Identification

Name
Zileuton
Accession Number
DB00744  (APRD00265)
Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Description

Leukotrienes are substances that induce numerous biological effects including augmentation of neutrophil and eosinophil migration, neutrophil and monocyte aggregation, leukocyte adhesion, increased capillary permeability, and smooth muscle contraction. These effects contribute to inflammation, edema, mucus secretion, and bronchoconstriction in the airways of asthmatic patients. Zileuton relieves such symptoms through its selective inhibition of 5-lipoxygenase, the enzyme that catalyzes the formation of leukotrienes from arachidonic acid. Specifically, it inhibits leukotriene LTB4, LTC4, LTD4, and LTE4 formation. Both the R(+) and S(-) enantiomers are pharmacologically active as 5-lipoxygenase inhibitors in in vitro systems. The immediate release tablet of Zileuton has been withdrawn from the US market.

Structure
Thumb
Synonyms
  • (+-)-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea
  • Leutrol
  • N-(1-Benzo(b)thien-2-ylethyl)-N-hydroxyurea
  • N-[1-(Benzo[b]thiophen-2-yl)ethyl]-N-hydroxyurea
  • Zileuton
  • Zileutonum
External IDs
A 64077
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ZileutonTablet, extended release600 mg/1OralAristos Phamaceuticals, Inc.2016-11-302017-05-20Us
ZileutonTablet, extended release600 mg/1OralPrasco, Llc2017-03-29Not applicableUs
ZyfloTablet600 mg/1OralChiesi Pharmaceuticals Inc.1996-12-06Not applicableUs
Zyflo CRTablet, multilayer, extended release600 mg/1OralChiesi Pharmaceuticals Inc.2007-05-30Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ZileutonTablet, extended release600 mg/1OralRising Pharmaceuticals2017-03-21Not applicableUs
International/Other Brands
Zyflo
Categories
UNII
V1L22WVE2S
CAS number
111406-87-2
Weight
Average: 236.29
Monoisotopic: 236.061948328
Chemical Formula
C11H12N2O2S
InChI Key
MWLSOWXNZPKENC-UHFFFAOYSA-N
InChI
InChI=1S/C11H12N2O2S/c1-7(13(15)11(12)14)10-6-8-4-2-3-5-9(8)16-10/h2-7,15H,1H3,(H2,12,14)
IUPAC Name
1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
SMILES
CC(N(O)C(N)=O)C1=CC2=CC=CC=C2S1

Pharmacology

Indication

For the prophylaxis and chronic treatment of asthma in adults and children 12 years of age and older.

Structured Indications
Pharmacodynamics

Zileuton is an asthma drug that differs chemically and pharmacologically from other antiasthmatic agents. It blocks leukotriene synthesis by inhibiting 5-lipoxygenase, an enzyme of the eicosanoid synthesis pathway. Current data indicates that asthma is a chronic inflammatory disorder of the airways involving the production and activity of several endogenous inflammatory mediators, including leukotrienes. Sulfido-peptide leukotrienes (LTC4, LTD4, LTE4, also known as the slow-releasing substances of anaphylaxis) and LTB4, a chemoattractant for neutrophils and eosinophils, are derived from the initial unstable product of arachidonic acid metabolism, leukotriene A4 (LTA4), and can be measured in a number of biological fluids including bronchoalveolar lavage fluid (BALF) from asthmatic patients. In humans, pretreatment with zileuton attenuated bronchoconstriction caused by cold air challenge in patients with asthma.

Mechanism of action

Leukotrienes are substances that induce numerous biological effects including augmentation of neutrophil and eosinophil migration, neutrophil and monocyte aggregation, leukocyte adhesion, increased capillary permeability, and smooth muscle contraction. These effects contribute to inflammation, edema, mucus secretion, and bronchoconstriction in the airways of asthmatic patients. Zileuton relieves such symptoms through its selective inhibition of 5-lipoxygenase, the enzyme that catalyzes the formation of leukotrienes from arachidonic acid. Specifically, it inhibits leukotriene LTB4, LTC4, LTD4, and LTE4 formation. Both the R(+) and S(-) enantiomers are pharmacologically active as 5-lipoxygenase inhibitors in in vitro systems. Due to the role of leukotrienes in the pathogenesis of asthma, modulation of leukotriene formation by interruption of 5-lipoxygenase activity may reduce airway symptoms, decrease bronchial smooth muscle tone, and improve asthma control.

TargetActionsOrganism
AArachidonate 5-lipoxygenase
inhibitor
Human
Absorption

Rapidly and almost completely absorbed. The absolute bioavailability is unknown.

Volume of distribution
  • 1.2 L/kg
Protein binding

93% bound to plasma proteins, primarily to albumin.

Metabolism

Hepatic. Zileuton and its N-dehydroxylated metabolite are oxidatively metabolized by the cytochrome P450 isoenzymes 1A2, 2C9 and 3A4.

Route of elimination

Elimination of zileuton is predominantly via metabolism with a mean terminal half-life of 2.5 hours. The urinary excretion of the inactive N-dehydroxylated metabolite and unchanged zileuton each accounted for less than 0.5% of the dose.

Half life

2.5 hours

Clearance
  • Apparent oral cl=7 mL/min/kg
Toxicity

The oral minimum lethal doses in mice and rats were 500-4000 and 300-1000 mg/kg in various preparations, respectively (providing greater than 3 and 9 times the systemic exposure [AUC] achieved at the maximum recommended human daily oral dose, respectively).

