LAQUINIMOD SODIUM

Possibly Marketed Outside US

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 Search

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	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

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

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15764719	Substrate 661
inflammatory response 47 Target ID: GO:0006954 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27042003 / https://www.ncbi.nlm.nih.gov/pubmed/27089834	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Relapsing-remitting multiple sclerosis 8 Sources: https://www.vidal.ru/drugs/nerventra__40726	Primary	Approved 8583	Nerventra Approved Use http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002546/WC500171788.pdf Launch Date 2013
Crohn's disease 64 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25281416	Primary	Phase II 1147	Unknown Approved Use Unknown
Huntington's disease 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27296315	Primary	Phase II 1147	Unknown Approved Use Unknown
Lupus nephritis 7 Sources: DOI: 10.1136/annrheumdis-2013-eular.528	Primary	Phase II 1147	Unknown Approved Use Unknown
Lupus arthritis 2 Sources: https://www.google.ch/patents/US20130184310	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1826.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28859672/	2.7 mg 1 times / day steady-state, oral dose: 2.7 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
380.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29786964/	0.6 mg 1 times / day multiple, oral dose: 0.6 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
749.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29786964/	1.2 mg single, oral dose: 1.2 mg route of administration: Oral experiment type: SINGLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
107 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32237115/	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
99.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32237115/	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered: KETOCONAZOLE	KETOCONAZOLE	LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
115 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32237115/	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
123.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32237115/	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered: RIFAMPIN	RIFAMPIN	LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
376 ng/mL EXPERIMENT https://academic.oup.com/ecco-jcc/article/8/Supplement_1/S226/369200?login=true	0.5 mg 1 times / day multiple, oral dose: 0.5 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status:
885 ng/mL EXPERIMENT https://academic.oup.com/ecco-jcc/article/8/Supplement_1/S226/369200?login=true	1.5 mg 1 times / day multiple, oral dose: 1.5 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1447 ng/mL EXPERIMENT https://academic.oup.com/ecco-jcc/article/8/Supplement_1/S226/369200?login=true	2 mg 1 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
35275 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28859672/	2.7 mg 1 times / day steady-state, oral dose: 2.7 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7559 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29786964/	0.6 mg 1 times / day multiple, oral dose: 0.6 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
14872 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29786964/	1.2 mg single, oral dose: 1.2 mg route of administration: Oral experiment type: SINGLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
7140.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32237115/	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
21694 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32237115/	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered: KETOCONAZOLE	KETOCONAZOLE	LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
7368.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32237115/	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1497.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32237115/	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered: RIFAMPIN	RIFAMPIN	LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6996 ng × h/mL EXPERIMENT https://academic.oup.com/ecco-jcc/article/8/Supplement_1/S226/369200?login=true	0.5 mg 1 times / day multiple, oral dose: 0.5 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status:
17552 ng × h/mL EXPERIMENT https://academic.oup.com/ecco-jcc/article/8/Supplement_1/S226/369200?login=true	1.5 mg 1 times / day multiple, oral dose: 1.5 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
28883 ng × h/mL EXPERIMENT https://academic.oup.com/ecco-jcc/article/8/Supplement_1/S226/369200?login=true	2 mg 1 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
90 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29786964/	0.6 mg 1 times / day multiple, oral dose: 0.6 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
90 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29786964/	1.2 mg single, oral dose: 1.2 mg route of administration: Oral experiment type: SINGLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
75.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32237115/	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
209 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32237115/	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered: KETOCONAZOLE	KETOCONAZOLE	LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
71.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32237115/	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered:		LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
11.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32237115/	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered: RIFAMPIN	RIFAMPIN	LAQUINIMOD plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29786964/			LAQUINIMOD plasma	Homo sapiens

Doses

Dose	Population	Adverse events
2.7 mg 1 times / day multiple, oral Highest studied dose Dose: 2.7 mg, 1 times / day Route: oral Route: multiple Dose: 2.7 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28859672/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28859672/	Disc. AE: Vomiting, Nausea... AEs leading to discontinuation/dose reduction: Vomiting (8.3%) Nausea (8.3%) Tension headache (8.3%) CRP increased (8.3%) Blood fibrinogen increased (8.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/28859672/
0.6 mg 1 times / day multiple, oral Studied dose Dose: 0.6 mg, 1 times / day Route: oral Route: multiple Dose: 0.6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28243182/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28243182/	Disc. AE: Abdominal pain upper, ALT increased... AEs leading to discontinuation/dose reduction: Abdominal pain upper (0.8%) ALT increased (0.7%) Abdominal pain (0.7%) Transaminases increased (0.5%) Headache (0.5%) Diarrhea (0.4%) GGT increased (0.3%) Asthenia (0.2%) Nausea (0.2%) Cough (0.2%) Pyrexia (0.2%) Liver function test abnorma (0.2%) Decreased appetite (0.2%) Dizziness (0.2%) Depression (0.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/28243182/

AEs

PubMed

Title	Date	PubMed
Determination of laquinimod in plasma by coupled-column liquid chromatography with ultraviolet absorbance detection.	2003 Mar 5	12554144
Gateways to clinical trials.	2004 Jul-Aug	15349141
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	15465591
[Future possibilities of the multiple sclerosis treatment].	2005	16279429
Cytochrome P450 3A4 is the major enzyme responsible for the metabolism of laquinimod, a novel immunomodulator.	2005 Jun	15764719
Synthesis and reactivity of laquinimod, a quinoline-3-carboxamide: intramolecular transfer of the enol proton to a nitrogen atom as a plausible mechanism for ketene formation.	2006 Feb 17	16468821
Identification and development of new therapeutics for multiple sclerosis.	2008 Nov	18804288
Kynurenine pathway metabolites in humans: disease and healthy States.	2009	22084578
Recent developments in multiple sclerosis therapeutics.	2009 Dec 7	19968863
Recent advances in the treatment of amyotrophic lateral sclerosis. Emphasis on kynurenine pathway inhibitors.	2009 Mar	20021336
The future of multiple sclerosis therapy.	2009 Oct	19717009
Multiple sclerosis therapies: molecular mechanisms and future.	2010	20838962
Laquinimod suppress antigen presentation in relapsing-remitting multiple sclerosis: in-vitro high-throughput gene expression study.	2010 Apr 15	20347159
Identification of targets and new developments in the treatment of multiple sclerosis--focus on cladribine.	2010 Jul 21	20689698
New drug therapies for multiple sclerosis.	2010 Jun	20414110
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	20834039
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	20684995
Treatment options for multiple sclerosis: current and emerging therapies.	2010 Sep	20795847
Disease-modifying therapies in relapsing-remitting multiple sclerosis.	2010 Sep 7	20856600

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:21:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:46 GMT 2025`
Record UNII	4H914M0CSP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LAQUINIMOD SODIUM

Official Name

English

LAQUINIMOD SODIUM SALT

Preferred 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 [WHO-DD]

Common Name

English

TV-5600

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

466114