A drug that inhibits leukotriene formation, reduces the inflammatory process, and is used in the treatment of asthma.
[zi- (perhaps shortening and alteration of ENZYME) + LEU(KO)T(RIENE) + –ON3.]
Dictionary:
zi·leu·ton (zī-lū'tn) ![]() |
A drug that inhibits leukotriene formation, reduces the inflammatory process, and is used in the treatment of asthma.
[zi- (perhaps shortening and alteration of ENZYME) + LEU(KO)T(RIENE) + –ON3.]
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| Drug Info: Zileuton |
Brand names: Zyflo®
Chemical formula:

Zileuton extended-release tablets
What are Zileuton extended-release tablets?
What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:
fever or infection
if you frequently drink alcohol containing drinks
liver disease
an unusual or allergic reaction to zileuton, other medicines, foods, dyes, or preservatives
pregnant or trying to get pregnant
breast-feeding
How should this medicine be used?
Take this medicine by mouth with a glass of water. Follow the directions on your prescription label. Take it within one hour after morning and evening meals. Take your doses at regular intervals. Do not crush, chew, or cut the tablets. Do not take your medicine more often than directed.
Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed. While this medicine has been used in children as young as 12 years of age, precautions do apply.
What drug(s) may interact with Zileuton?
alosetron
astemizole
caffeine
cisapride
cyclosporine
pimozide
propranolol
tacrine
terfenadine
theophylline or aminophylline
warfarin
Tell your prescriber or health care professional about all other medicines you are taking, including non-prescription medicines, nutritional supplements, or herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.
What should I watch for while taking Zileuton?
It may take a few weeks to notice the full benefit of this medicine. Tell your doctor or health care professional if your asthma symptoms do not improve. Take this medicine even when you do not have any asthma symptoms. Feeling well is a sign the medicine is working to control your asthma. Do not stop taking your medicine unless your doctor tells you to.
Talk to your doctor about what to do if you have an acute asthma attack. This medicine does not treat an acute attack. Always have your inhaled rescue medicine for asthma attacks with you.
What side effects may I notice from receiving Zileuton?
Side effects that you should report to your prescriber or health care professional as soon as possible:
allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
dark urine
difficulty breathing, wheezing
fever
flu-like symptoms (chills, fatigue, fever, muscle aches)
unusual weakness or tiredness
yellowing of the skin or eyes
Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
abdominal pain
dizziness
headache
nausea
stomach upset
Where can I keep my medicine?
Keep out of the reach of children.
Store at room temperature between 20 and 25 degrees C (68 and 77 degrees F). Protect from light. Throw away any unused medicine after the expiration date.
Last updated: 7/1/2002
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
| Wikipedia: Zileuton |
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Zileuton
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| Systematic (IUPAC) name | |
| N-[1-(1-benzothien-2-yl)ethyl]-N-hydroxyurea | |
| Identifiers | |
| CAS number | |
| ATC code | none |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C11H12N2O2S |
| Mol. mass | 236.291 g/mol |
| Pharmacokinetic data | |
| Bioavailability | Not yet established |
| Protein binding | 93% |
| Metabolism | Hepatic (CYP1A2, CYP2C9 and CYP3A4-mediated) |
| Half life | 2.5 hours |
| Excretion | Renal |
| Therapeutic considerations | |
| Pregnancy cat. |
C(US) |
| Legal status | |
| Routes | Oral |
Zileuton (INN) is an asthma drug. It blocks leukotriene synthesis by inhibiting 5-lipoxygenase, an enzyme of the eicosanoid synthesis pathway. Zileuton was introduced in 1997 by Abbot Laboratories and is now marketed by Critical Therapeutics under the brand name ZYFLO. The original four-times-per-day immediate-release formulation of zileuton, known as ZYFLO IR, was, as of March 1, 2008, discontinued and replaced by ZYFLO CR.[1]
Contents |
Zileuton is indicated for the prophylaxis and chronic treatment of asthma in adults and children 12 years of age and older. Zileuton is not indicated for use in the reversal of bronchospasm in acute asthma attacks. Therapy with zileuton can be continued during acute exacerbations of asthma. The recommended dose of ZYFLO CR is two 600 mg extended-release tablets twice daily, within one hour after morning and evening meals, for a total daily dose of 2400 mg.
