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Details

Stereochemistry ACHIRAL
Molecular Formula C19H16ClN2O3.Na
Molecular Weight 378.785
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAQUINIMOD SODIUM

SMILES

[Na+].CCN(C(=O)C1=C([O-])C2=C(C=CC=C2Cl)N(C)C1=O)C3=CC=CC=C3

InChI

InChIKey=JWHPPWBIIQMBQC-UHFFFAOYSA-M
InChI=1S/C19H17ClN2O3.Na/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;/q;+1/p-1

HIDE SMILES / InChI
Molecular Formula C19H16ClN2O3
Molecular Weight 355.795
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/27089834 | https://www.vidal.ru/drugs/nerventra__40726

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
661
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Nerventra

Approved Use

http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002546/WC500171788.pdf

Launch Date

2013
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Lupus nephritis
6
Sources: DOI: 10.1136/annrheumdis-2013-eular.528
 Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Suppression of experimental autoimmune neuritis by ABR-215062 is associated with altered Th1/Th2 balance and inhibited migration of inflammatory cells into the peripheral nerve tissue.
2002 Apr
The new orally active immunoregulator laquinimod (ABR-215062) effectively inhibits development and relapses of experimental autoimmune encephalomyelitis.
2002 Sep
Gateways to clinical trials.
2004 Jan-Feb
Laquinimod (ABR-215062) suppresses the development of experimental autoimmune encephalomyelitis, modulates the Th1/Th2 balance and induces the Th3 cytokine TGF-beta in Lewis rats.
2004 Nov
[Future possibilities of the multiple sclerosis treatment].
2005
Cytochrome P450 3A4 is the major enzyme responsible for the metabolism of laquinimod, a novel immunomodulator.
2005 Jun
Oral laquinimod for treatment of relapsing-remitting multiple sclerosis.
2008 Aug
Effect of laquinimod on MRI-monitored disease activity in patients with relapsing-remitting multiple sclerosis: a multicentre, randomised, double-blind, placebo-controlled phase IIb study.
2008 Jun 21
Laquinimod, a new oral drug for multiple sclerosis.
2008 Jun 21
Evaluation of the effects of a new drug candidate (GEMSP) in a chronic EAE model.
2008 May 22
Emerging oral drugs for multiple sclerosis.
2008 Sep
Kynurenine pathway metabolites in humans: disease and healthy States.
2009
Identification of human S100A9 as a novel target for treatment of autoimmune disease via binding to quinoline-3-carboxamides.
2009 Apr 28
Recent developments in multiple sclerosis therapeutics.
2009 Dec 7
New oral disease-modifying therapies for multiple sclerosis.
2009 May 8
Promising treatments of tomorrow for multiple sclerosis.
2009 Oct
Emerging therapies for treatment of multiple sclerosis.
2010
Multiple sclerosis therapies: molecular mechanisms and future.
2010
Multiple sclerosis: a supplement on the disease state, current therapies, and investigational treatments.
2010 Apr
Risks vs benefits of glatiramer acetate: a changing perspective as new therapies emerge for multiple sclerosis.
2010 Apr 15
Laquinimod suppress antigen presentation in relapsing-remitting multiple sclerosis: in-vitro high-throughput gene expression study.
2010 Apr 15
A novel probiotic mixture exerts a therapeutic effect on experimental autoimmune encephalomyelitis mediated by IL-10 producing regulatory T cells.
2010 Feb 2
Optimizing the benefit of multiple sclerosis therapy: the importance of treatment adherence.
2010 Feb 4
Emerging multiple sclerosis oral therapies.
2010 Jan 5
Identification of targets and new developments in the treatment of multiple sclerosis--focus on cladribine.
2010 Jul 21
New drug therapies for multiple sclerosis.
2010 Jun
Laquinimod, a new oral autoimmune modulator for the treatment of relapsing-remitting multiple sclerosis.
2010 May
Oral laquinimod in patients with relapsing-remitting multiple sclerosis: 36-week double-blind active extension of the multi-centre, randomized, double-blind, parallel-group placebo-controlled study.
2010 Nov
New approaches in the management of multiple sclerosis.
2010 Nov 24
Current and future role of interferon beta in the therapy of multiple sclerosis.
2010 Oct
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.
2010 Oct 8
Will the newer oral MS agents be welcomed by managed care organizations?
2010 Sep
Emerging oral agents for multiple sclerosis.
2010 Sep
Treatment options for multiple sclerosis: current and emerging therapies.
2010 Sep
Emerging therapies in relapsing-remitting multiple sclerosis.
2010 Sep
Emerging oral treatments in multiple sclerosis - clinical utility of cladribine tablets.
2010 Sep 7
Disease-modifying therapies in relapsing-remitting multiple sclerosis.
2010 Sep 7
Placebo-controlled trial of oral laquinimod for multiple sclerosis.
2012 Mar 15
Patents

Patents

06875869
2
07560557
2
07884208
2
08252933
2
08354428
2
08552194
2
08647646
2
08673322
2
JP2013544887A
2

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:12:20 GMT 2023
Edited
by admin
on Fri Dec 15 16:12:20 GMT 2023
Record UNII
4H914M0CSP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LAQUINIMOD SODIUM
USAN   WHO-DD  
USAN  
Official Name English
Sodium 5-chloro-3-(ethylphenylcarbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-olate
Systematic Name English
LAQUINIMOD SODIUM [USAN]
Common Name English
LAQUINIMOD SODIUM SALT [MI]
Common Name English
ABR-215062 SODIUM
Code English
NERVENTRA
Brand Name English
3-QUINOLINECARBOXAMIDE, 5-CHLORO-N-ETHYL-1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-N-PHENYL-, SODIUM SALT
Systematic Name English
LAQUINIMOD SODIUM SALT
MI  
Common Name English
Laquinimod sodium [WHO-DD]
Common Name English
TV-5600
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 466114
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
NCI_THESAURUS C308
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
EMA ASSESSMENT REPORTS NERVENTRA (REFUSED: MULTIPLE SCLEROSIS)
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL66092
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
FDA UNII
4H914M0CSP
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
MERCK INDEX
m6692
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID50179538
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
SMS_ID
100000156564
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
EVMPD
SUB130487
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
USAN
TT-103
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
PUBCHEM
23697158
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
CAS
248282-07-7
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
NCI_THESAURUS
C76693
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
DRUG BANK
DBSALT001816
Created by admin on Fri Dec 15 16:12:20 GMT 2023 , Edited by admin on Fri Dec 15 16:12:20 GMT 2023
PRIMARY
Related Record Type Details
Structure of LAQUINIMOD
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of LAQUINIMOD
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