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when Zileuton is combined with 16-Bromoepiandrosterone.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when Zileuton is combined with 19-norandrostenedione.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when Zileuton is combined with 5-androstenedione.Experimental, Illicit
AbciximabZileuton may increase the anticoagulant activities of Abciximab.Approved
AbirateroneThe serum concentration of Zileuton can be increased when it is combined with Abiraterone.Approved
AcebutololZileuton may decrease the antihypertensive activities of Acebutolol.Approved
AceclofenacThe risk or severity of adverse effects can be increased when Zileuton is combined with Aceclofenac.Approved, Investigational
AcemetacinThe risk or severity of adverse effects can be increased when Zileuton is combined with Acemetacin.Approved
AcenocoumarolZileuton may increase the anticoagulant activities of Acenocoumarol.Approved
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Zileuton is combined with Acetylsalicylic acid.Approved, Vet Approved
AclarubicinZileuton may decrease the excretion rate of Aclarubicin which could result in a higher serum level.Investigational
AdapaleneThe risk or severity of adverse effects can be increased when Adapalene is combined with Zileuton.Approved
AlclofenacThe risk or severity of adverse effects can be increased when Zileuton is combined with Alclofenac.Approved, Withdrawn
AlclometasoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Alclometasone.Approved
AldosteroneThe risk or severity of adverse effects can be increased when Zileuton is combined with Aldosterone.Experimental, Investigational
Alendronic acidThe risk or severity of adverse effects can be increased when Zileuton is combined with Alendronic acid.Approved
AliskirenZileuton may decrease the antihypertensive activities of Aliskiren.Approved, Investigational
AlminoprofenThe risk or severity of adverse effects can be increased when Zileuton is combined with Alminoprofen.Experimental
AlprenololZileuton may decrease the antihypertensive activities of Alprenolol.Approved, Withdrawn
AlprostadilThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Zileuton.Approved, Investigational
AmcinonideThe risk or severity of adverse effects can be increased when Zileuton is combined with Amcinonide.Approved
AmikacinZileuton may decrease the excretion rate of Amikacin which could result in a higher serum level.Approved, Vet Approved
AmilorideZileuton may decrease the antihypertensive activities of Amiloride.Approved
AmiodaroneThe metabolism of Zileuton can be decreased when combined with Amiodarone.Approved, Investigational
AmrubicinZileuton may decrease the excretion rate of Amrubicin which could result in a higher serum level.Approved, Investigational
AncrodZileuton may increase the anticoagulant activities of Ancrod.Investigational
AndrographolideThe risk or severity of adverse effects can be increased when Zileuton is combined with Andrographolide.Investigational
AndrostenedioneThe risk or severity of adverse effects can be increased when Zileuton is combined with Androstenedione.Experimental, Illicit
AnecortaveThe risk or severity of adverse effects can be increased when Zileuton is combined with Anecortave.Investigational
anecortave acetateThe risk or severity of adverse effects can be increased when Zileuton is combined with anecortave acetate.Investigational
AnisodamineThe risk or severity of adverse effects can be increased when Zileuton is combined with Anisodamine.Investigational
annamycinZileuton may decrease the excretion rate of annamycin which could result in a higher serum level.Investigational
AntipyrineThe risk or severity of adverse effects can be increased when Zileuton is combined with Antipyrine.Approved
Antithrombin III humanZileuton may increase the anticoagulant activities of Antithrombin III human.Approved
ApixabanZileuton may increase the anticoagulant activities of Apixaban.Approved
ApocyninThe risk or severity of adverse effects can be increased when Zileuton is combined with Apocynin.Investigational
ApramycinZileuton may decrease the excretion rate of Apramycin which could result in a higher serum level.Experimental, Vet Approved
ApremilastThe risk or severity of adverse effects can be increased when Zileuton is combined with Apremilast.Approved, Investigational
AprepitantThe serum concentration of Zileuton can be increased when it is combined with Aprepitant.Approved, Investigational
ArbekacinZileuton may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved, Investigational
ArdeparinZileuton may increase the anticoagulant activities of Ardeparin.Approved, Investigational, Withdrawn
ArgatrobanZileuton may increase the anticoagulant activities of Argatroban.Approved, Investigational
ArotinololZileuton may decrease the antihypertensive activities of Arotinolol.Approved, Investigational
AtamestaneThe risk or severity of adverse effects can be increased when Zileuton is combined with Atamestane.Investigational
AtazanavirThe metabolism of Zileuton can be decreased when combined with Atazanavir.Approved, Investigational
AtenololZileuton may decrease the antihypertensive activities of Atenolol.Approved
AtomoxetineThe metabolism of Zileuton can be decreased when combined with Atomoxetine.Approved
AzapropazoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Azapropazone.Withdrawn
AzelastineThe risk or severity of adverse effects can be increased when Zileuton is combined with Azelastine.Approved
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Azilsartan medoxomil is combined with Zileuton.Approved
AzithromycinThe metabolism of Zileuton can be decreased when combined with Azithromycin.Approved
BalsalazideZileuton may increase the nephrotoxic activities of Balsalazide.Approved, Investigational
BecaplerminZileuton may increase the anticoagulant activities of Becaplermin.Approved, Investigational
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Zileuton is combined with Beclomethasone dipropionate.Approved, Investigational
BefunololZileuton may decrease the antihypertensive activities of Befunolol.Experimental
BekanamycinZileuton may decrease the excretion rate of Bekanamycin which could result in a higher serum level.Experimental
BenazeprilThe risk or severity of adverse effects can be increased when Benazepril is combined with Zileuton.Approved, Investigational
BendazacThe risk or severity of adverse effects can be increased when Zileuton is combined with Bendazac.Experimental
BendroflumethiazideThe therapeutic efficacy of Bendroflumethiazide can be decreased when used in combination with Zileuton.Approved
BenorilateThe risk or severity of adverse effects can be increased when Zileuton is combined with Benorilate.Experimental
BenoxaprofenThe risk or severity of adverse effects can be increased when Zileuton is combined with Benoxaprofen.Withdrawn
BenzydamineThe risk or severity of adverse effects can be increased when Zileuton is combined with Benzydamine.Approved
BeraprostThe therapeutic efficacy of Beraprost can be decreased when used in combination with Zileuton.Investigational
BetamethasoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Betamethasone.Approved, Vet Approved
BetaxololZileuton may decrease the antihypertensive activities of Betaxolol.Approved
BevantololZileuton may decrease the antihypertensive activities of Bevantolol.Approved
BevoniumThe risk or severity of adverse effects can be increased when Zileuton is combined with Bevonium.Experimental
BimatoprostThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Zileuton.Approved, Investigational
