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SML2102

Sigma-Aldrich

GSK256066

Synonym(s):

6-({3-[(Dimethylamino)carbonyl]phenyl}sulfonyl)-8-methyl-4-{[3-(methoxy)phenyl]amino}-3-quinolinecarboxamide, 6-[[3-[(Dimethylamino)carbonyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methyl-3-quinolinecarboxamide, GSK 256066, GSK-256066

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About This Item

Empirical Formula (Hill Notation):
C27H26N4O5S
CAS Number:
801312-28-7
Molecular Weight:
518.58
MDL number:
MFCD18206923
UNSPSC Code:
51111800

assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

InChI

1S/C27H26N4O5S/c1-16-11-21(37(34,35)20-10-5-7-17(12-20)27(33)31(2)3)14-22-24(16)29-15-23(26(28)32)25(22)30-18-8-6-9-19(13-18)36-4/h5-15H,1-4H3,(H2,28,32)(H,29,30)

InChI key

JFHROPTYMMSOLG-UHFFFAOYSA-N

Biochem/physiol Actions

GSK256066 is a reversible and cAMP-competitive phosphodiesterase 4 (PDE4) inhibitor that targets all PDE4 subtypes with high affinity (IC50 = 53.7 pM against 2 nM [3H]-rolipram for binding HRBS in rat brain cytosol), potency and selectivity (pIC50 ≥11.31/11.5/11.42/11.94 against PDE4A/B/C/D vs. pIC50 = 5.73/5.92/5.93/5.39/5.28/8.11 against PDE1/2/3/5/6/7 by SPA assays). GSK256066 effectively inhibits LPS-induced TNFα production from human whole blood and isolated PBMCs (pIC50 = 126 and 10 pM, respectively) in vitro and acute pulmonary neutrophilia in rats in vivo (ED50 = 1.1 μg/kg, administered intratracheally 2 hrs priror to LPS). GSK256066 is shown to be more potent than Cilomilast (SB-207499) and Roflumilast in both cell-free and cell-based assays.

wgk_germany

WGK 3

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Anthony T Nials et al.
The Journal of pharmacology and experimental therapeutics, 337(1), 137-144 (2011-01-06)
Oral phosphodiesterase (PDE) 4 inhibitors have demonstrated clinical efficacy in chronic obstructive pulmonary disease and asthma. Preclinical and clinical investigation of inhaled PDE4 inhibitors is ongoing. 6-({3-[(Dimethylamino)carbonyl]phenyl}sulfonyl)-8-methyl-4-{[3-methyloxy)phenyl]amino}-3-quinolinecarboxamide (GSK256066) is an exceptionally high-affinity and selective inhibitor of PDE4 designed for inhaled
Seamus Grundy et al.
Respiratory research, 17, 9-9 (2016-01-27)
CD8 lymphocytes play an important role in the pathogenesis of COPD. Corticosteroids and phosphodiesterase 4 (PDE4) inhibitors are anti-inflammatory drugs used for COPD treatment. Little is known of the combined effect of these drugs on COPD CD8 cells. We studied
Dave Singh et al.
Respiratory research, 11, 26-26 (2010-03-03)
GSK256066 is a selective phosphodiesterase 4 inhibitor that can be given by inhalation, minimising the potential for side effects. We evaluated the effects of GSK256066 on airway responses to allergen challenge in mild asthmatics. In a randomised, double blind, cross-over
Michael D Woodrow et al.
Bioorganic & medicinal chemistry letters, 19(17), 5261-5265 (2009-08-07)
Crystallography driven optimisation of a lead derived from similarity searching of the GSK compound collection resulted in the discovery of quinoline-3-carboxamides as highly potent and selective inhibitors of phosphodiesterase 4B. This series has been optimized to GSK256066, a potent PDE4B
Cathy J Tralau-Stewart et al.
The Journal of pharmacology and experimental therapeutics, 337(1), 145-154 (2011-01-06)
Oral phosphodiesterase (PDE) 4 inhibitors such as roflumilast have established the potential of PDE4 inhibition for the treatment of respiratory diseases. However, PDE4 inhibitor efficacy is limited by mechanism-related side effects such as emesis and nausea. Delivering the inhibitor by
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