Laquinimod

Modify Date: 2024-01-07 09:08:08

Laquinimod Structure
Laquinimod structure
 Common Name Laquinimod
CAS Number 248281-84-7 Molecular Weight 356.80
Density 1.4±0.1 g/cm3 Boiling Point 546.0±50.0 °C at 760 mmHg
Molecular Formula C19H17ClN2O3 Melting Point N/A
MSDS N/A Flash Point 284.0±30.1 °C

 Use of Laquinimod


Laquinimod is a potent immunomodulator which prevents neurodegeneration and inflammation in the central nervous system.

 Names

Name 5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenylquinoline-3-carboxamide
Synonym More Synonyms

 Laquinimod Biological Activity

Description Laquinimod is a potent immunomodulator which prevents neurodegeneration and inflammation in the central nervous system.
Related Catalog
Target

NF-κB

In Vitro Laquinimod reverses EAE and inhibits pathogenic T cell immune responses. Laquinimod reverses RR-EAE and inhibits inflammatory T cell responses via a direct effect on myeloid APC. Laquinimod alters myeloid APC subsets and inhibits Th1 and Th17 polarization of myelin-specific T cells. Laquinimod-induced type II (M2) monocytes reverse established EAE[1]. Laquinimod modulates the phenotype of B cells of healthy donors. Laquinimod modulates expression of markers related to regulatory capacity in B cells of RRMS patients. Laquinimod reduces IFNγ cytokine expression in CD4+ T cells[2].
In Vivo Laquinimod treatment inhibits donor myelin-specific T cells from transferring EAE to naive recipient mice. In vivo laquinimod treatment alters subpopulations of myeloid antigen presenting cells (APC) that include a decrease in CD11c+CD11b+CD4+ dendritic cells (DC) and an elevation of CD11bhiGr1hi monocytes[1].
Cell Assay Purified CD11b+ cells from laquinimod- or vehicle-treated mice are cultured with naive CD4+ cells isolated from laquinimod- or vehicle-treated 2D2 mice and antigen (MOG p35-55, 20 µg/mL). Cells are cultured in 96-well microtitre plates at a concentration of 0.25×106 cells/mL. Culture medium consisted of RPMI 1640 supplemented with L-glutamine (2 mM), sodium pyruvate (1 mM), penicillin (100 U/mL), streptomycin (0.1 mg/mL), 2-mercaptoethanol (5×10-5 M) and 10% (v/v) fetal bovine serum. Cells are incubated for 48 h and pulsed for 18 h with 1 µCi per well of [3H]-thymidine before harvesting.
Animal Admin Seven to 10-week-old female C57BL/6, DBA/1 or SJL/J mice are injected subcutaneously with 50 µg MOG p35-55, 50 µg rMOG or 100 µg PLP p139-151, respectively, in complete Freund's adjuvant. After immunization and 2 days later, mice receive 200 ng (C57BL/6) or 100 ng (SJL/J) pertussis toxin intraperitoneally (i.p.). For adoptive transfer, donor SJL/J mice are immunized as described above and treated daily with laquinimod or vehicle. 10 days later, cells from draining lymph nodes and spleen are isolated, re-stimulated for 48 h (20 µg/mL PLP p139-151), and injected i.p. into naive SJL/J recipients (107 cells per mouse). Animals are observed daily and clinical scores are assessed as follows: 0, no signs; 1, decreased tail tone; 2, mild monoparesis or paraparesis; 3, severe paraparesis; 4, paraplegia and/or quadraparesis; and 5, moribund or death.
References

[1]. Schulze-Topphoff, Ulf., et al. Laquinimod, a quinoline-3-carboxamide, induces type II myeloid cells that modulate central nervous system autoimmunity. PLoS One (2012), 7(3), e33797.

[2]. Toubi E, et al. Laquinimod modulates B cells and their regulatory effects on T cells in Multiple Sclerosis. J Neuroimmunol. 2012 Oct 15;251(1-2):45-54.

[3]. Brück W, et al. Reduced astrocytic NF-κB activation by laquinimod protects from cuprizone-induced demyelination. Acta Neuropathol. 2012 Sep;124(3):411-24.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 546.0±50.0 °C at 760 mmHg
Molecular Formula C19H17ClN2O3
Molecular Weight 356.80
Flash Point 284.0±30.1 °C
PSA 87.42000
LogP 2.79
Vapour Pressure 0.0±1.5 mmHg at 25°C
Index of Refraction 1.587

 MSDS

Material Safety Data Sheet
Section1. Identification of the substance
Product Name: Laquinimod
Synonyms:
Section2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
Section3. Composition/information on ingredients.
Ingredient name:Laquinimod
CAS number:248281-84-7
Section4. First aid measures
Skin contact:Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact:Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation:Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion:Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Section5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.
Section6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution:Wear approved mask/respirator
Hand precaution:Wear suitable gloves/gauntlets
Skin protection:Wear suitable protective clothing
Eye protection:Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.
Section7. Handling and storage
Handling:This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:
Section8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.
Section9. Physical and chemical properties
Appearance:Not specified
Boiling point:No data
No data
Melting point:
Flash point:No data
Density:No data
Molecular formula:C19H17ClN2O3
Molecular weight:356.8
Section10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.
Section11. Toxicological information
No data.
Section12. Ecological information
No data.
Section13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.
Section14. Transportation information
Non-harzardous for air and ground transportation.
Section15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

SECTION 16 - ADDITIONAL INFORMATION
N/A

 Safety Information

Hazard Codes T+
HS Code 2933790090

 Synthetic Route

 Customs

HS Code 2933790090
Summary 2933790090. other lactams. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:9.0%. General tariff:20.0%

 Synonyms

5-Chloro-N-Et-4-hydroxy-1-methyl-2-oxo-N-Ph-1,2-dihydroquinoline-3-carboxamide
5-chloro-N-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinolinecarboxamide
5-CHLORO-N-ETHYL-4-HYDROXY-1-METHYL-2-OXO-N-PHENYL-1,2-DIHYDROQUINOLINE-3-CARBOXAMIDE
5-chloro-n-ethyl-2-hydroxy-1-methyl-4-oxo-n-phenyl-1,4-dihydroquinoline-3-carboxamide
5-Chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl-phenyl-amide
Lanquinimod
Laquinimod
2-{[(2,4-Dichlorophenoxy)acetyl]amino}ethyl thiocyanate
N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide
Thiocyanic acid, 2-[[2-(2,4-dichlorophenoxy)acetyl]amino]ethyl ester
5-chloro-1,2-dihydro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinoline carboxamide
5-Chloro-4-hydroxy-1-methyl-2-oxo-N-ethyl-N-phenyl-1,2-dihydroquinoline-3-carboxamide
N-ethyl-N-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide
[14C]-Laquinimod
ABR-215062
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