BisoprololZileuton may decrease the antihypertensive activities of Bisoprolol.Approved
BivalirudinZileuton may increase the anticoagulant activities of Bivalirudin.Approved, Investigational
BoceprevirThe metabolism of Zileuton can be decreased when combined with Boceprevir.Approved, Withdrawn
BopindololZileuton may decrease the antihypertensive activities of Bopindolol.Approved
BortezomibThe metabolism of Zileuton can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Zileuton can be decreased when it is combined with Bosentan.Approved, Investigational
BromfenacThe risk or severity of adverse effects can be increased when Bromfenac is combined with Zileuton.Approved
BucillamineThe risk or severity of adverse effects can be increased when Zileuton is combined with Bucillamine.Investigational
BucindololZileuton may decrease the antihypertensive activities of Bucindolol.Investigational
BudesonideThe risk or severity of adverse effects can be increased when Zileuton is combined with Budesonide.Approved
BufexamacThe risk or severity of adverse effects can be increased when Zileuton is combined with Bufexamac.Experimental
BufuralolZileuton may decrease the antihypertensive activities of Bufuralol.Experimental, Investigational
BumadizoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Bumadizone.Experimental
BumetanideZileuton may decrease the diuretic activities of Bumetanide.Approved
BupranololZileuton may decrease the antihypertensive activities of Bupranolol.Approved
CaffeineThe metabolism of Zileuton can be decreased when combined with Caffeine.Approved
CandesartanThe risk or severity of adverse effects can be increased when Candesartan is combined with Zileuton.Experimental
Candesartan cilexetilThe risk or severity of adverse effects can be increased when Candesartan cilexetil is combined with Zileuton.Approved
CandoxatrilThe risk or severity of adverse effects can be increased when Candoxatril is combined with Zileuton.Experimental
CapecitabineThe metabolism of Zileuton can be decreased when combined with Capecitabine.Approved, Investigational
CaptoprilThe risk or severity of adverse effects can be increased when Captopril is combined with Zileuton.Approved
CarbamazepineThe metabolism of Zileuton can be increased when combined with Carbamazepine.Approved, Investigational
Carbaspirin calciumThe risk or severity of adverse effects can be increased when Zileuton is combined with Carbaspirin calcium.Experimental, Investigational
Carboprost TromethamineThe therapeutic efficacy of Carboprost Tromethamine can be decreased when used in combination with Zileuton.Approved
CarprofenThe risk or severity of adverse effects can be increased when Zileuton is combined with Carprofen.Approved, Vet Approved, Withdrawn
CarteololZileuton may decrease the antihypertensive activities of Carteolol.Approved
CarvedilolZileuton may decrease the antihypertensive activities of Carvedilol.Approved, Investigational
CastanospermineThe risk or severity of adverse effects can be increased when Zileuton is combined with Castanospermine.Experimental
CelecoxibThe risk or severity of adverse effects can be increased when Celecoxib is combined with Zileuton.Approved, Investigational
CeliprololZileuton may decrease the antihypertensive activities of Celiprolol.Approved, Investigational
CeritinibThe serum concentration of Zileuton can be increased when it is combined with Ceritinib.Approved
CertoparinZileuton may increase the anticoagulant activities of Certoparin.Approved, Investigational
ChloroquineThe risk or severity of adverse effects can be increased when Chloroquine is combined with Zileuton.Approved, Vet Approved
ChlorothiazideThe therapeutic efficacy of Chlorothiazide can be decreased when used in combination with Zileuton.Approved, Vet Approved
ChlorthalidoneThe therapeutic efficacy of Chlorthalidone can be decreased when used in combination with Zileuton.Approved
CholecalciferolThe metabolism of Zileuton can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CholestyramineCholestyramine can cause a decrease in the absorption of Zileuton resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Choline magnesium trisalicylateThe risk or severity of adverse effects can be increased when Zileuton is combined with Choline magnesium trisalicylate.Approved
CiclesonideThe risk or severity of adverse effects can be increased when Zileuton is combined with Ciclesonide.Approved, Investigational
CilazaprilThe risk or severity of adverse effects can be increased when Cilazapril is combined with Zileuton.Approved
CinoxacinZileuton may increase the neuroexcitatory activities of Cinoxacin.Approved, Investigational, Withdrawn
CitalopramThe metabolism of Zileuton can be decreased when combined with Citalopram.Approved
Citric AcidZileuton may increase the anticoagulant activities of Citric Acid.Approved, Nutraceutical, Vet Approved
ClarithromycinThe metabolism of Zileuton can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Zileuton can be decreased when combined with Clemastine.Approved
ClobetasolThe risk or severity of adverse effects can be increased when Zileuton is combined with Clobetasol.Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Zileuton is combined with Clobetasol propionate.Approved
ClobetasoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Clobetasone.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Zileuton is combined with Clocortolone.Approved
Clodronic AcidThe risk or severity of adverse effects can be increased when Zileuton is combined with Clodronic Acid.Approved, Investigational, Vet Approved
ClonixinThe risk or severity of adverse effects can be increased when Zileuton is combined with Clonixin.Approved
CloprostenolThe therapeutic efficacy of Cloprostenol can be decreased when used in combination with Zileuton.Vet Approved
CloranololZileuton may decrease the antihypertensive activities of Cloranolol.Experimental
ClotrimazoleThe metabolism of Zileuton can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Zileuton can be decreased when combined with Cobicistat.Approved
ColesevelamColesevelam can cause a decrease in the absorption of Zileuton resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColestipolColestipol can cause a decrease in the absorption of Zileuton resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ConivaptanThe serum concentration of Zileuton can be increased when it is combined with Conivaptan.Approved, Investigational
Cortexolone 17α-propionateThe risk or severity of adverse effects can be increased when Zileuton is combined with Cortexolone 17α-propionate.Investigational
CorticosteroneThe risk or severity of adverse effects can be increased when Zileuton is combined with Corticosterone.Experimental
Cortisone acetateThe risk or severity of adverse effects can be increased when Zileuton is combined with Cortisone acetate.Approved
CrisaboroleThe metabolism of Zileuton can be decreased when combined with Crisaborole.Approved
CrizotinibThe metabolism of Zileuton can be decreased when combined with Crizotinib.Approved
CurcuminThe risk or severity of adverse effects can be increased when Zileuton is combined with Curcumin.Investigational
CyclopenthiazideThe therapeutic efficacy of Cyclopenthiazide can be decreased when used in combination with Zileuton.Experimental
CyclosporineZileuton may increase the nephrotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Zileuton can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
D-LimoneneThe risk or severity of adverse effects can be increased when Zileuton is combined with D-Limonene.Investigational