Related compounds include montelukast (Singulair) and zafirlukast (Accolate). These two compounds block the leukotriene receptor, while zileuton blocks the synthesis of leukotrienes.
Research on mice suggests that Zileuton used alone or in combination with imatinib may inhibit chronic myeloid leukemia (CML). Lethal Cancer Knocked Down By One-two Drug Punch ScienceDaily (June 8, 2009).
Zileuton frequently causes liver enzyme elevations and thus are contraindicated in patients with active liver disease or transaminase elevations greater than or equal to three times the upper limit of normal. Liver enzymes should be monitored prior to administering zileuton and repeated on a regular basis while patients are on the medication.
Zileuton is a weak inhibitor of CYP1A2[2] and thus has several clinically important drug interactions, such as inhibiting warfarin and theophylline metabolism. It lowered theophylline clearance significantly, doubling the AUC and prolonging half-life by nearly 25%. Because of theophylline's relation to caffeine (both being a methylxanthine, and theophylline being a metabolite of caffeine), caffeine's metabolism and clearance may also be reduced.[3] The R-isomer of warfarin metabolism and clearance is mainly affected by zileuton, while the S-isomer is not (because of metabolism via different enzymes). This can lead to an increase in prothrombin time.[4]
Zileuton is an active oral inhibitor of the enzyme 5-lipoxygenase, which forms leukotrienes from arachidonic acid. The chemical name of zileuton is (±)-1-(1-Benzo[b]thien-2-ylethyl)-l-hydroxyurea.
The molecular formula of zileuton is C11H12N2O2S with a molecular weight of 236.29. The formulation from the manufacturer is a racemic mixture of R(+) and S(-) enantiomers.[5]
Following oral administration zileuton is rapidly absorbed with a mean time to peak serum concentration of 1.7 hours and an average half-life elimination of 2.5 hours. Plasma concentrations are proportional to dose, whereas the absoulte bioavailability is unknown.
The apparent volume of distribution of zileuton is approximately 1.2 L/kg. Zileuton is 93% bound to plasma proteins, primarily to albumin, with minor binding to alpha-1-acid glycoprotein.
Elimination of zileuton is primarily through metabolites in the urine (~95%) with the feces accounting for the next largest amount (~2%). The drug is metabolized by the cytochrome P450 enzymes: CYP1A2, 2C9, and 3A4.[5]
The most common adverse event associated with zileuton is headache (25%). Other frequently occurring adverse reactions include: pain (8%), dyspepsia (8%), nausea (6%), abdominal pain (5%), leukopenia (1%), ALT (alanine transaminase) increase (2%), asthenia (4%), and myalgia (3%).[6]
Zileuton is a minor substrate of CYP1A2, 2C8/9, 3A4, and a weak inhibitor of CYP 1A2. The drug has been shown to increase the serum concentration or effects of theophylline, propranolol, and warfarin. It is advised that the doses of each medication be monitored and/or reduced accordingly.
The avoidance of alcohol is recommended due to increase risk of CNS depression as well as an increase risk in liver toxicity. In addition, the herbal supplement St. John's wort may decrease the serum levels of zileuton.[6]
Other neuropschiatric events noted postmarketing include agitation, aggression, anxiousness, dream abnormalities and hallucinations, depression, insomnia, irritability, restlessness, suicidal thinking and behavior [including suicide], and tremor,
In humans symptoms of overdose are limited. The minimum oral lethal doses in mice and rats were 500-4000 and 300-1000 mg/kg, respectively (providing greater than 3 and 9 times the systemic exposure [AUC] achieved at the maximum recommended human daily oral dose). No deaths occurred, but nephritis was reported in dogs at an oral dose of 1000 mg/kg (providing in excess of 12 times the systemic exposure [AUC] achieved at the maximum recommended human daily oral dose). In the case of a suspected overdose a certified poison control center should be consulted for updated information regarding management of overdose with zileuton.
In the case of an overdose, patients should receive supportive care with treatment given only symptomatically. If indicated, the drug can be eliminated through emesis or gastric lavage with proper measures to ensure airway patency.[6]
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| Zyflo (trademark) | |
| Cornerstone Therapeutics Inc | |
| Zileuton extended-release tablets |
Copyrights:
![]() | Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2007. Published by Houghton Mifflin Company. All rights reserved. Read more | |
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