| Identification | Back Directory | [Name]
CIVENTICHEM CV-4057 | [CAS]
248281-84-7 | [Synonyms]
LAQ
CS-82
ABR 215062
ABR-215062
Lanquinimod
CIVENTICHEM
oro-N-ethyL
-2-oxo-N-phenyL
ine-3-carboxamide
Laquinimod, >=98%
-1,2-dihydroquinoL
-4-hydroxy-1-methyL
CIVENTICHEM CV-4057
ABR-215062 (Laquinimod)
LaquiniMod (ABR-215062)
Laquinimod potassium salt
ABR215062; ABR 215062 (LAQUINIMOD)
LaquiniMod, SAIK-MS coMpound, ABR-215062
5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenylquinoline-3-carboxamide
5-Chloro-N-Et-4-hydroxy-1-methyl-2-oxo-N-Ph-1,2-dihydroquinoline-3-carboxamide
5-Chloro-4-hydroxy-1-methyl-2-oxo-N-ethyl-N-phenyl-1,2-dihydroquinoline-3-carboxamide
5-chloro-N-ethyl-4-hydroxy-1-Methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxaMide
3-Quinolinecarboxamide, 5-chloro-N-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-N-phenyl-
5-Chloro-4-hydroxy-1-Methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl-phenyl-aMide
LAQUINIMOD,5-CHLORO-4-HYDROXY-1-METHYL-2-OXO-1,2-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID ETHYL-PHENYL-AMIDE
LaquiniMod,CiventicheMCV-4057,5-Chloro-4-hydroxy-1-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylicacidethylphenylaMide | [EINECS(EC#)]
692-155-1 | [Molecular Formula]
C19H17ClN2O3 | [MDL Number]
MFCD08689859 | [MOL File]
248281-84-7.mol | [Molecular Weight]
356.8 |
| Chemical Properties | Back Directory | [Melting point ]
201 °C (decomp) | [Boiling point ]
484.8±45.0 °C(Predicted) | [density ]
1.395±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Soluble in DMSO (>25 mg/ml) | [form ]
solid | [pka]
4.50±1.00(Predicted) | [color ]
Off-white | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. |
| Hazard Information | Back Directory | [Description]
Laquinimod (248281-84-7) is an immunomodulator1 that inhibits inflammation2 and autoimmunity3,4 via activation of the aryl hydrocarbon receptor (AhR)5. It has been investigated as a treatment for multiple sclerosis6 and has shown efficacy in Huntington’s disease models7,8. | [Uses]
Laquinimod (ABR-215062), an orally available carboxamide derivative, is a potent immunomodulator which prevents neurodegeneration and inflammation in the central nervous system. Laquinimod reduces astrocytic NF-κB activation to protect from Cuprizone-induced demyelination. Laquinimod has?the?potential?for relapsing remitting (RR) and chronic progressive (CP) forms of multiple sclerosis (MS; RRMS or CPMS) as well as neurodegenerative diseases?research[1][2][3][4]. | [Definition]
ChEBI: Laquinimod is an aromatic amide. | [in vitro]
abr-215062 was shown to completely inhibit the development of murine acute experimental autoimmune encephalomyelitis (eae) [1]. | [in vivo]
abr-215062 dose-dependently inhibited disease and showed better disease inhibitory effects as compared to roquinimex (linomide). furthermore, abr-215062 inhibited the inflammation of both cd4+ t cells and macrophages into central nervous tissues [2]. | [IC 50]
NF-κB | [References]
J?nsson et al. (2004), Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders: Structure-Activity Relationship; Med. Chem. 47 2075
Rothhammer et al. (2021); Aryl Hydrocarbon Receptor Activation in Astrocytes by Laquinimod Ameliorates Autoimmune Inflammation in the CNS, Neurol. Neuroimmunol. Neuroinflamm., 8 e946
Pitarokoili et al. (2014), Laquinimod exerts strong clinical and immunomodulatory effects in Lewis rat experimental autoimmune neuritis; Neuroimmunol., 274 38
Ott et al. (2019), Laquinimod, a prototypic quinoline-3-carboxamide and aryl hydrocarbon receptor agonist, utilizes CD155-mediated natural killer/dendritic cell interaction to suppress CNS autoimmunity; Neuroinflammation, 16 49
Kaye et al. (2016), Laquinimod arrests experimental autoimmune encephalitis by activating the aryl hydrocarbon receptor; Natl. Acad. Sci. USA., 113 E6145
Th?ne and Linker (2016), Laquinimod in the treatment of multiple sclerosis: a review of the data so far; Drug Des. Devel. Ther., 10 1111
Dobson et al. (2016), Laquinimod dampens hyperactive cytokine production in Huntington’s disease patient myeloid cells; Neurochem., 137 782
Garcia-Miralles et al. (2016), Laquinimod rescues striatal, cortical and white matter pathology and results in modest behavioural improvements in the YAC128 model of Huntington disease; Rep., 6 31652 |
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