Pranlukast Chemical Properties

Melting point:

236-238°C

Density 

1.374±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Soluble in DMSO (up to 25 mg/ml)

pka

4.96±0.10(Predicted)

form 

solid

color 

White

Merck 

14,7710

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.

CAS DataBase Reference

103177-37-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

F,C

Risk Statements 

11-34

Safety Statements 

16-26-36/37/39-45

RTECS 

CV5647500

HS Code 

2934.99.4400

Toxicity

LD50 in male mice (mg/kg): >1000 i.v. (Toda)

Pranlukast Usage And Synthesis

Asthma drugs

Pranlukast is a common respiratory drug, it belongs to asthma drugs , it is the cysteinyl leukotrienes (LTs) receptor antagonist and it can bind to LTC4, LTD4, LTE4 receptors selectively to antagonize their effect . Roles and application are similar to zafirlukast. It is clinically used for the prevention of bronchial asthma. Oral 225mg once, 2 times one day, morning and evening after meal. After taking ,there may be gastrointestinal reactions,or there may be nausea, vomiting, abdominal pain, diarrhea or constipation, sometimes , fever, rash, pruritus and liver function abnormalities such as serum aminotransferase or bilirubin increase are visible . Pregnant women should use with caution , the elderly should take appropriate reductions. This product can not alleviate the onset of asthma.
At present, three leukotriene receptor antagonists are used for the following purposes:
1, zafirlukast :it is effective for mild to moderate asthma ,it can cause improvement in dose-dependent lung function, and reduce the amount of β agonists. Absorption of the product is affected by food, it should not be taken together with food. Oral each 20mg, 2 times/d.
2, montelukast: it is valid for intermittent or persistent asthma in adults and children. This product is approved by the FDA for the treatment of children aged 6 to 12. Absorption of the product is not affected by food, it can be taken with food . Oral each 10mg, once/d.
3, pranlukast :it is used for mild to moderate asthma, pranlukast can increase patients maximum expiratory flow,and improve asthma symptoms, it can be used as a daily treatment of chronic asthma. Each oral 450mg, 2 times/d.
The above information is edited by the chemicalbook of Tian Ye.

Description

Pranlukast, a novel chromone derivative, was introduced in Japan for the treatment of bronchial asthma and allergic diseases. Pranlukast is a highly potent, selective and competitive antagonist of peptidoleukotrienes with high affinity for the LTD₄ receptor. In patients with bronchial asthma, pranlukast was reported to induce significant improvement in both immediate and late asthmatic response induced by antigen. Pranlukast is also being evaluated clinically for the treatment of perennial allergic rhinitis, pediatric asthma, and cutaneous pruritus in dialysis patients. The therapeutic potential of pranlukast in managing irritable bowel syndrome has been suggested.

Chemical Properties

Off-white solid

Originator

Ono (Japan)

Uses

A potent, selective and orally active CysLT receptor antagonist. Leukotriene antagonist. Used as an antiasthmatic

Uses

antiasthmatic;leukotriene receptor-1 antagonist

Uses

Labeled Pranlukast, intended for use as an internal standard for the quantification of Pranlukast by GC- or LC-mass spectrometry.

Definition

ChEBI: N-[4-oxo-2-(2H-tetrazol-5-yl)-1-benzopyran-8-yl]-4-(4-phenylbutoxy)benzamide is a member of chromones.

brand name

Onon

Biological Activity

Selective cysteinyl leukotriene receptor 1 (CysLT 1 ) antagonist (IC 50 values are ~ 4-7 and 3620 nM for CysLT 1 and CysLT 2 respectively). Inhibits contraction of airway smooth muscle, microvascular leakage into airways and eosinophil infiltration. Can decrease symptoms of bronchial asthma.

References

1) Nakai?et al. (1988),?New Potent Antagonists of Leukotrienes C4 and D4. 1. Synthesis and Structure-Activity Relationships; J. Med. Chem.?31?84 2) Taniguchi?et al.?(1993),?The effect of an oral leukotriene antagonist, ONO-1078, on allergen-induced immediate bronchoconstriction in asthmatic subjects; J. Allergy Clin. Immunol.?92?507 3) Ciana?et al.?(2006),?The orphan receptor GPR17 identified as a new dual uracil nucleotides/cysteinyl-leukotrienes receptor; EMBO J.?25?4615 4) Hennen?et al. (2013),?Decoding Signaling and Function of the Orphan G Protein-Coupled Receptor GPR17 with a Small-Molecule Agonist; Sci. Signal.?6?ra93

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