Zileuton

Class: Leukotriene Modifiers
VA Class: RE109
Molecular Formula: C₁₁H₁₂N₂O₂S
CAS Number: 111406-87-2
Brands: Zyflo

Introduction

Antiasthmatic agent; a leukotriene synthesis inhibitor.^{1 2}

Uses for Zileuton

Asthma

Prevention and long-term symptomatic management of asthma; used as an alternative, but not preferred adjunctive therapy.^{b 38 45}

In patients with mild persistent asthma, low-dose orally inhaled corticosteroids considered first-line agents for long-term control.^{21 24 28 29 38 39 45 47} Alternative agents, including certain leukotriene modifiers (i.e., montelukast, zafirlukast), may be used^{4 5 21 24} but are less effective²⁴ than inhaled corticosteroids and are not preferred as initial therapy.^{38 39 45 47}

In patients with moderate persistent asthma, low-dose inhaled corticosteroids with a long-acting inhaled β₂-agonist bronchodilator (e.g., salmeterol, formoterol) or monotherapy with medium-dose inhaled corticosteroids preferred for long-term control.^{24 38 39 45} However, consider use of long-acting inhaled β₂-agonists only as additional therapy in patients whose asthma is inadequately controlled with other asthma controller drugs or whose disease severity warrants treatment with 2 maintenance therapies.^{40 41 42 43 44 49 50 51}

Alternative agents, including certain leukotriene modifiers (i.e., montelukast, zafirlukast), can be added to a low dosage of inhaled corticosteroid for treatment of moderate persistent asthma, but these options are less effective.^{38 39 45} Considerations favoring combination with orally inhaled corticosteroids include intolerance to long-acting β₂-adrenergic agonists, marked preference for oral therapy, and demonstration of superior responsiveness to these leukotriene modifiers.^{38 45}

Not recommended for relief of acute bronchospasm; however, may continue therapy during acute asthma exacerbations.^{1 46} (See Acute Asthma under Cautions.)

Zileuton Dosage and Administration

Administration

Oral Administration

Administer orally in 4 equally divided doses daily without regard to meals.¹

Dosage

Pediatric Patients

Asthma

Oral

Children ≥12 years of age: 600 mg 4 times daily.¹

Adults

Asthma

Oral

600 mg 4 times daily.¹

Prescribing Limits

Pediatric Patients

Asthma

Oral

Children ≥12 years of age: Maximum 2.4 g daily.^b

Adults

Asthma

Oral

Maximum 2.4 g daily.^b

Special Populations

Hepatic Impairment

No specific dosage recommendations at this time.^a Do not use in patients with active liver disease or transaminases ≥3 times the ULN.^{1 27} (See Contraindications and also Hepatic Effects under Cautions.)

Renal Impairment

Dosage adjustment not required.^{a b}

Geriatric Patients

Dosage adjustment not required.^{a b}

Cautions for Zileuton

Contraindications

Active liver disease or serum aminotransferase concentrations ≥3 times the ULN.^{1 27} (See Hepatic Effects under Cautions.)

Known hypersensitivity to zileuton or any ingredient in the formulation.^{1 27}

Warnings/Precautions

Warnings

Acute Asthma

Do not use for the relief of acute bronchospasm (including status asthmaticus); zileuton can be continued during acute exacerbations of asthma, but it will not provide immediate symptomatic relief.¹

Interactions

Possible serious and/or life-threatening events associated with concomitant use with drugs dependent on CYP isoenzymes for metabolism (e.g., theophylline, propranolol, warfarin).^{1 23 27 30} (See Specific Drugs under Interactions.)

General Precautions

Hepatic Effects

Associated with increases in serum aminotransferase values (e.g., serum ALT);^{1 27} generally occurs within the first 3 months of therapy.^{1 27} Possible increased risk for ALT elevations in patients with pre-existing aminotransferase elevations and women ≥65 years of age.²⁷

Perform liver function tests (serum ALT) before initiating therapy, then once a month for 3 months, every 2–3 months for the remainder of the first year, and periodically thereafter.^{1 27} Discontinue therapy if signs or symptoms of liver dysfunction (e.g., right upper quadrant pain, nausea, fatigue, lethargy, pruritus, jaundice, “flu-like” symptoms) occur or serum ALT concentrations ≥5 times the ULN; monitor serum ALT concentrations until they return to normal.^{1 27}

Use contraindicated in patients with active liver disease or serum ALT concentrations ≥3 times the ULN.^{1 27} (See Contraindications under Cautions.) Use with caution in patients who consume large quantities of alcohol, those with mild hepatic impairment (serum ALT <3 times the ULN), and those with history of liver disease.^{1 27}