Dabigatran etexilateZileuton may increase the anticoagulant activities of Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Zileuton can be decreased when it is combined with Dabrafenib.Approved
DalteparinZileuton may increase the anticoagulant activities of Dalteparin.Approved
DanaparoidZileuton may increase the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarexabanZileuton may increase the anticoagulant activities of Darexaban.Investigational
DarunavirThe metabolism of Zileuton can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Zileuton can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinZileuton may decrease the excretion rate of Daunorubicin which could result in a higher serum level.Approved
DeferasiroxThe serum concentration of Zileuton can be decreased when it is combined with Deferasirox.Approved, Investigational
DeflazacortThe risk or severity of adverse effects can be increased when Zileuton is combined with Deflazacort.Approved
DelaprilThe risk or severity of adverse effects can be increased when Delapril is combined with Zileuton.Experimental
DelavirdineThe metabolism of Zileuton can be decreased when combined with Delavirdine.Approved
DesirudinZileuton may increase the anticoagulant activities of Desirudin.Approved
DesmopressinThe risk or severity of adverse effects can be increased when Zileuton is combined with Desmopressin.Approved
DesonideThe risk or severity of adverse effects can be increased when Zileuton is combined with Desonide.Approved, Investigational
DesoximetasoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Desoximetasone.Approved
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Zileuton is combined with Desoxycorticosterone acetate.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Zileuton is combined with Desoxycorticosterone Pivalate.Experimental, Vet Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Dexamethasone.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Zileuton is combined with Dexamethasone isonicotinate.Vet Approved
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Zileuton.Approved, Investigational
DextranZileuton may increase the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Zileuton may increase the anticoagulant activities of Dextran 40.Approved
Dextran 70Zileuton may increase the anticoagulant activities of Dextran 70.Approved
Dextran 75Zileuton may increase the anticoagulant activities of Dextran 75.Approved
DibekacinZileuton may decrease the excretion rate of Dibekacin which could result in a higher serum level.Experimental
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Zileuton.Approved, Vet Approved
DicoumarolZileuton may increase the anticoagulant activities of Dicoumarol.Approved
DifenpiramideThe risk or severity of adverse effects can be increased when Zileuton is combined with Difenpiramide.Experimental
DiflorasoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Diflorasone.Approved
DiflunisalThe risk or severity of adverse effects can be increased when Zileuton is combined with Diflunisal.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Zileuton is combined with Difluocortolone.Approved, Investigational
DifluprednateThe risk or severity of adverse effects can be increased when Zileuton is combined with Difluprednate.Approved
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Zileuton.Approved
DihydroergotamineThe metabolism of Zileuton can be decreased when combined with Dihydroergotamine.Approved
DihydrostreptomycinZileuton may decrease the excretion rate of Dihydrostreptomycin which could result in a higher serum level.Investigational, Vet Approved
DiltiazemThe metabolism of Zileuton can be decreased when combined with Diltiazem.Approved
DinoprostThe therapeutic efficacy of Dinoprost can be decreased when used in combination with Zileuton.Investigational
Dinoprost TromethamineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Zileuton.Approved, Vet Approved
DinoprostoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Zileuton.Approved
DosulepinThe metabolism of Zileuton can be decreased when combined with Dosulepin.Approved
DoxorubicinZileuton may decrease the excretion rate of Doxorubicin which could result in a higher serum level.Approved, Investigational
DoxycyclineThe metabolism of Zileuton can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Zileuton can be decreased when combined with Dronedarone.Approved
DrospirenoneZileuton may increase the hyperkalemic activities of Drospirenone.Approved
DroxicamThe risk or severity of adverse effects can be increased when Zileuton is combined with Droxicam.Approved
DuvelisibThe risk or severity of adverse effects can be increased when Zileuton is combined with Duvelisib.Investigational
E-6201The risk or severity of adverse effects can be increased when Zileuton is combined with E-6201.Investigational
Edetic AcidZileuton may increase the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanZileuton may increase the anticoagulant activities of Edoxaban.Approved
EfavirenzThe metabolism of Zileuton can be decreased when combined with Efavirenz.Approved, Investigational
EnalaprilThe risk or severity of adverse effects can be increased when Enalapril is combined with Zileuton.Approved, Vet Approved
EnalaprilatThe risk or severity of adverse effects can be increased when Enalaprilat is combined with Zileuton.Approved
EnoxacinZileuton may increase the neuroexcitatory activities of Enoxacin.Approved, Investigational
EnoxaparinZileuton may increase the anticoagulant activities of Enoxaparin.Approved
EnprostilThe therapeutic efficacy of Enprostil can be decreased when used in combination with Zileuton.Experimental
EnzalutamideThe serum concentration of Zileuton can be decreased when it is combined with Enzalutamide.Approved
EpanololZileuton may decrease the antihypertensive activities of Epanolol.Experimental
EpirizoleThe risk or severity of adverse effects can be increased when Zileuton is combined with Epirizole.Approved
EpirubicinZileuton may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
EplerenoneZileuton may decrease the antihypertensive activities of Eplerenone.Approved
EpoprostenolThe therapeutic efficacy of Epoprostenol can be decreased when used in combination with Zileuton.Approved
EprosartanThe risk or severity of adverse effects can be increased when Eprosartan is combined with Zileuton.Approved
EquileninThe risk or severity of adverse effects can be increased when Zileuton is combined with Equilenin.Experimental
EquilinThe risk or severity of adverse effects can be increased when Zileuton is combined with Equilin.Approved
ErythromycinThe metabolism of Zileuton can be decreased when combined with Erythromycin.Approved, Vet Approved
EsmololZileuton may decrease the antihypertensive activities of Esmolol.Approved
EstroneThe risk or severity of adverse effects can be increased when Zileuton is combined with Estrone.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Zileuton is combined with Estrone sulfate.Approved
Etacrynic acidZileuton may decrease the diuretic activities of Etacrynic acid.Approved
EtanerceptThe risk or severity of adverse effects can be increased when Etanercept is combined with Zileuton.Approved, Investigational
EthenzamideThe risk or severity of adverse effects can be increased when Zileuton is combined with Ethenzamide.Experimental
Ethyl biscoumacetateZileuton may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
Etidronic acidThe risk or severity of adverse effects can be increased when Zileuton is combined with Etidronic acid.Approved
EtodolacThe risk or severity of adverse effects can be increased when Zileuton is combined with Etodolac.Approved, Investigational, Vet Approved
