.[L16616] Filgotinib is currently reserved for patients who are unable to tolerate or who have not responded adequately to one or more disease-modifying anti-rheumatic drugs (DMARDS).[L16616] Filgotinib is also indicated for treatment of moderately to severely active ulcerative colitis in adult patients who had an inadequate response with, lost response to, or were intolerant to either conventional therapy or a biologic agent.[L39209]
Categories
  • Antineoplastic and Immunomodulating Agents
  • Arthritis, Rheumatoid, drug therapy
  • Immunosuppressive Agents
  • Janus Kinase 1, antagonists & inhibitors
  • Janus Kinases, antagonists & inhibitors
ATC-CodeL04AA45
CAS number1206161-97-8

Drug Targets

NameTarget SequencePharmacological ActionActions
Tyrosine-protein kinase JAK1MQYLNIKEDCNAMAFCAKMRSSKKTEVNLEAPEPGVEVIFYLSDREPLRL...unknowninhibitor
Cocaine esteraseMRLHRLRARLSAVACGLLLLLVRGQGQDSASPIRTTHTGQVLGSLVHVKG...unknownmetabolizer
Liver carboxylesterase 1MWLRAFILATLSASAAWGHPSSPPVVDTVHGKVLGKFVSLEGFAQPVAIF...unknownmetabolizer
P-glycoprotein 1MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...unknownsubstrate
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

Related Resource References

Resource NameReference
Pharos CHEMBL3301607
PubChem 49831257
ChEMBL CHEMBL3301607
CCDC/CSD LIKFIX, LIKFAP, LIKFET