An immunomodulator
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Laquinimod

Item No. 24187

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-chloro-N-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinolinecarboxamide
CAS Number
248281-84-7
Synonyms
  • ABR-215062
Molecular Formula
C19H17ClN2O3
Formula Weight
356.8
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 10 mg/mlEthanol: 2 mg/ml
λmax
205, 239, 303 nm
SMILES
ClC1=C(C(O)=C(C(N(CC)C2=CC=CC=C2)=O)C(N3C)=O)C3=CC=C1
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
InChi Key
GKWPCEFFIHSJOE-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Laquinimod is an orally bioavailable immunomodulator.1 It induces expression of genes related to antigen presentation and inflammatory pathways in human peripheral blood mononuclear cells (PBMCs) when used at a concentration of 0.1 μM.2 In a mouse model of acute autoimmune encephalomyelitis (aEAE), laquinimod (5 mg/kg per day) decreases the severity of symptoms by 91.4%, and it decreases the number of relapses in a mouse model of chronic EAE (crEAE).1 It decreases T cell and macrophage density and demyelination in the spinal cord of EAE mice compared to non-treated controls when administered at a dose of 5 mg/kg per day.3 Laquinimod (12.5 and 25 mg/kg per day) decreases inflammatory lesions and demyelination in the sciatic nerve in a rat model of experimental autoimmune neuritis (EAN).4 Laquinimod (25 mg/kg per day) activates gene expression in the aryl hydrocarbon receptor (AhR) pathway in splenocytes from EAE mice with no effect in AhR knockout mice.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brunmark, C., Runström, A., Ohlsson, L., et al. The new orally active immunoregulator laquinimod (ABR-215062) effectively inhibits development and relapses of experimental autoimmune encephalomyelitis. J. Neuroimmunol. 130(1-2), 163-172 (2002).

    2. Gurevich, M., Gritzman, T., Orbach, R., et al. Laquinimod suppress antigen presentation in relapsing-remitting multiple sclerosis: in-vitro high-throughput gene expression stud. J. Neuroimmunol. 221(1-2), 87-94 (2010).

    3. Wegner, C.D., Stadelmann, C., Pförtner, R., et al. Laquinimod interferes with migratory capacity of T cells and reduces IL-17 levels, inflammatory demyelination and acute axonal damage in mice with experimental autoimmune encephalomyelitis. J. Neuroimmunol. 227(1-2), 133-143 (2010).

    4. Pitarokoili, K., Ambrosius, B., Schrewe, L., et al. Laquinimod exerts strong clinical and immunomodulatory effects in Lewis rat experimental autoimmune neuritis. J. Neuroimmunol. 274(1-2), 38-45 (2014).

    5. Kaye, J., Piryatinsky, V., Birnberg, T., et al. Laquinimod arrests experimental autoimmune encephalomyelitis by activating the aryl hydrocarbon receptor. Proc. Natl. Acad. Sci. USA 113(41), E6145-E6152 (2016).