EtofenamateThe risk or severity of adverse effects can be increased when Zileuton is combined with Etofenamate.Approved, Investigational
EtoricoxibThe risk or severity of adverse effects can be increased when Zileuton is combined with Etoricoxib.Approved, Investigational
EtravirineThe metabolism of Zileuton can be decreased when combined with Etravirine.Approved
Evening primrose oilThe risk or severity of adverse effects can be increased when Zileuton is combined with Evening primrose oil.Approved, Investigational
exisulindThe risk or severity of adverse effects can be increased when Zileuton is combined with exisulind.Investigational
FelbinacThe risk or severity of adverse effects can be increased when Zileuton is combined with Felbinac.Experimental
FenbufenThe risk or severity of adverse effects can be increased when Zileuton is combined with Fenbufen.Approved
FenoprofenThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Zileuton.Approved
FenprostaleneThe therapeutic efficacy of Fenprostalene can be decreased when used in combination with Zileuton.Vet Approved
FentiazacThe risk or severity of adverse effects can be increased when Zileuton is combined with Fentiazac.Experimental
FeprazoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Feprazone.Experimental
Ferulic acidZileuton may increase the anticoagulant activities of Ferulic acid.Experimental
FimasartanThe risk or severity of adverse effects can be increased when Fimasartan is combined with Zileuton.Approved, Investigational
FleroxacinZileuton may increase the neuroexcitatory activities of Fleroxacin.Approved
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Zileuton.Approved, Withdrawn
FloxuridineThe metabolism of Zileuton can be decreased when combined with Floxuridine.Approved
fluasteroneThe risk or severity of adverse effects can be increased when Zileuton is combined with fluasterone.Investigational
FluconazoleThe metabolism of Zileuton can be decreased when combined with Fluconazole.Approved
FludrocortisoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Fludrocortisone.Approved
FluindioneZileuton may increase the anticoagulant activities of Fluindione.Investigational
FlumequineZileuton may increase the neuroexcitatory activities of Flumequine.Withdrawn
FlumethasoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Flumethasone.Approved, Vet Approved
FlunisolideThe risk or severity of adverse effects can be increased when Zileuton is combined with Flunisolide.Approved, Investigational
FlunixinThe risk or severity of adverse effects can be increased when Zileuton is combined with Flunixin.Vet Approved
FlunoxaprofenThe risk or severity of adverse effects can be increased when Zileuton is combined with Flunoxaprofen.Experimental
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Zileuton is combined with Fluocinolone Acetonide.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Zileuton is combined with Fluocinonide.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Zileuton is combined with Fluocortolone.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Fluorometholone.Approved
FluorouracilThe metabolism of Zileuton can be decreased when combined with Fluorouracil.Approved
FluprednideneThe risk or severity of adverse effects can be increased when Zileuton is combined with Fluprednidene.Approved, Withdrawn
FluprednisoloneThe risk or severity of adverse effects can be increased when Zileuton is combined with Fluprednisolone.Approved
FluprostenolThe therapeutic efficacy of Fluprostenol can be decreased when used in combination with Zileuton.Vet Approved
FlurandrenolideThe risk or severity of adverse effects can be increased when Zileuton is combined with Flurandrenolide.Approved
FlurbiprofenThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Zileuton.Approved, Investigational
Fluticasone furoateThe risk or severity of adverse effects can be increased when Zileuton is combined with Fluticasone furoate.Approved
Fluticasone propionateThe risk or severity of adverse effects can be increased when Zileuton is combined with Fluticasone propionate.Approved
FluvastatinThe metabolism of Zileuton can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Zileuton can be decreased when combined with Fluvoxamine.Approved, Investigational
Folic AcidThe therapeutic efficacy of Folic Acid can be decreased when used in combination with Zileuton.Approved, Nutraceutical, Vet Approved
FondaparinuxZileuton may increase the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumZileuton may increase the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
ForasartanThe risk or severity of adverse effects can be increased when Forasartan is combined with Zileuton.Experimental
FormestaneThe risk or severity of adverse effects can be increased when Zileuton is combined with Formestane.Approved, Investigational, Withdrawn
FosamprenavirThe metabolism of Zileuton can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Zileuton can be increased when it is combined with Fosaprepitant.Approved
FosinoprilThe risk or severity of adverse effects can be increased when Fosinopril is combined with Zileuton.Approved
FosphenytoinThe metabolism of Zileuton can be increased when combined with Fosphenytoin.Approved
FramycetinZileuton may decrease the excretion rate of Framycetin which could result in a higher serum level.Approved
FurosemideZileuton may decrease the diuretic activities of Furosemide.Approved, Vet Approved
Fusidic AcidThe serum concentration of Zileuton can be increased when it is combined with Fusidic Acid.Approved
GabexateZileuton may increase the anticoagulant activities of Gabexate.Investigational
GarenoxacinZileuton may increase the neuroexcitatory activities of Garenoxacin.Investigational
GatifloxacinZileuton may increase the neuroexcitatory activities of Gatifloxacin.Approved, Investigational
GemeprostThe therapeutic efficacy of Gemeprost can be decreased when used in combination with Zileuton.Approved, Withdrawn
GemfibrozilThe metabolism of Zileuton can be decreased when combined with Gemfibrozil.Approved
GemifloxacinZileuton may increase the neuroexcitatory activities of Gemifloxacin.Approved, Investigational
GeneticinZileuton may decrease the excretion rate of Geneticin which could result in a higher serum level.Experimental
GentamicinZileuton may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Vet Approved
GENTAMICIN C1AZileuton may decrease the excretion rate of GENTAMICIN C1A which could result in a higher serum level.Experimental
GPX-150Zileuton may decrease the excretion rate of GPX-150 which could result in a higher serum level.Investigational
GrepafloxacinZileuton may increase the neuroexcitatory activities of Grepafloxacin.Investigational, Withdrawn
GuacetisalThe risk or severity of adverse effects can be increased when Zileuton is combined with Guacetisal.Experimental
HalcinonideThe risk or severity of adverse effects can be increased when Zileuton is combined with Halcinonide.Approved, Investigational, Withdrawn
HaloperidolThe risk or severity of adverse effects can be increased when Zileuton is combined with Haloperidol.Approved
HE3286The risk or severity of adverse effects can be increased when Zileuton is combined with HE3286.Investigational
HeparinZileuton may increase the anticoagulant activities of Heparin.Approved, Investigational
HigenamineThe risk or severity of adverse effects can be increased when Zileuton is combined with Higenamine.Investigational
HydralazineZileuton may decrease the antihypertensive activities of Hydralazine.Approved
HydrochlorothiazideThe therapeutic efficacy of Hydrochlorothiazide can be decreased when used in combination with Zileuton.Approved, Vet Approved
HydrocortisoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Hydrocortisone.Approved, Vet Approved
HydroflumethiazideThe therapeutic efficacy of Hydroflumethiazide can be decreased when used in combination with Zileuton.Approved, Investigational
Hygromycin BZileuton may decrease the excretion rate of Hygromycin B which could result in a higher serum level.Vet Approved
IbandronateThe risk or severity of adverse effects can be increased when Zileuton is combined with Ibandronate.Approved, Investigational
IbuprofenThe risk or severity of adverse effects can be increased when Zileuton is combined with Ibuprofen.Approved
IbuproxamThe risk or severity of adverse effects can be increased when Zileuton is combined with Ibuproxam.Withdrawn
IcatibantThe risk or severity of adverse effects can be increased when Zileuton is combined with Icatibant.Approved
IdarubicinZileuton may decrease the excretion rate of Idarubicin which could result in a higher serum level.Approved
IdelalisibThe serum concentration of Zileuton can be increased when it is combined with Idelalisib.Approved
IdraparinuxZileuton may increase the anticoagulant activities of Idraparinux.Investigational
IloprostThe therapeutic efficacy of Iloprost can be decreased when used in combination with Zileuton.Approved, Investigational
ImatinibThe metabolism of Zileuton can be decreased when combined with Imatinib.Approved
ImidaprilThe risk or severity of adverse effects can be increased when Imidapril is combined with Zileuton.Investigational
Imidazole salicylateThe risk or severity of adverse effects can be increased when Zileuton is combined with Imidazole salicylate.Experimental
IndapamideThe therapeutic efficacy of Indapamide can be decreased when used in combination with Zileuton.Approved
IndenololZileuton may decrease the antihypertensive activities of Indenolol.Withdrawn
IndinavirThe metabolism of Zileuton can be decreased when combined with Indinavir.Approved
IndobufenThe risk or severity of adverse effects can be increased when Zileuton is combined with Indobufen.Investigational
IndomethacinThe risk or severity of adverse effects can be increased when Indomethacin is combined with Zileuton.Approved, Investigational
IndoprofenThe risk or severity of adverse effects can be increased when Zileuton is combined with Indoprofen.Withdrawn
INNO-206Zileuton may decrease the excretion rate of INNO-206 which could result in a higher serum level.Investigational
IrbesartanThe metabolism of Zileuton can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Zileuton can be decreased when combined with Isavuconazonium.Approved, Investigational
IsepamicinZileuton may decrease the excretion rate of Isepamicin which could result in a higher serum level.Experimental
IsoxicamThe risk or severity of adverse effects can be increased when Zileuton is combined with Isoxicam.Withdrawn
IsradipineThe metabolism of Zileuton can be decreased when combined with Isradipine.Approved
IstaroximeThe risk or severity of adverse effects can be increased when Zileuton is combined with Istaroxime.Investigational
ItraconazoleThe metabolism of Zileuton can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Zileuton can be increased when it is combined with Ivacaftor.Approved
KanamycinZileuton may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Investigational, Vet Approved
KebuzoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Kebuzone.Experimental
KetoconazoleThe metabolism of Zileuton can be decreased when combined with Ketoconazole.Approved, Investigational
KetoprofenThe risk or severity of adverse effects can be increased when Zileuton is combined with Ketoprofen.Approved, Vet Approved
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Zileuton.Approved
LabetalolZileuton may decrease the antihypertensive activities of Labetalol.Approved
LandiololZileuton may decrease the antihypertensive activities of Landiolol.Investigational
LatanoprostThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Zileuton.Approved, Investigational
Latanoprostene BunodThe therapeutic efficacy of Latanoprostene Bunod can be decreased when used in combination with Zileuton.Approved, Investigational
LeflunomideThe metabolism of Zileuton can be decreased when combined with Leflunomide.Approved, Investigational
LepirudinZileuton may increase the anticoagulant activities of Lepirudin.Approved
LetaxabanZileuton may increase the anticoagulant activities of Letaxaban.Investigational
LevobunololZileuton may decrease the antihypertensive activities of Levobunolol.Approved
LevofloxacinZileuton may increase the neuroexcitatory activities of Levofloxacin.Approved, Investigational
LidocaineThe metabolism of Zileuton can be decreased when combined with Lidocaine.Approved, Vet Approved
LimaprostThe therapeutic efficacy of Limaprost can be decreased when used in combination with Zileuton.Approved, Investigational
LisinoprilThe risk or severity of adverse effects can be increased when Lisinopril is combined with Zileuton.Approved, Investigational
LisofyllineThe risk or severity of adverse effects can be increased when Zileuton is combined with Lisofylline.Investigational
LithiumThe serum concentration of Lithium can be increased when it is combined with Zileuton.Approved
LobeglitazoneThe metabolism of Zileuton can be decreased when combined with Lobeglitazone.Approved, Investigational
LonazolacThe risk or severity of adverse effects can be increased when Zileuton is combined with Lonazolac.Experimental
LopinavirThe metabolism of Zileuton can be decreased when combined with Lopinavir.Approved
LornoxicamThe risk or severity of adverse effects can be increased when Zileuton is combined with Lornoxicam.Approved, Investigational
LosartanThe metabolism of Zileuton can be decreased when combined with Losartan.Approved
LoteprednolThe risk or severity of adverse effects can be increased when Zileuton is combined with Loteprednol.Approved
LovastatinThe metabolism of Zileuton can be decreased when combined with Lovastatin.Approved, Investigational
LoxapineThe risk or severity of adverse effects can be increased when Zileuton is combined with Loxapine.Approved
LoxoprofenThe risk or severity of adverse effects can be increased when Zileuton is combined with Loxoprofen.Approved, Investigational
LubiprostoneThe therapeutic efficacy of Lubiprostone can be decreased when used in combination with Zileuton.Approved, Investigational
LuliconazoleThe serum concentration of Zileuton can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Zileuton can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibThe risk or severity of adverse effects can be increased when Zileuton is combined with Lumiracoxib.Approved, Investigational
LuprostiolThe therapeutic efficacy of Luprostiol can be decreased when used in combination with Zileuton.Vet Approved
Magnesium salicylateThe risk or severity of adverse effects can be increased when Zileuton is combined with Magnesium salicylate.Approved
ManidipineThe metabolism of Zileuton can be decreased when combined with Manidipine.Approved, Investigational
MasoprocolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Zileuton.Approved, Investigational
ME-609The risk or severity of adverse effects can be increased when Zileuton is combined with ME-609.Investigational
Meclofenamic acidThe risk or severity of adverse effects can be increased when Zileuton is combined with Meclofenamic acid.Approved, Vet Approved
MedrysoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Medrysone.Approved
Mefenamic acidThe risk or severity of adverse effects can be increased when Zileuton is combined with Mefenamic acid.Approved
MelagatranZileuton may increase the anticoagulant activities of Melagatran.Experimental
MelengestrolThe risk or severity of adverse effects can be increased when Zileuton is combined with Melengestrol.Vet Approved
MeloxicamThe risk or severity of adverse effects can be increased when Zileuton is combined with Meloxicam.Approved, Vet Approved
MepindololZileuton may decrease the antihypertensive activities of Mepindolol.Experimental
MesalazineZileuton may increase the nephrotoxic activities of Mesalazine.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Zileuton is combined with Metamizole.Investigational, Withdrawn
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Zileuton.Approved
MethyclothiazideThe therapeutic efficacy of Methyclothiazide can be decreased when used in combination with Zileuton.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Zileuton is combined with Methylprednisolone.Approved, Vet Approved
MetipranololZileuton may decrease the antihypertensive activities of Metipranolol.Approved
MetolazoneThe therapeutic efficacy of Metolazone can be decreased when used in combination with Zileuton.Approved
MetoprololZileuton may decrease the antihypertensive activities of Metoprolol.Approved, Investigational
MetrizamideZileuton may decrease the excretion rate of Metrizamide which could result in a higher serum level.Approved
MexiletineThe metabolism of Zileuton can be decreased when combined with Mexiletine.Approved
MicronomicinZileuton may decrease the excretion rate of Micronomicin which could result in a higher serum level.Experimental
MidostaurinThe metabolism of Zileuton can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Zileuton can be increased when it is combined with Mifepristone.Approved, Investigational
MisoprostolThe therapeutic efficacy of Misoprostol can be decreased when used in combination with Zileuton.Approved
MitotaneThe serum concentration of Zileuton can be decreased when it is combined with Mitotane.Approved
MizoribineThe risk or severity of adverse effects can be increased when Zileuton is combined with Mizoribine.Investigational
MoexiprilThe risk or severity of adverse effects can be increased when Moexipril is combined with Zileuton.Approved
MofebutazoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Mofebutazone.Experimental
MometasoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Mometasone.Approved, Vet Approved
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Zileuton.Approved
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Zileuton.Approved, Investigational
Mycophenolic acidThe risk or severity of adverse effects can be increased when Zileuton is combined with Mycophenolic acid.Approved
NabumetoneThe risk or severity of adverse effects can be increased when Nabumetone is combined with Zileuton.Approved
NadololZileuton may decrease the antihypertensive activities of Nadolol.Approved
NadroparinZileuton may increase the anticoagulant activities of Nadroparin.Approved
NafamostatZileuton may increase the anticoagulant activities of Nafamostat.Approved, Investigational
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Zileuton.Approved
Nalidixic AcidZileuton may increase the neuroexcitatory activities of Nalidixic Acid.Approved, Investigational
NaproxenThe risk or severity of adverse effects can be increased when Zileuton is combined with Naproxen.Approved, Vet Approved
NCX 1022The risk or severity of adverse effects can be increased when Zileuton is combined with NCX 1022.Investigational
NeamineZileuton may decrease the excretion rate of Neamine which could result in a higher serum level.Experimental
NebivololZileuton may decrease the antihypertensive activities of Nebivolol.Approved, Investigational
NefazodoneThe metabolism of Zileuton can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Zileuton can be decreased when combined with Nelfinavir.Approved
NemonoxacinZileuton may increase the neuroexcitatory activities of Nemonoxacin.Investigational
NeomycinZileuton may decrease the excretion rate of Neomycin which could result in a higher serum level.Approved, Vet Approved
NepafenacThe risk or severity of adverse effects can be increased when Nepafenac is combined with Zileuton.Approved
NetilmicinZileuton may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved, Investigational
NetupitantThe serum concentration of Zileuton can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Zileuton can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Zileuton can be decreased when combined with Nicardipine.Approved
NifenazoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Nifenazone.Experimental
Niflumic AcidThe risk or severity of adverse effects can be increased when Zileuton is combined with Niflumic Acid.Approved
NilotinibThe metabolism of Zileuton can be decreased when combined with Nilotinib.Approved, Investigational
NimesulideThe risk or severity of adverse effects can be increased when Zileuton is combined with Nimesulide.Approved, Investigational, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Zileuton is combined with Nitroaspirin.Investigational
NorfloxacinZileuton may increase the neuroexcitatory activities of Norfloxacin.Approved
OlaparibThe metabolism of Zileuton can be decreased when combined with Olaparib.Approved
Oleoyl-estroneThe risk or severity of adverse effects can be increased when Zileuton is combined with Oleoyl-estrone.Investigational
OlmesartanThe risk or severity of adverse effects can be increased when Olmesartan is combined with Zileuton.Approved, Investigational
OlopatadineThe risk or severity of adverse effects can be increased when Zileuton is combined with Olopatadine.Approved
OlsalazineZileuton may increase the nephrotoxic activities of Olsalazine.Approved
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Zileuton is combined with Omacetaxine mepesuccinate.Approved
OmapatrilatThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Zileuton.Investigational
OmeprazoleThe metabolism of Zileuton can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OrgoteinThe risk or severity of adverse effects can be increased when Zileuton is combined with Orgotein.Vet Approved
OsimertinibThe serum concentration of Zileuton can be increased when it is combined with Osimertinib.Approved
OtamixabanZileuton may increase the anticoagulant activities of Otamixaban.Investigational
OxaprozinThe risk or severity of adverse effects can be increased when Zileuton is combined with Oxaprozin.Approved
Oxolinic acidZileuton may increase the neuroexcitatory activities of Oxolinic acid.Experimental
OxprenololZileuton may decrease the antihypertensive activities of Oxprenolol.Approved
OxyphenbutazoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Oxyphenbutazone.Approved, Withdrawn
PalbociclibThe serum concentration of Zileuton can be increased when it is combined with Palbociclib.Approved
PamidronateThe risk or severity of adverse effects can be increased when Zileuton is combined with Pamidronate.Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Paramethasone.Approved
ParecoxibThe risk or severity of adverse effects can be increased when Zileuton is combined with Parecoxib.Approved
ParomomycinZileuton may decrease the excretion rate of Paromomycin which could result in a higher serum level.Approved, Investigational
ParthenolideThe risk or severity of adverse effects can be increased when Zileuton is combined with Parthenolide.Investigational
PazufloxacinZileuton may increase the neuroexcitatory activities of Pazufloxacin.Investigational
PefloxacinZileuton may increase the neuroexcitatory activities of Pefloxacin.Approved
Peginterferon alfa-2bThe serum concentration of Zileuton can be increased when it is combined with Peginterferon alfa-2b.Approved