Neuropsychiatric Effects

Neuropsychiatric events reported with zileuton during postmarketing experience.^{48 52 53} Data from placebo-controlled trials with leukotriene modifiers indicate that suicidal ideation occurred in 0.01% of 9929 patients treated with montelukast and in none of those receiving other leukotriene modifiers; no completed suicide occurred during therapy with any leukotriene modifier.⁵² FDA concluded that some neuropsychiatric events reported with zileuton (e.g., sleep disorders, behavior changes) appear consistent with a drug-induced effect.^{1 46 53}

Be alert to the potential for neuropsychiatric events in patients receiving the drug.^{1 46 53} Instruct patients to contact their clinician if behavior or mood changes occur.^{1 46 53} Carefully evaluate the risks and benefits of continuing zileuton therapy in patients who develop neuropsychiatric symptoms.^{1 46 53}

Specific Populations

Pregnancy

Category C.^b

Lactation

Distributed into milk in rats; not known whether distributed into human milk.^b Discontinue nursing or the drug.^b

Pediatric Use

Safety and efficacy not established in children <12 years of age.^b

Geriatric Use

Pharmacokinetics similar to those in younger adults.¹ Possible increased risk for ALT elevations in women ≥65 years of age.²⁷

Hepatic Impairment

Contraindicated in patients with active liver disease or serum ALT concentrations ≥3 times the ULN.²⁷ (See Contraindications under Cautions.) Use with caution in patients with mild hepatic impairment (serum ALT <3 times the ULN) and/or those with history of liver disease.^{1 27} (See Hepatic Effects under Cautions.)

Renal Impairment

Pharmacokinetics not altered.¹

Common Adverse Effects

Dyspepsia, nausea, abdominal pain, pain (unspecified), headache.^b

Interactions for Zileuton

Metabolized principally by CYP1A2, CYP2C9, and CYP3A4;^b may inhibit CYP1A and CYP3A.^{1 27 30}

Specific Drugs

Drug	Interaction	Comments
Antihistamines (terfenadine and astemizole [no longer commercially available in the US])	Increased plasma terfenadine concentrations; no substantial changes in QTc interval 34 35 Possible increased plasma astemizole concentrations34 35	Concomitant use not recommended1 34 35 36 37
Calcium channel blockers, dihydropyridine	Possible increased plasma concentrations of dihydropyridine calcium-channel blocking agentsb	Concomitant use not evaluated; appropriate monitoring recommended with concomitant useb
Cisapride (no longer commercially available in the US)	Possible increased plasma cisapride concentrationsb	Concomitant use not evaluated; appropriate monitoring recommended with concomitant useb
Contraceptives, oral (ethinyl estradiol)	Pharmacokinetic interactions unlikelyb
Cyclosporine	Possible increased plasma cyclosporine concentrationsb	Concomitant use not evaluated; appropriate monitoring recommended with concomitant useb
Digoxin	Pharmacokinetic interactions unlikelyb
Naproxen	Pharmacokinetic interactions unlikelyb
Phenytoin	Pharmacokinetic interactions unlikelyb
Prednisone	Pharmacokinetic interactions unlikelyb
Propranolol	Significant increase in plasma propranolol concentrations resulting in increased β-adrenergic blockade 1	Close monitoring recommended; reduce propranolol dosage as necessary1
Sulfasalazine	Pharmacokinetic interactions unlikelyb
Theophylline	Significant increase in plasma theophylline concentrations1 27 30	Reduce theophylline dosage by approximately 50% and monitor plasma theophylline concentrations;1 adjust dosage and/or dosing interval if indicated1 30
Warfarin	Possible increased plasma warfarin concentrations and clinically significant increases in PT1 23	Closely monitor PT; adjust anticoagulant dosage if indicated1 23

Zileuton Pharmacokinetics

Absorption

Bioavailability

Rapidly absorbed following oral administration; however absolute bioavailability is not known.^b

Onset

Following oral administration, improvement in asthma symptoms and/or lung function evident within 2–5 hours.^{1 5 6 8 14 17 19}

Food

Food increases peak plasma concentration but does not affect extent of absorption.^b

Distribution

Extent

Distributed into milk in rats; not known whether distributed into human milk.^b

Plasma Protein Binding

93% (mainly albumin).^b

Elimination

Metabolism

Oxidatively metabolized to inactive metabolites principally via CYP1A2, CYP2C9, and CYP3A4.^b

Elimination Route

Excreted in urine (94.5%) and in feces (2.2%) as metabolites and unchanged drug.^b

Half-life

Terminal half-life averages 2.5 hours.^b

Stability

Storage

Oral

Tablets

20–25°C; protect from light.^b

ActionsActions

• 
  

  Inhibits 5-lipoxygenase, the first dedicated enzyme active in the conversion of arachidonic acid to leukotrienes;^{3 4 12 19} results in inhibition of leukotriene B₄ (LTB₄), and the cysteinyl leukotrienes C₄ (LTC₄), D₄ (LTD₄), and E₄ (LTE₄).^{1 13 15 18 19 22}

  
  


