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
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)
DescriptionCurator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020547s027lbl.pdf
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020547s027lbl.pdf
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 1.1 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | ACCOLATE Approved UseACCOLATE is indicated for the prophylaxis and chronic treatment of asthma in adults and children 5 years of age and older. Launch Date1996 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
352.7 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11888331 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZAFIRLUKAST plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1090.41 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11888331 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZAFIRLUKAST plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.3 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11888331 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZAFIRLUKAST plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
Other AEs: Pharyngitis, Headache... Other AEs: Pharyngitis (24.7%) Sources: Headache (13.8%) Myalgia (3.7%) Sinusitis (3.5%) Flu syndrome (3.3%) Cough increased (3.1%) Rash (3.1%) Rhinitis (3.1%) Accidental injury (3.1%) Nausea (3.1%) Back pain (2.9%) Hypertonia (2.9%) Diarrhea (2.7%) Exacerbation of asthma (2.7%) |
20 mg 2 times / day multiple, oral Highest studied dose Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 37 n = 67 Health Status: unhealthy Condition: asthma, moderate Age Group: 37 Sex: M+F Population Size: 67 Sources: |
Other AEs: Headache, Gastritis... Other AEs: Headache (7%) Sources: Gastritis (1%) Pharyngitis (20%) Rhinitis (7%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Headache | 13.8% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Diarrhea | 2.7% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Exacerbation of asthma | 2.7% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Back pain | 2.9% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Hypertonia | 2.9% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Pharyngitis | 24.7% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Accidental injury | 3.1% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Cough increased | 3.1% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Nausea | 3.1% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Rash | 3.1% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Rhinitis | 3.1% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Flu syndrome | 3.3% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Sinusitis | 3.5% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Myalgia | 3.7% | 20 mg 2 times / day multiple, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 12-76 n = 514 Health Status: unhealthy Condition: asthma, mild-to-moderate Age Group: 12-76 Sex: M+F Population Size: 514 Sources: |
| Gastritis | 1% | 20 mg 2 times / day multiple, oral Highest studied dose Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 37 n = 67 Health Status: unhealthy Condition: asthma, moderate Age Group: 37 Sex: M+F Population Size: 67 Sources: |
| Pharyngitis | 20% | 20 mg 2 times / day multiple, oral Highest studied dose Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 37 n = 67 Health Status: unhealthy Condition: asthma, moderate Age Group: 37 Sex: M+F Population Size: 67 Sources: |
| Headache | 7% | 20 mg 2 times / day multiple, oral Highest studied dose Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 37 n = 67 Health Status: unhealthy Condition: asthma, moderate Age Group: 37 Sex: M+F Population Size: 67 Sources: |
| Rhinitis | 7% | 20 mg 2 times / day multiple, oral Highest studied dose Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: |
unhealthy, 37 n = 67 Health Status: unhealthy Condition: asthma, moderate Age Group: 37 Sex: M+F Population Size: 67 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Therapeutic effect of zafirlukast as monotherapy in steroid-naive patients with severe persistent asthma. | 1999 Feb |
|
| Churg-Strauss syndrome after zafirlukast in two patients not receiving systemic steroid treatment. | 1999 Feb 27 |
|
| Zafirlukast in clinical practice: results of the Accolate Clinical Experience and Pharmacoepidemiology Trial (ACCEPT) in patients with asthma. | 1999 Jun |
|
| Characterization of the human cysteinyl leukotriene CysLT1 receptor. | 1999 Jun 24 |
|
| The leukotriene D4-receptor antagonist zafirlukast attenuates exercise-induced bronchoconstriction in children. | 1999 Mar |
|
| Zafirlukast improves asthma control in patients receiving high-dose inhaled corticosteroids. | 2000 Aug |
|
| Effects of adding a leukotriene antagonist or a long-acting beta(2)-agonist in asthmatic patients with the glycine-16 beta(2)-adrenoceptor genotype. | 2000 Aug 1 |
|
| Severe liver injury after treatment with the leukotriene receptor antagonist zafirlukast. | 2000 Dec 19 |
|
| A novel hepatointestinal leukotriene B4 receptor. Cloning and functional characterization. | 2000 Dec 29 |
|
| Acute effects of antileukotrienes on sinonasal polyposis and sinusitis. | 2000 Jan |
|
| Effectiveness and tolerability of zafirlukast for the treatment of asthma in children. | 2000 Jun |
|
| Recurrent panniculitis in a man with asthma receiving treatment with leukotriene-modifying agents. | 2000 Jun |
