Roquinimex

Names

[ Name ]:
Roquinimex

[Synonym ]:
Roquinimex
LS-2616
1,2-Dihydro-4-hydroxy-N,1-dimethyl-2-oxo-N-phenyl-3-quinolinecarboxamide
4-Hydroxy-N,1-dimethyl-2-oxo-N-phenyl-1,2-dihydro-3-quinolinecarboxamide
FCF-89
Linomide
4-hydroxy-N,1-dimethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
N-phenyl-N-methyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide
3-Quinolinecarboxamide, 1,2-dihydro-4-hydroxy-N,1-dimethyl-2-oxo-N-phenyl-
N-phenyl-N-methyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide

Biological Activity

[Description]:

Roquinimex (Linomide; PNU212616; ABR212616) is a quinoline derivative immunostimulant which increases NK cell activity and macrophage cytotoxicity; inhibits angiogenesis and reduces the secretion of TNF alpha.IC50 value:Target: TNF alphaProphylactic administration of DSS-treated mice with roquinimex significantly reduced clinical signs of colitis, MDS and the CH-reduction. Moreover, in roquinimex treated animals, the MPO activity was significantly reduced by more than 50% compared to DSS control mice. Notably, therapeutic administration of roquinimex in DSS-treated mice also significantly inhibited the MDS, CH-reduction and MPO activity [2]. Linomide, a synthetic immunomodulator, at concentrations effective in vivo reduces the number of MBP-reactive TNF-alpha and increases MBP-reactive IL-10 and TGF-beta mRNA expressing MNC from MS patients' blood when analysed in vitro. Compared to dexamethasone, Linomide up-regulated levels of blood MNC expressing mRNA of TGF-beta after culture in presence of MBP [3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> TNF Receptor

Natural Products >> Alkaloid

Research Areas >> Inflammation/Immunology

[References]

[1]. Roquinimex, From Wikipedia

[2]. Liu Q, et al. Roquinimex inhibits dextran sodium sulfate-induced murine colitis. Inflamm Res. 2003 Feb;52(2):64-8.

[3]. Tian WZ, et al. Linomide (roquinimex) affects the balance between pro- and anti-inflammatory cytokines in vitro in multiple sclerosis. Acta Neurol Scand. 1998 Aug;98(2):94-101.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
436.2±45.0 °C at 760 mmHg

[ Melting Point ]:
204 °C(dec.)

[ Molecular Formula ]:
C₁₈H₁₆N₂O₃

[ Molecular Weight ]:
308.331

[ Flash Point ]:
217.6±28.7 °C

[ Exact Mass ]:
308.116089

[ PSA ]:
62.54000

[ LogP ]:
1.65

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.686

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36/37

[ RIDADR ]:
UN 2811

[ HS Code ]:
2933790090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933790090

[ Summary ]:
2933790090. other lactams. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:9.0%. General tariff:20.0%