• 
  

  May reduce airway symptoms, decrease bronchial smooth muscle tone, and improve asthma control.^{3 4 6 8 14 17} May also reduce markers of airway inflammation (e.g., eosinophils, mast cells, activated lymphocytes, macrophages, cytokines) in airway tissue or airway secretions and reduce the intensity of airway hyperresponsiveness.^{21 31 32 33}

  
  


• 
  

  Does not inhibit either the acute bronchoconstrictor response (immediate/early asthmatic response [IAR, EAR]) or the delayed inflammatory response (late asthmatic response [LAR]) to inhaled antigen and irritants.^{3 4 7 10 11 12 13 15 18 22}

  
  


• 
  

  Does not appear to produce appreciable bronchodilation in healthy individuals.¹⁴

  
  

Advice to Patients

• 
  

  Importance of taking zileuton at regular intervals, when asymptomatic as well as during periods of worsening asthma.^b

  
  


• 
  

  Importance of contacting clinician if asthma is not well controlled; seek medical attention if short-acting, inhaled β₂-adrenergic bronchodilators are needed more often than usual or if more than the maximum number of inhalations for a 24-hour period are needed.¹

  
  


• 
  

  Importance of not using zileuton for the relief of bronchospasm.^b Patients should be provided with and instructed in the use of a short-acting, inhaled β₂-adrenergic bronchodilator as supplemental therapy for acute asthma symptoms.^b

  
  


• 
  

  Importance of not discontinuing or reducing the dosage of other antiasthmatic agents unless instructed to do so by the clinician.^b

  
  


• 
  

  Risk of liver toxicity; importance of immediately informing clinician if right upper quadrant pain, nausea, fatigue, lethargy, pruritus, jaundice, or “flu-like” symptoms occur.^b

  
  


• 
  

  Importance of informing clinicians if behavior or mood changes occur.^{1 46 53}

  
  


• 
  

  Importance of women informing their clinician if they are or plan to become pregnant or plan to breast-feed.^b

  
  


• 
  

  Importance of informing clinicians of existing or contemplated concomitant therapy, including prescription and OTC drugs, and alcohol consumption.^b

  
  


• 
  

  Importance of informing patients of other important precautionary information.^b (See Cautions.)

  
  

Preparations

Excipients in commercially available drug preparations may have clinically important effects in some individuals; consult specific product labeling for details.

Zileuton

Routes	Dosage Forms	Strengths	Brand Names	Manufacturer
Oral	Tablets, film-coated	600 mg	Zyflo (scored)	Cornerstone Therapeutics
	Tablets, film-coated, extended-release	600 mg	Zyflo CR	Cornerstone Therapeutics

Comparative Pricing

This pricing information is subject to change at the sole discretion of DS Pharmacy. This pricing information was updated 03/2011. Actual costs to patients will vary depending on the use of specific retail or mail-order locations and health insurance copays.

Zyflo CR 600MG 12-hr Tablets (CORNERSTONE BIOPHARMA): 120/$609.98 or 360/$1797.98

Disclaimer

This report on medications is for your information only, and is not considered individual patient advice. Because of the changing nature of drug information, please consult your physician or pharmacist about specific clinical use.

The American Society of Health-System Pharmacists, Inc. and Drugs.com represent that the information provided hereunder was formulated with a reasonable standard of care, and in conformity with professional standards in the field. The American Society of Health-System Pharmacists, Inc. and Drugs.com make no representations or warranties, express or implied, including, but not limited to, any implied warranty of merchantability and/or fitness for a particular purpose, with respect to such information and specifically disclaims all such warranties. Users are advised that decisions regarding drug therapy are complex medical decisions requiring the independent, informed decision of an appropriate health care professional, and the information is provided for informational purposes only. The entire monograph for a drug should be reviewed for a thorough understanding of the drug's actions, uses and side effects. The American Society of Health-System Pharmacists, Inc. and Drugs.com do not endorse or recommend the use of any drug. The information is not a substitute for medical care.

AHFS Drug Information. © Copyright, 1959-2011, Selected Revisions June 2010. American Society of Health-System Pharmacists, Inc., 7272 Wisconsin Avenue, Bethesda, Maryland 20814.

References

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23. Awni WM, Hussein Z, Granneman GR et al. Pharmacodynamic and stereoselective pharmacokinetic interactions between zileuton and warfarin in humans. Clin Pharmacokinet. 1995; 29(Suppl 2):67-76. [PubMed 8620673]

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25. Awni WM, Cavanaugh JH, Braeckman RA et al. The effect of mild or moderate hepatic impairment (cirrhosis) on the pharmacokinetics of zileuton. Clin Pharmacokinet. 1995; 29(Suppl 2):49-61. [PubMed 8620671]

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34. Hoechst Marion Roussel. Seldane (terfenadine) tables prescribing information. Kansas City, MO; 1997 Sep.

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