|
| A kinetic binding study to evaluate the pharmacological profile of a specific leukotriene C(4) binding site not coupled to contraction in human lung parenchyma. | 2000 Jun |
|
| Effect of leukotriene receptor antagonist therapy on the risk of asthma exacerbations in patients with mild to moderate asthma: an integrated analysis of zafirlukast trials. | 2000 Jun |
|
| Comparative effects of long-acting beta2-agonists, leukotriene receptor antagonists, and a 5-lipoxygenase inhibitor on exercise-induced asthma. | 2000 Sep |
|
| Characterization of the human cysteinyl leukotriene 2 receptor. | 2000 Sep 29 |
|
| A comparison of short-term treatment with inhaled fluticasone propionate and zafirlukast for patients with persistent asthma. | 2001 Aug 15 |
|
| Asthma outcome changes associated with use of the leukotriene-receptor antagonist zafirlukast. | 2001 Feb |
|
| One-year claims analysis comparing inhaled fluticasone propionate with zafirlukast for the treatment of asthma. | 2001 Jan |
|
| Fluticasone propionate compared with zafirlukast in controlling persistent asthma: a randomized double-blind, placebo-controlled trial. | 2001 Jul |
|
| Efficacy of antileukotriene agents in asthma management. | 2001 Jun |
|
| Role of cysteinyl leukotrienes in nociceptive and inflammatory conditions in experimental animals. | 2001 Jun 29 |
|
| Synergistic antiallergic activity of combined histamine H1- and cysteinyl leukotriene1-receptor blockade in human bronchus. | 2001 May 11 |
|
| The effect of low-dose inhaled fluticasone propionate on exhaled nitric oxide in asthmatic patients and comparison with oral zafirlukast. | 2001 Oct |
|
| Asthma treatment with inhaled corticosteroids versus antileukotrienes: what exhaled nitric oxide studies do and do not tell us. | 2001 Oct |
|
| Acute hepatocellular injury associated with zafirlukast. | 2001 Oct |
|
| Zafirlukast-related hepatitis: report of a further case. | 2001 Oct |
|
| Leukotriene receptor antagonists in the treatment of allergic rhinitis. | 2001 Oct |
|
| Chronic asthma. | 2001 Oct 27 |
|
| Fulminant eosinophilic endomyocarditis in an asthmatic patient treated with pranlukast after corticosteroid withdrawal. | 2001 Sep |
|
| Leukotriene receptor antagonists in the treatment of asthma: an update. | 2002 |
|
| Pharmacokinetic profile of zafirlukast. | 2002 |
|
| [Zafirlukast (Accolate): a review of its pharmacological and clinical profile]. | 2002 Apr |
|
| Pharmacological differences among CysLT(1) receptor antagonists with respect to LTC(4) and LTD(4) in human lung parenchyma. | 2002 Apr 15 |
|
| Vasculitis induced by zafirlukast therapy. | 2002 Aug |
|
| Chemoprevention by lipoxygenase and leukotriene pathway inhibitors of vinyl carbamate-induced lung tumors in mice. | 2002 Aug 1 |
|
| Participation of chemical mediators other than histamine in nasal allergy signs: a study using mice lacking histamine H(1) receptors. | 2002 Aug 9 |
|
| Pharmacoeconomic studies of asthma controller drugs: marketing gimmick or icing on the cake? | 2002 Feb |
|
| [Churg-Strauss syndrome after treatment with Singulair (montelukast)]. | 2002 Feb 20 |
|
| [Study on relationship between leukotrienes and exercise-induced asthma]. | 2002 Jan 10 |
|
| Effects of adding either a leukotriene receptor antagonist or low-dose theophylline to a low or medium dose of inhaled corticosteroid in patients with persistent asthma. | 2002 Jul |
|
| Inhaled fluticasone and zafirlukast in persistent asthma. | 2002 Mar |
|
| Comparison of second controller medications in addition to inhaled corticosteroid in patients with moderate asthma. | 2002 May |
Sample Use Guides
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
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| Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175777
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NDF-RT |
N0000000083
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NCI_THESAURUS |
C29712
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LIVERTOX |
NBK547915
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WHO-ATC |
R03DC01
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WHO-VATC |
QR03DC01
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100000091929
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107753-78-6
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GG-93
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m11576
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7244
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XZ629S5L50
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SUB00128MIG
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CHEMBL603
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C47785
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DB00549
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DTXSID5023746
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Zafirlukast
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ZAFIRLUKAST
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C062735
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114970
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XZ629S5L50
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10100
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N0000185504
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PRIMARY | Cytochrome P450 2C9 Inhibitors [MoA] |
ACTIVE MOIETY
