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Details

Stereochemistry ACHIRAL
Molecular Formula C27H26N4O5S
Molecular Weight 518.584
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GSK-256066

SMILES

COC1=CC(NC2=C(C=NC3=C(C)C=C(C=C23)S(=O)(=O)C4=CC=CC(=C4)C(=O)N(C)C)C(N)=O)=CC=C1

InChI

InChIKey=JFHROPTYMMSOLG-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C27H26N4O5S
Molecular Weight 518.584
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

GSK-256066 is a PDE4B inhibitor which was developed by GlaxoSmithKline and tested in phase II of clinical trials for the treatment of COPD, Asthma and Seasonal allergic rhinitis. According to the GSK pipeline, development of GSK-256066 was terminated. There are studies that describes the possibility of repurposing of the drug as antitrypanosomal agents, because it inhibits PDEB1 of Trypanosoma brucei.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.2 pM [IC50]
10.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Curative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
18.3 pg/mL
87.5 μg single, respiratory
GSK-256066 plasma
Homo sapiens
17.3 pg/mL
8.75 μg 1 times / day multiple, respiratory
GSK-256066 plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
36.8 pg × h/mL
87.5 μg single, respiratory
GSK-256066 plasma
Homo sapiens
64.8 pg × h/mL
8.75 μg 1 times / day multiple, respiratory
GSK-256066 plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
COPD: 25 or 87.5 mcg should be inhaled once daily. Asthma: patients receive inhaled drug at a dose of 87.5 mcg once per day.
Route of Administration: Other
In Vitro Use Guide
LPS-stimulated TNFalpha expression was inhibited in PBMCs and whole blood using 10(-4)-10 nM of GSK-256066.
Substance Class Chemical
Record UNII
2D6GK059SR
Record Status Validated (UNII)
Record Version