SML1960
GSK583
≥98% (HPLC)
Synonym(s):
GSK583, 6-(tert-Butylsulfonyl)-N-(5-fluoro-1H-indazol-3-yl)quinolin-4-amine, GSK′583, GSK-2616583A
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About This Item
Empirical Formula (Hill Notation):
C20H19FN4O2S
CAS Number:
Molecular Weight:
398.45
UNSPSC Code:
51111800
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Storage condition:
desiccated, protect from light
Quality Segment
assay
≥98% (HPLC)
form
powder
storage condition
desiccated, protect from light
color
white to beige
solubility
DMSO: 20 mg/mL, clear
storage temp.
2-8°C
SMILES string
Fc1cc2c([nH]nc2Nc3c4c(ncc3)ccc(c4)[S](=O)(=O)C(C)(C)C)cc1
InChI key
XLOGLWKOHPIJLV-UHFFFAOYSA-N
Biochem/physiol Actions
An ATP-competitive RIP2 (RIPK2) inhibitor with in vitro and in vivo efficacy against NOD1- and NOD2-dependent pro-inflammatory cytokines release.
GSK583 is a cell-permeable indazolylquinolinamine that acts as an ATP-competitive (IC50 = 2 & 5 nM using rat & human RIPK2, respectively) inhibitor against RIPK2 kinase activity (66.6% inhibition at 1 μM; [ATP] = 10 μM), exhibiting much reduced or no inhibitory potency against a panel of 209 other kinases <34% inhibition at 1 μM; [ATP] = 10 ?M). GSK583 selectively inhibits against NOD1- and NOD2-, but not TLR2-, TLR4-, TLR7-. IL-1R-, or TNFR-dependent pro-inflammatory cytokines release (>95% inhibition vs. <40% inhibition at 1 ?M using primary human monocytes stimulated with respective ligands). GSK583 effectively inhibits TNF? and IL-6 production from Crohn′s disease (CD) and ulcerative colitis (UC) patients intestinal explant cultures ex vivo (IC50 = 200 nM) and is efficacious against NOD1 ligand FK156- and NOD2 ligand MDP-induced inflammatory responses in mice and rats (10 mg/kg p.o.) in vivo.
Storage Class
11 - Combustible Solids
WGK
WGK 3
Flash Point (°F)
Not applicable
Flash Point (°C)
Not applicable
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