Montelukast sodium

Names

[ Name ]:
Montelukast sodium

[Synonym ]:
Cyclopropaneacetic acid, 1-[[[(1R)-1-[3-[(E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]-, sodium salt (1:1)
Montelukast SodiuM Hydrate
Montelukast sodium
{1-[({(1R)-1-{3-[(E)-2-(7-chloroquinoléin-2-yl)éthényl]phényl}-3-[2-(1-hydroxy-1-méthyléthyl)phényl]propyl}sulfanyl)méthyl]cyclopropyl}acétate de sodium
cyclopropaneacetic acid, 1-[[[(1R)-1-[3-[(E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]-, monosodium salt
Sodium {1-[({(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)vinyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl}sulfanyl)methyl]cyclopropyl}acetate
Natrium-{1-[({(1R)-1-{3-[(E)-2-(7-chlorchinolin-2-yl)ethenyl]phenyl}-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl}sulfanyl)methyl]cyclopropyl}acetat
[R-(E)]-1-[[[1-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic Acid Monosodium Salt
sodium {1-[({(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl}sulfanyl)methyl]cyclopropyl}acetate
sodium,2-[1-[[(1R)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanylmethyl]cyclopropyl]acetate
Montelukast sodium salt
Sodium {1-[({(1R)-1-{3-[(E)-2-(7-chloro-2-quinolinyl)vinyl]phenyl}-3-[2-(2-hydroxy-2-propanyl)phenyl]propyl}sulfanyl)methyl]cyclopropyl}acetate
Sodium 1-((((R)-m-((E)-2-(7-Chloro-2-quinolyl)vinyl)-a-(o-(1-hydroxy-1-methylethyl)phenethyl)benzyl)thio)methyl)cyclopropaneacetate
Montelukast monosodium salt
sodium {1-[({(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl}sulfanyl)methyl]cyclopropyl}acetate
Singulair
Montelukast (sodium)

Biological Activity

[Description]:

Montelukast sodium is a potent, selective CysLT1 receptor antagonist.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> GPCR/G Protein >> Leukotriene Receptor

Research Areas >> Inflammation/Immunology

[Target]

CysLT1

Autophagy

[In Vitro]

Montelukast may contribute to the reduction of eosinophilic inflammation in upper-airway inflammatory diseases such as rhinitis and nasal polyposis. Montelukast has a significant inhibitory effect on FBS-induced GM-CSF, IL-6, and IL-8 secretion, but not sICAM-1, in nasal mucosa and polyp epithelial cells. Montelukast also shows an inhibitory effect (p<0.05) on ECM-induced eosinophil survival from both nasal mucosa and polyp epithelial cells[1].

[In Vivo]

Montelukast significantly reduces mild, moderate, and part of severe exacerbations in chronic mild to moderate asthma, but it has inferior efficacy to ICS or ICS plus LABA[2]. Rats with induced asthma have up-regulated NK1R expression in the airway, and montelukast can down regulate NK1R expression during airway remodeling[3]. Blockade of CysLT1R by repeated treatment with montelukast (1 or 2 mg/kg, ig, 4 weeks) reduces Aβ1-42-induced CysLT1R expression and also suppresses Aβ1-42-induced increments of NF-κB p65, TNF-α, IL-1β and caspase-3 activation, and Bcl-2 downregulation in the hippocampus and cortex. Correspondingly, montelukast treatment significantly improves Aβ1-42-induced memory impairment in mice, but has little effect on normal mice[4].

[Cell Assay]

Nasal mucosa and polyp epithelial cells are stimulated with fetal bovine serum (FBS) with or without MK for 24 hours, and cytokine concentrations in epithelial secretions are measured by ELISA. After incubating peripheral blood eosinophils with epithelial cell-conditioned media (ECM) with or without montelukast up to 3 days, eosinophil survival is assessed by Trypan blue dye exclusion[1].

