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Details

Stereochemistry ACHIRAL
Molecular Formula C31H33N3O6S
Molecular Weight 575.675
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZAFIRLUKAST

SMILES

COC1=C(CC2=CN(C)C3=C2C=C(NC(=O)OC4CCCC4)C=C3)C=CC(=C1)C(=O)NS(=O)(=O)C5=C(C)C=CC=C5

InChI

InChIKey=YEEZWCHGZNKEEK-UHFFFAOYSA-N
InChI=1S/C31H33N3O6S/c1-20-8-4-7-11-29(20)41(37,38)33-30(35)22-13-12-21(28(17-22)39-3)16-23-19-34(2)27-15-14-24(18-26(23)27)32-31(36)40-25-9-5-6-10-25/h4,7-8,11-15,17-19,25H,5-6,9-10,16H2,1-3H3,(H,32,36)(H,33,35)

HIDE SMILES / InChI

Molecular Formula C31H33N3O6S
Molecular Weight 575.675
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Zafirlukast is an oral leukotriene receptor antagonist (LTRA) for the maintenance treatment of asthma, often used in conjunction with an inhaled steroid and/or long-acting bronchodilator. It is available as a tablet and is usually dosed twice daily. Zafirlukast is indicated for the prophylaxis and chronic treatment of asthma. Patients with asthma were found in one study to be 25-100 times more sensitive to the bronchoconstricting activity of inhaled LTD4 than nonasthmatic subjects. In vitro studies demonstrated that zafirlukast antagonized the contractile activity of three leukotrienes (LTC4, LTD4 and LTE4) in conducting airway smooth muscle from laboratory animals and humans. Zafirlukast prevented intradermal LTD4-induced increases in cutaneous vascular permeability and inhibited inhaled LTD4-induced influx of eosinophils into animal lungs. Zafirlukast is a selective and competitive receptor antagonist of leukotriene D4 and E4 (LTD4 and LTE4), components of slow-reacting substance of anaphylaxis (SRSA). Cysteinyl leukotriene production and receptor occupation have been correlated with the pathophysiology of asthma, including airway edema, smooth muscle constriction, and altered cellular activity associated with the inflammatory process, which contribute to the signs and symptoms of asthma. Zafirlukast is marketed by Astra Zeneca with the brand names Accolate, Accoleit, and Vanticon. It was the first LTRA to be marketed in the USA and is now approved in over 60 countries, including the UK, Japan, Taiwan, Italy, Spain, Canada, Brazil, China and Turkey.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.1 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ACCOLATE

Cmax

ValueDoseCo-administeredAnalytePopulation
352.7 ng/mL
20 mg single, oral
ZAFIRLUKAST plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1090.41 ng × h/mL
20 mg single, oral
ZAFIRLUKAST plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.3 h
20 mg single, oral
ZAFIRLUKAST plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
Should be taken at least 1 hour before or 2 hours after meals. Adults and Children 12 years of age and older The recommended dose of ACCOLATE in adults and children 12 years and older is 20 mg twice daily. Pediatric Patients 5 through 11 years of age The recommended dose of ACCOLATE in children 5 through 11 years of age is 10 mg twice daily.
Route of Administration: Oral
In Vitro Use Guide
Zafirlukast significantly inhibited 10 uM LTD4-evoked 35SO4 output in a concentration-dependent fashion, with maximal inhibition of 78% at 10 uM zafirlukast, and IC50 value of 0.6 uM.
Substance Class Chemical
Record UNII
XZ629S5L50
Record Status Validated (UNII)
Record Version