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Details

Stereochemistry ACHIRAL
Molecular Formula C19H17ClN2O3
Molecular Weight 356.803
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAQUINIMOD

SMILES

CCN(C(=O)C1=C(O)C2=C(C=CC=C2Cl)N(C)C1=O)C3=CC=CC=C3

InChI

InChIKey=GKWPCEFFIHSJOE-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Laquinimod is a new orally available carboxamide derivative, which is currently developed for relapsing remitting (RR) and chronic progressive (CP) forms of multiple sclerosis (MS; RRMS or CPMS) as well as neurodegenerative diseases. The mechanism of action of laquinimod is not fully elucidated because the molecular target is not known. Treatment with laquinimod led to a significant and persistent increase in brain-derived neuroprotective factor (BDNF) serum levels compared to placebo treatment. In human studies, a decrease of pro-inflammatory and an increase of anti-inflammatory cytokines have been measured. After commercial launch the unexpected severe cardiac adverse events (AEs) such as serositis, pericarditis, and myocardial infarction were detected.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nerventra
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
0.6 mg once daily
Route of Administration: Oral
In Vitro Use Guide
Laquinimod, at concentrations of 5 to 3000 M, was incubated for 20 min with human liver microsomes. The metabolite formation exhibited, in general, single-enzyme Michaelis-Menten kinetics with Km in the range 0.09 to 1.9 mM and Vmax from 22 to 120 pmol/mg/min.