[Animal admin]

Rats: Twenty four Sprague Dawley rats are randomLy divided into control group, asthma, and montelukast group. A rat model of asthma is induced by ovalbumin (OVA) inhalation. Normal saline is used instead of sensitizing solution and 1% OVA in the control group. Each rat in the montelukast group is given montelukast (15mg/kg) by gavage 2h before OVA inhalation. All rats are treated for 8 weeks[3]. Mice: Montelukast is dissolved in 0.5% sodium carboxymethyl cellulose (CMC-Na). Mice are randomLy assigned to 4 groups: (1) vehicle plus vehicle,(2) Aβ1-42 plus vehicle, (3) Aβ1-42 plus montelukast (1.0 mg/kg), (4) Aβ1-42 plus montelukast (2.0 mg/kg). The solutions are injected bilaterally into the cerebroventricles through the micropipette[4].

[References]

[1]. Mullol J, et al. Montelukast?reduces eosinophilic inflammation by inhibiting both epithelial cell cytokine secretion (GM-CSF, IL-6, IL-8) and eosinophil survival. J Biol Regul Homeost Agents.?2010 Oct-Dec;24(4):403-11.

[2]. Zhang HP, et al. Montelukast for prevention and treatment of asthma exacerbations in adults: Systematic review and meta-analysis. Allergy Asthma Proc. 2014 Jul-Aug;35(4):278-87.

[3]. Wei B, et al. Effect of montelukast on the expression of neurokinin-1 receptor in young asthmatic rats with airway remodeling. Zhongguo Dang Dai Er Ke Za Zhi. 2013 Apr;15(4):298-301.

[4]. Lai J, et al. Montelukast targeting the cysteinyl leukotriene receptor 1 ameliorates Aβ1-42-induced memory impairment and neuroinflammatory and apoptotic responses in mice. Neuropharmacology. 2014 Apr;79:707-14.

[Related Small Molecules]

MK-571 | Zafirlukast | Pranlukast | Nedocromil | AS-35 | LY223982 | Darbufelone mesilate | LM-1484 | Quinotolast sodium | RG-12525 | RS-601 | Tipelukast | CI-949 | CP 105696 | CP-96486

Chemical & Physical Properties

[ Boiling Point ]:
750.5ºC at 760mmHg

[ Melting Point ]:
115 °C(dec.)

[ Molecular Formula ]:
C₃₅H₃₅ClNNaO₃S

[ Molecular Weight ]:
608.165

[ Flash Point ]:
407.7ºC

[ Exact Mass ]:
607.192383

[ PSA ]:
98.55000

[ LogP ]:
7.61330

[ Appearance of Characters ]:
white to tan

[ Storage condition ]:
-20°C Freezer, Under Inert Atmosphere

[ Water Solubility ]:
DMSO: ≥8mg/mL at 60°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS05, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H318-H361fd

[ Precautionary Statements ]:
P280-P305 + P351 + P338 + P310

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
63-41-62

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
GZ0698000

[ HS Code ]:
2933499090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933499090

[ Summary ]:
2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

An evaluation of prophylactic treatments to prevent post traumatic joint stiffness.

J. Orthop. Res. 32(11) , 1520-4, (2014)

Arthrofibrosis is a major obstacle to restoring joint function after trauma. The objective of this study was to evaluate montelukast, forskolin, and triamcinolone as possible means of prophylaxis agai...

Biodegradable injectable in situ implants and microparticles for sustained release of montelukast: in vitro release, pharmacokinetics, and stability.

AAPS PharmSciTech 15(3) , 772-80, (2014)

The objective of this study was to investigate the sustained release of a hydrophilic drug, montelukast (MK), from two biodegradable polymeric drug delivery systems, in situ implant (ISI) and in situ ...

Osmotically controlled pulsatile release capsule of montelukast sodium for chronotherapy: statistical optimization, in vitro and in vivo evaluation.

Drug Deliv. 21(7) , 509-18, (2014)

The purpose of present study was to design, optimize and evaluate osmotically controlled pulsatile release capsule (PRC) of montelukast sodium (MKS) for the prevention of episodic attack of asthma in ...