Paquinimod

Names

[ Name ]:
Paquinimod

[Synonym ]:
N-ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide
Paquinimod
N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide
Paquinimod [INN]
N-ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide
N-ethyl-N-phenyl-1,2-dihydro-5-ethyl-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide
UNII-HB76GLG27V

Biological Activity

[Description]:

Paquinimod is a S100A9 inhibitor, which prevents S100A9 binding to TLR-4.

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Toll-like Receptor (TLR)

Research Areas >> Metabolic Disease

Research Areas >> Inflammation/Immunology

[Target]

S100A9[1]

[In Vivo]

S100A9 is a calcium-binding protein of the S100 family. Paquinimod is an immunomodulatory compound preventing S100A9 binding to TLR-4. Prophylactic treatment with S100A9 inhibitor Paquinimod reduces pathology in experimental collagenase-induced osteoarthritis[1]. Paquinimod is a potent inhibitor of insulitis and diabetes development in the NOD mouse. To assess the preventive efficacy of Paquinimod on diabetes development in female NOD mice, groups of mice are treated with daily doses of 0.04, 0.2, 1, and 5 mg/kg/day of Paquinimod from week 10 of age until week 20 of age. Glycosuria is analyzed on a weekly basis from 10 weeks of age until the endpoint of the experiment at 40 weeks of age. There is a clear dose-dependent reduction in diabetes development in the Paquinimod-treated mice[2].

[Animal admin]

Mice[2] Female NOD/MrkTac mice are exposed to increasing concentration of CO2 and upon loss of consciousness euthanized by cervical dislocation. To investigate the effect of the Q-compound Paquinimod on development of glycosuria and insulitis, mice are treated with Paquinimod dissolved in drinking water at different concentrations corresponding to daily doses of about 0.04, 0.2, 1, and 5 mg/kg body weight/day). The mice are treated with Paquinimod starting from either 10 or 15 weeks of age. The duration of treatment varies from 5 to 23 weeks in the different experiments performed[2].

[References]

[1]. Schelbergen RF, et al. Prophylactic treatment with S100A9 inhibitor paquinimod reduces pathology in experimental collagenase-induced osteoarthritis. Ann Rheum Dis. 2015 Dec;74(12):2254-8.

[2]. Tahvili S, et al. Paquinimod prevents development of diabetes in the non-obese diabetic (NOD) mouse. PLoS One. 2018 May 9;13(5):e0196598.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.267g/cm3

[ Boiling Point ]:
487.259ºC at 760 mmHg

[ Molecular Formula ]:
C₂₁H₂₂N₂O₃

[ Molecular Weight ]:
350.41100

[ Flash Point ]:
248.486ºC

[ Exact Mass ]:
350.16300

[ PSA ]:
62.54000

[ LogP ]:
3.47320

[ Vapour Pressure ]:
0mmHg at 25°C

[ Index of Refraction ]:
1.648

[ Storage condition ]:
2-8℃

Paquinimod

Names

Biological Activity

Chemical & Physical Properties

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream