Laquinimod

Names

[ Name ]:
Laquinimod

[Synonym ]:
5-Chloro-N-Et-4-hydroxy-1-methyl-2-oxo-N-Ph-1,2-dihydroquinoline-3-carboxamide
5-chloro-N-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinolinecarboxamide
5-CHLORO-N-ETHYL-4-HYDROXY-1-METHYL-2-OXO-N-PHENYL-1,2-DIHYDROQUINOLINE-3-CARBOXAMIDE
5-chloro-n-ethyl-2-hydroxy-1-methyl-4-oxo-n-phenyl-1,4-dihydroquinoline-3-carboxamide
5-Chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl-phenyl-amide
Lanquinimod
Laquinimod
2-{[(2,4-Dichlorophenoxy)acetyl]amino}ethyl thiocyanate
N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide
Thiocyanic acid, 2-[[2-(2,4-dichlorophenoxy)acetyl]amino]ethyl ester
5-chloro-1,2-dihydro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinoline carboxamide
5-Chloro-4-hydroxy-1-methyl-2-oxo-N-ethyl-N-phenyl-1,2-dihydroquinoline-3-carboxamide
N-ethyl-N-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide
[14C]-Laquinimod
ABR-215062

Biological Activity

[Description]:

Laquinimod is a potent immunomodulator which prevents neurodegeneration and inflammation in the central nervous system.

[Related Catalog]:

Signaling Pathways >> NF-κB >> NF-κB

Research Areas >> Inflammation/Immunology

[Target]

NF-κB

[In Vitro]

Laquinimod reverses EAE and inhibits pathogenic T cell immune responses. Laquinimod reverses RR-EAE and inhibits inflammatory T cell responses via a direct effect on myeloid APC. Laquinimod alters myeloid APC subsets and inhibits Th1 and Th17 polarization of myelin-specific T cells. Laquinimod-induced type II (M2) monocytes reverse established EAE[1]. Laquinimod modulates the phenotype of B cells of healthy donors. Laquinimod modulates expression of markers related to regulatory capacity in B cells of RRMS patients. Laquinimod reduces IFNγ cytokine expression in CD4+ T cells[2].

[In Vivo]

Laquinimod treatment inhibits donor myelin-specific T cells from transferring EAE to naive recipient mice. In vivo laquinimod treatment alters subpopulations of myeloid antigen presenting cells (APC) that include a decrease in CD11c+CD11b+CD4+ dendritic cells (DC) and an elevation of CD11bhiGr1hi monocytes[1].

[Cell Assay]

Purified CD11b+ cells from laquinimod- or vehicle-treated mice are cultured with naive CD4+ cells isolated from laquinimod- or vehicle-treated 2D2 mice and antigen (MOG p35-55, 20 µg/mL). Cells are cultured in 96-well microtitre plates at a concentration of 0.25×106 cells/mL. Culture medium consisted of RPMI 1640 supplemented with L-glutamine (2 mM), sodium pyruvate (1 mM), penicillin (100 U/mL), streptomycin (0.1 mg/mL), 2-mercaptoethanol (5×10-5 M) and 10% (v/v) fetal bovine serum. Cells are incubated for 48 h and pulsed for 18 h with 1 µCi per well of [3H]-thymidine before harvesting.

[Animal admin]

Seven to 10-week-old female C57BL/6, DBA/1 or SJL/J mice are injected subcutaneously with 50 µg MOG p35-55, 50 µg rMOG or 100 µg PLP p139-151, respectively, in complete Freund's adjuvant. After immunization and 2 days later, mice receive 200 ng (C57BL/6) or 100 ng (SJL/J) pertussis toxin intraperitoneally (i.p.). For adoptive transfer, donor SJL/J mice are immunized as described above and treated daily with laquinimod or vehicle. 10 days later, cells from draining lymph nodes and spleen are isolated, re-stimulated for 48 h (20 µg/mL PLP p139-151), and injected i.p. into naive SJL/J recipients (107 cells per mouse). Animals are observed daily and clinical scores are assessed as follows: 0, no signs; 1, decreased tail tone; 2, mild monoparesis or paraparesis; 3, severe paraparesis; 4, paraplegia and/or quadraparesis; and 5, moribund or death.

[References]

[1]. Schulze-Topphoff, Ulf., et al. Laquinimod, a quinoline-3-carboxamide, induces type II myeloid cells that modulate central nervous system autoimmunity. PLoS One (2012), 7(3), e33797.

[2]. Toubi E, et al. Laquinimod modulates B cells and their regulatory effects on T cells in Multiple Sclerosis. J Neuroimmunol. 2012 Oct 15;251(1-2):45-54.

[3]. Brück W, et al. Reduced astrocytic NF-κB activation by laquinimod protects from cuprizone-induced demyelination. Acta Neuropathol. 2012 Sep;124(3):411-24.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
546.0±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₉H₁₇ClN₂O₃

[ Molecular Weight ]:
356.80

[ Flash Point ]:
284.0±30.1 °C

[ PSA ]:
87.42000

[ LogP ]:
2.79

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.587

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
T+

[ 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%

Related Compounds

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