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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
Molecular Formula C19H17ClN2O3
Molecular Weight 356.803
Charge 0
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
Gateways to clinical trials.
2005 Jun
Cytochrome P450 3A4 is the major enzyme responsible for the metabolism of laquinimod, a novel immunomodulator.
2005 Jun
Treatment with laquinimod reduces development of active MRI lesions in relapsing MS.
2005 Mar 22
Inhibition of the development of chronic experimental autoimmune encephalomyelitis by laquinimod (ABR-215062) in IFN-beta k.o. and wild type mice.
2006 Apr
Oral disease-modifying treatments for multiple sclerosis: the story so far.
2007
Novel oral agents for multiple sclerosis.
2007 May
Disease-modifying agents for multiple sclerosis: recent advances and future prospects.
2008
Evaluation of the effects of a new drug candidate (GEMSP) in a chronic EAE model.
2008 May 22
Review of teriflunomide and its potential in the treatment of multiple sclerosis.
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
Oral laquinimod therapy in relapsing multiple sclerosis.
2009 Jul
Recent advances in the treatment of amyotrophic lateral sclerosis. Emphasis on kynurenine pathway inhibitors.
2009 Mar
Promising treatments of tomorrow for multiple sclerosis.
2009 Oct
New oral drugs for multiple sclerosis.
2009 Oct
The future of multiple sclerosis therapy.
2009 Oct
Emerging therapies for treatment of multiple sclerosis.
2010
Multiple sclerosis therapies: molecular mechanisms and future.
2010
Risks vs benefits of glatiramer acetate: a changing perspective as new therapies emerge for multiple sclerosis.
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
Current and future role of interferon beta in the therapy of multiple sclerosis.
2010 Oct
Emerging therapies in relapsing-remitting multiple sclerosis.
2010 Sep
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 Sat Dec 16 17:39:21 GMT 2023
Edited
by admin
on Sat Dec 16 17:39:21 GMT 2023
Record UNII
908SY76S4G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LAQUINIMOD
INN   MI   WHO-DD  
INN  
Official Name English
TV-5600 FREE ACID
Code English
LAQUINIMOD [MI]
Common Name English
ABR-215062
Code English
Laquinimod [WHO-DD]
Common Name English
ABR-215062 FREE ACID
Code English
laquinimod [INN]
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS NERVENTRA (REFUSED: MULTIPLE SCLEROSIS)
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
WHO-VATC QN07XX10
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
NCI_THESAURUS C308
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
WHO-ATC N07XX10
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
Code System Code Type Description
MERCK INDEX
m6692
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY Merck Index
INN
8089
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
FDA UNII
908SY76S4G
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID30179536
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
DRUG BANK
DB06685
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
WIKIPEDIA
LAQUINIMOD
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
CAS
248281-84-7
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
DRUG CENTRAL
4825
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
NCI_THESAURUS
C76569
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL66092
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
SMS_ID
100000092997
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
PUBCHEM
54677946
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
EVMPD
SUB25236
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
MESH
C476223
Created by admin on Sat Dec 16 17:39:22 GMT 2023 , Edited by admin on Sat Dec 16 17:39:22 GMT 2023
PRIMARY
Related Record Type Details
ARYL HYDROCARBON RECEPTOR
TARGET -> ACTIVATOR
Structure of LAQUINIMOD SODIUM
SALT/SOLVATE -> PARENT
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of DESMETHYL-LAQUINIMOD
METABOLITE -> PARENT
Structure of 3-QUINOLINECARBOXAMIDE, 5-CHLORO-N-ETHYL-1,2-DIHYDRO-4-HYDROXY-N-(4-HYDROXYPHENYL)-1-METHYL-2-OXO-
METABOLITE -> PARENT
Related Record Type Details
Structure of LAQUINIMOD
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