CAS Number248281-84-7
Synonyms5-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-et
Molecular FormulaC19H17ClN2O3
Molecular Weight356.80
Purity≥98 (HPLC)%
Density1.4±0.1 g/cm3
Boiling Point546.0±50.0 °C at 760 mmHg
Appearancepowder
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 248281-84-7 |
| Catalog No. | 2A-9060337 |
| Chinese Name | 拉喹莫德 |
| Synonyms | 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-et |
| Molecular Formula | C19H17ClN2O3 |
| Molecular Weight | 356.80 |
| Purity | ≥98 (HPLC) |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 546.0±50.0 °C at 760 mmHg |
| Appearance | powder |
| Storage Condition | Store under inert gas; avoid air |
| Application | Laquinimod is a potent immunomodulator that prevents neurodegeneration and inflammation in the central nervous system. |
| HTC | 2933790090 |
| MDL Number | MFCD08689859 |
| SMILES | OC(C1=C(C=CC=C1N(C2=O)C)Cl)=C2C(N(C3=CC=CC=C3)CC)=O |
| InChI | 1S/C19H17ClN2O3/c1-3-22(12-8-5-4-6-9-12)19(25)16-17(23)15-13(20)10-7-11-14(15)21(2)18(16)24/h4-11,23H,3H2,1-2H3 |
| InChI Key | GKWPCEFFIHSJOE-UHFFFAOYSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| MSDS | msds/60337_1_248281_84_7.pdf |
| Bioactivity | 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. 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 InChIKey GKWPCEFFIHSJOE-UHFFFAOYSA-N SMILES CCN(C(=O)c1c(O)c2c(Cl)cccc2n(C)c1=O)c1ccccc1 |
| Use of | Laquinimod is a potent immunomodulator which prevents neurodegeneration and inflammation in the central nervous system. Properties Name 5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenylquinoline-3-carboxamide Synonym More Synonyms Laquinimod 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 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]. 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. Chemical & Physical Properties PSA 87.42000 Index of Refraction 1.587 InChIKey GKWPCEFFIHSJOE-UHFFFAOYSA-N |
| Tax Rebate | 9.0% |
| Supervision | None MFN tariff: 9.0% Ordinary tariff: 20.0% |
| Transport Info | Product name: Summary 2933790090. other lactams. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:9.0%. General tariff:20.0% |
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