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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2 entries where 2HB is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	53
Chiral Atom Count	0
Bond Count	57
Aromatic Bond Count	16

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Chemical Component Summary
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
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
Name	Filgotinib
Groups	investigational approved
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	Filgotinib maleate Filgotinib
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	Antineoplastic and Immunomodulating Agents Arthritis, Rheumatoid, drug therapy Immunosuppressive Agents Janus Kinase 1, antagonists & inhibitors Janus Kinase Inhibitor Janus Kinases, antagonists & inhibitors P-glycoprotein substrates Selective Immunosuppressants
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