2HB
N-(5-{4-[(1,1-dioxidothiomorpholin-4-yl)methyl]phenyl}[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide
| Created: | 2014-03-28 |
| Last modified: | 2020-06-05 |
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Chemical Details | |
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| Formal Charge | 0 |
| Atom Count | 53 |
| Chiral Atom Count | 0 |
| Bond Count | 57 |
| Aromatic Bond Count | 16 |
Chemical Component Summary | |
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| Name | N-(5-{4-[(1,1-dioxidothiomorpholin-4-yl)methyl]phenyl}[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide |
| Synonyms | G146034 |
| Systematic Name (OpenEye OEToolkits) | N-[5-[4-[[1,1-bis(oxidanylidene)-1,4-thiazinan-4-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide |
| Formula | C21 H23 N5 O3 S |
| Molecular Weight | 425.504 |
| Type | NON-POLYMER |
Chemical Descriptors | |||
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| Type | Program | Version | Descriptor |
| SMILES | ACDLabs | 12.01 | O=S5(=O)CCN(Cc4ccc(c2cccc1nc(nn12)NC(=O)C3CC3)cc4)CC5 |
| SMILES | CACTVS | 3.385 | O=C(Nc1nn2c(cccc2c3ccc(CN4CC[S](=O)(=O)CC4)cc3)n1)C5CC5 |
| SMILES | OpenEye OEToolkits | 1.9.2 | c1cc(n2c(c1)nc(n2)NC(=O)C3CC3)c4ccc(cc4)CN5CCS(=O)(=O)CC5 |
| Canonical SMILES | CACTVS | 3.385 | O=C(Nc1nn2c(cccc2c3ccc(CN4CC[S](=O)(=O)CC4)cc3)n1)C5CC5 |
| Canonical SMILES | OpenEye OEToolkits | 1.9.2 | c1cc(n2c(c1)nc(n2)NC(=O)C3CC3)c4ccc(cc4)CN5CCS(=O)(=O)CC5 |
| InChI | InChI | 1.03 | InChI=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) |
| InChIKey | InChI | 1.03 | RIJLVEAXPNLDTC-UHFFFAOYSA-N |
Drug Info: DrugBank
| DrugBank ID | DB14845? |
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| Name | Filgotinib |
| Groups |
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| Description | Rheumatoid 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 |
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| Brand Names | Jyseleca |
| Indication | Filgotinib 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 |
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| ATC-Code | L04AF04 |
| CAS number | 1206161-97-8 |
Drug Targets
| Name | Target Sequence | Pharmacological Action | Actions |
|---|---|---|---|
| Tyrosine-protein kinase JAK1 | MQYLNIKEDCNAMAFCAKMRSSKKTEVNLEAPEPGVEVIFYLSDREPLRL... | unknown | inhibitor |
| Cocaine esterase | MRLHRLRARLSAVACGLLLLLVRGQGQDSASPIRTTHTGQVLGSLVHVKG... | unknown | metabolizer |
| Liver carboxylesterase 1 | MWLRAFILATLSASAAWGHPSSPPVVDTVHGKVLGKFVSLEGFAQPVAIF... | unknown | metabolizer |
| ATP-dependent translocase ABCB1 | MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY... | unknown | substrate |
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 Name | Reference |
|---|---|
| Pharos | CHEMBL3301607 |
| PubChem | 49831257 |
| ChEMBL | CHEMBL3301607 |
| CCDC/CSD | LIKFIX, LIKFAP, LIKFET |
