801312-28-7

Basic information

• Product Name: 6-[[3-[(Dimethylamino)carbonyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methyl-3-quinolinecarboxamide
• Synonyms: 6-[[3-[(Dimethylamino)carbonyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methyl-3-quinolinecarboxamide;GSK-256066;GSK2606416;6-(3-(dimethylcarbamoyl)phenylsulfonyl)-4-(3-methoxyphenylamino)-8-methylquinoline-3-carboxamide;6-[[3-[(Dimethylamino)carbonyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methyl-3-quinolinecarboxamide GSK-256066;6-(3-(Dimethylcarbamoyl)phenylsulfonyl)-4-(3-methoxyphenylamino)-8-methylquinoline-3-carboxami
• CAS NO: 801312-28-7
• Molecular Formula: C27H26N4O5S
• Molecular Weight: 518.58414
• Product Categories: Inhibitor;Inhibitors
• Mol File: 801312-28-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 791.685 °C at 760 mmHg
• Flash Point: 432.596 °C
• Appearance: /
• Density: 1.345
• Solubility: insoluble in DMSO; insoluble in EtOH; insoluble in H2O
• PKA: 15.01±0.30(Predicted)
• CAS DataBase Reference: 6-[[3-[(Dimethylamino)carbonyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methyl-3-quinolinecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[[3-[(Dimethylamino)carbonyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methyl-3-quinolinecarboxamide(801312-28-7)
• EPA Substance Registry System: 6-[[3-[(Dimethylamino)carbonyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methyl-3-quinolinecarboxamide(801312-28-7)

Safety Data

• Hazardous Substances Data: 801312-28-7(Hazardous Substances Data)

Usage

Uses

Quinoline derivative and a potential selective PDE4 phosphodiesterase inhibitor to treat prophylaxis or treatment of clinical conditions such as inflammatory or allergic diseases.

Biological Activity

apparent ic50 3.2 pm, steady state ic50 < 0.5 pmgsk256066 is an exceptionally high-affinity and selective inhibitor of pde4 designed for inhaled delivery.oral phosphodiesterase (pde) 4 inhibitors have demonstrated clinical efficacy in chronic obstructive pulmonary disease and asthma.

in vitro

gsk256066 is a slow- and tight-binding inhibitor of pde4b, more potent than any previously documented compound, for example roflumilast, tofimilast and cilomilast [1].

in vivo

when administered by the intratracheal route to rats, gsk256066 inhibited lps-induced pulmonary neutrophilia with ed50s of 1.1 μg/kg (aqueous suspension) and 2.9 μg/kg (dry powder formulation) and was more potent than an aqueous suspension of the corticosteroid fluticasone propionate (ed50 9.3 μg/kg) [1].

references

[1] tralau-stewart cj, williamson ra, nials at, gascoigne m, dawson j, hart gj, angell ad, solanke ye, lucas fs, wiseman j, ward p, ranshaw le, knowles rg. gsk256066, an exceptionally high-affinity and selective inhibitor of phosphodiesterase 4 suitable for administration by inhalation: in vitro, kinetic, and in vivo characterization. j pharmacol exp ther. 2011;337(1):145-54. [2] watz h, mistry sj, lazaar al; ipc101939 investigators. safety and tolerability of the inhaled phosphodiesterase 4 inhibitor gsk256066 in moderate copd. pulm pharmacol ther. 2013;26(5):588-95.

InChI: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)

Upstream product

• 801312-98-1 6-({3-[(dimethylamino)carbonyl]phenyl}thiol)-8-methyl-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamide 

Relevant articles and documents

QUINOLINE DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS

There are provided according to the invention novel compounds of formula (I) or pharmaceutically acceptable salts thereof, wherein R1, R2, R19, R20 and R34 are as described in the specification, processes for preparing them, formulations containing them and their use in therapy for the treatment of inflammatory diseases.