| Size | Price | Stock | Qty |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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Purity: ≥98%
Laquinimod (also known as ABR-215062, LAQ) is a potent and orally bioactive immunoregulator that is being studied as a potential MS treatment. The primary animal model for the investigation of multiple sclerosis (MS) is experimental autoimmune encephalomyelitis (EAE), an inflammatory autoimmune disease of the CNS that can be induced in rodents. Peripheral blood mononuclear cells (PBMC) are unaffected by laquinimod treatment at concentrations of 0.1 to 1 μM. Laquinimod is demonstrated to induce suppression of genes associated with antigen presentation and associated inflammatory pathways using the large-scale gene expression microarray analysis in PBMC from healthy subjects or relapsing-remitting multiple sclerosis (RRMS) patients.
| Targets |
NF-κB
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|---|---|
| ln Vitro |
Laquinimod inhibits pathogenic T cell immune responses and reverses EAE. Through a direct impact on myeloid APC, laquinimod treats RR-EAE and prevents inflammatory T cell responses. Inhibiting Th1 and Th17 polarization of myelin-specific T cells is one of laquinimod's effects on myeloid APC subsets. The established EAE is reversed by type II (M2) monocytes induced by laquinimod[1]. B cells from healthy donors have their phenotype altered by laquinimod. In B cells from RRMS patients, laquinimod modifies the expression of markers for regulatory capacity. IFNγ cytokine expression is decreased by laquinimod in CD4+ T cells[2].
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| ln Vivo |
Laquinimod treatment prevents the transmission of EAE to naive recipient mice by donor myelin-specific T cells. The in vivo laquinimod treatment changes the CD11c+CD11b+CD4+ dendritic cells (DC) and CD11bhiGr1hi monocyte subpopulations of myeloid antigen presenting cells (APC)[1].
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| Cell Assay |
Purified CD11b+ cells from mice treated with laquinimod or a vehicle are cultured with naive CD4+ cells from mice treated with laquinimod or a vehicle and antigen (MOG p35-55, 20 g/mL). At a density of 0.25×106 cells/mL, cells are cultured in 96-well microtitre plates. A RPMI 1640-based culture medium 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 served as the culture medium. Before being harvested, cells are first incubated for 48 hours and then pulsed for 18 hours with 1 µCi of [3H]-thymidine per well.
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| Animal Protocol |
Female C57BL/6, DBA/1, or SJL/J mice aged seven to ten weeks receive subcutaneous injections of 50 µg MOG p35-55, 50 g rMOG, or 100 µg PLP p139-151, respectively, all dissolved in complete Freund's adjuvant. Mice are given either 200 ng (C57BL/6) or 100 ng (SJL/J) of pertussis toxin intraperitoneally (i.p.) after vaccination and two days later. Donor SJL/J mice are treated daily with laquinimod or a vehicle and immunized as previously mentioned. 10 days later, 107 cells per mouse are administered intravenously to naive SJL/J recipients after being isolated from draining lymph nodes and the spleen and re-stimulated for 48 hours (20 g/mL PLP p139-151). Animals are observed every day, and the following clinical scores are calculated: 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.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Hepatic. Cytochrome P450 3A4 is the major enzyme responsible for the metabolism of laquinimod. Laquinimod has known human metabolites that include 5-chloro-N-ethyl-4,7-dihydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide, 5-chloro-N-ethyl-4,8-dihydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide, 5-chloro-N-ethyl-4,6-dihydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide, 5-chloro-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide, 5-chloro-N-ethyl-4-hydroxy-N-(4-hydroxyphenyl)-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide, and 5-chloro-N-ethyl-4-hydroxy-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide. |
| References |
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| Additional Infomation |
Laquinimod is an aromatic amide.
Laquinimod is an immunomodulator developed by Active Biotech and produced by Teva Pharmaceutical Industries. It is currently under development in phase III trials for treatment of multiple sclerosis as an oral therapy, like fingolimod. It has been shown to reduce disease activity on magnetic resonance imaging and to be well tolerated orally. Drug Indication Investigated for use/treatment in multiple sclerosis. Treatment of multiple sclerosis |
| Molecular Formula |
C19H17CLN2O3
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|---|---|---|
| Molecular Weight |
356.8
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| Exact Mass |
356.09
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| Elemental Analysis |
C, 63.96; H, 4.80; Cl, 9.94; N, 7.85; O, 13.45
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| CAS # |
248281-84-7
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| Related CAS # |
Laquinimod sodium;248282-07-7
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| PubChem CID |
54677946
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
546.0±50.0 °C at 760 mmHg
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| Flash Point |
284.0±30.1 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.587
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| LogP |
2.79
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
25
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| Complexity |
571
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC1=C([H])C([H])=C([H])C2=C1C(=C(C(N(C1C([H])=C([H])C([H])=C([H])C=1[H])C([H])([H])C([H])([H])[H])=O)C(N2C([H])([H])[H])=O)O[H]
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| InChi Key |
GKWPCEFFIHSJOE-UHFFFAOYSA-N
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| InChi Code |
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
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| Chemical Name |
5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenylquinoline-3-carboxamide
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.01 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 2: 30% Propylene glycol , 5% Tween 80 , 65% D5W: 30 mg/mL (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8027 mL | 14.0135 mL | 28.0269 mL | |
| 5 mM | 0.5605 mL | 2.8027 mL | 5.6054 mL | |
| 10 mM | 0.2803 mL | 1.4013 mL | 2.8027 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT02215616 | Completed | Drug: Laquinimod Drug: Placebo |
Huntington's Disease | Teva Branded Pharmaceutical Products R&D, Inc. |
October 28, 2014 | Phase 2 |
| NCT05187403 | Completed | Drug: Laquinimod Drug: Placebo |
Eye Diseases | Active Biotech AB | December 9, 2021 | Phase 1 |
| NCT02085863 | Completed | Drug: laquinimod Drug: Placebo |
Pharmacokinetics Pharmacodynamics |
Teva Branded Pharmaceutical Products R&D, Inc. |
February 2014 | Phase 1 |
| NCT01085084 | Completed | Drug: Laquinimod Drug: Placebo |
Lupus Arthritis | Teva Branded Pharmaceutical Products R&D, Inc. |
October 4, 2010 | Phase 2 |
| NCT02215616 | Completed | Drug: Laquinimod Drug: Placebo |
Huntington's Disease | Teva Branded Pharmaceutical Products R&D, Inc. |
October 28, 2014 | Phase 2 |
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