PenbutololZileuton may decrease the antihypertensive activities of Penbutolol.Approved, Investigational
Pentaerythritol TetranitrateZileuton may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
PentobarbitalThe metabolism of Zileuton can be increased when combined with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateZileuton may increase the anticoagulant activities of Pentosan Polysulfate.Approved
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Zileuton.Approved
PhenindioneZileuton may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenobarbitalThe metabolism of Zileuton can be increased when combined with Phenobarbital.Approved
PhenprocoumonZileuton may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenylbutazoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Phenylbutazone.Approved, Vet Approved
PhenytoinThe metabolism of Zileuton can be increased when combined with Phenytoin.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Zileuton.Approved, Investigational
PimozideThe serum concentration of Pimozide can be increased when it is combined with Zileuton.Approved
PindololZileuton may decrease the antihypertensive activities of Pindolol.Approved
Pipemidic acidZileuton may increase the neuroexcitatory activities of Pipemidic acid.Experimental
PirarubicinZileuton may decrease the excretion rate of Pirarubicin which could result in a higher serum level.Investigational
PiretanideZileuton may decrease the diuretic activities of Piretanide.Experimental
PirfenidoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Pirfenidone.Approved, Investigational
Piromidic acidZileuton may increase the neuroexcitatory activities of Piromidic acid.Experimental
PiroxicamThe risk or severity of adverse effects can be increased when Piroxicam is combined with Zileuton.Approved, Investigational
PirprofenThe risk or severity of adverse effects can be increased when Zileuton is combined with Pirprofen.Experimental
Platelet Activating FactorZileuton may decrease the antihypertensive activities of Platelet Activating Factor.Experimental
PlazomicinZileuton may decrease the excretion rate of Plazomicin which could result in a higher serum level.Investigational
PlicamycinZileuton may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational, Withdrawn
PolythiazideThe therapeutic efficacy of Polythiazide can be decreased when used in combination with Zileuton.Approved
PosaconazoleThe metabolism of Zileuton can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PractololZileuton may decrease the antihypertensive activities of Practolol.Approved
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Zileuton.Approved
PranoprofenThe risk or severity of adverse effects can be increased when Zileuton is combined with Pranoprofen.Experimental, Investigational
PrasteroneThe risk or severity of adverse effects can be increased when Zileuton is combined with Prasterone.Approved, Nutraceutical
Prasterone sulfateThe risk or severity of adverse effects can be increased when Zileuton is combined with Prasterone sulfate.Investigational
PrednicarbateThe risk or severity of adverse effects can be increased when Zileuton is combined with Prednicarbate.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Zileuton is combined with Prednisolone.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Prednisone.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Zileuton is combined with Pregnenolone.Experimental, Investigational
PrimidoneThe metabolism of Zileuton can be increased when combined with Primidone.Approved, Vet Approved
ProbenecidThe serum concentration of Zileuton can be increased when it is combined with Probenecid.Approved
ProglumetacinThe risk or severity of adverse effects can be increased when Zileuton is combined with Proglumetacin.Experimental
PropacetamolThe risk or severity of adverse effects can be increased when Zileuton is combined with Propacetamol.Approved, Investigational
PropranololThe serum concentration of Propranolol can be increased when it is combined with Zileuton.Approved, Investigational
PropyphenazoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Propyphenazone.Experimental
ProquazoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Proquazone.Experimental
Prostaglandin B2The therapeutic efficacy of Prostaglandin B2 can be decreased when used in combination with Zileuton.Experimental
Prostaglandin G2The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Zileuton.Experimental
ProstaleneThe therapeutic efficacy of Prostalene can be decreased when used in combination with Zileuton.Vet Approved
Protein CZileuton may increase the anticoagulant activities of Protein C.Approved
Protein S humanZileuton may increase the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeZileuton may increase the anticoagulant activities of Protocatechualdehyde.Approved
PrulifloxacinZileuton may increase the neuroexcitatory activities of Prulifloxacin.Investigational
PTC299The risk or severity of adverse effects can be increased when Zileuton is combined with PTC299.Investigational
PuromycinZileuton may decrease the excretion rate of Puromycin which could result in a higher serum level.Experimental
PyrimethamineThe metabolism of Zileuton can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinaprilThe risk or severity of adverse effects can be increased when Quinapril is combined with Zileuton.Approved, Investigational
QuinethazoneThe therapeutic efficacy of Quinethazone can be decreased when used in combination with Zileuton.Approved
QuinineThe metabolism of Zileuton can be decreased when combined with Quinine.Approved
RamiprilThe risk or severity of adverse effects can be increased when Ramipril is combined with Zileuton.Approved
RanolazineThe metabolism of Zileuton can be decreased when combined with Ranolazine.Approved, Investigational
RescinnamineThe risk or severity of adverse effects can be increased when Rescinnamine is combined with Zileuton.Approved
ResveratrolThe risk or severity of adverse effects can be increased when Zileuton is combined with Resveratrol.Approved, Experimental, Investigational
ReviparinZileuton may increase the anticoagulant activities of Reviparin.Approved, Investigational
RibostamycinZileuton may decrease the excretion rate of Ribostamycin which could result in a higher serum level.Approved, Investigational
RifabutinThe metabolism of Zileuton can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Zileuton can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Zileuton can be increased when combined with Rifapentine.Approved
RimexoloneThe risk or severity of adverse effects can be increased when Zileuton is combined with Rimexolone.Approved
RisedronateThe risk or severity of adverse effects can be increased when Zileuton is combined with Risedronate.Approved, Investigational
RivaroxabanZileuton may increase the anticoagulant activities of Rivaroxaban.Approved
RofecoxibThe risk or severity of adverse effects can be increased when Rofecoxib is combined with Zileuton.Investigational, Withdrawn
RopiniroleThe metabolism of Zileuton can be decreased when combined with Ropinirole.Approved, Investigational
RosoxacinZileuton may increase the neuroexcitatory activities of Rosoxacin.Approved, Investigational
RufloxacinZileuton may increase the neuroexcitatory activities of Rufloxacin.Experimental
SabarubicinZileuton may decrease the excretion rate of Sabarubicin which could result in a higher serum level.Investigational
SacubitrilThe risk or severity of adverse effects can be increased when Sacubitril is combined with Zileuton.Approved
SalicylamideThe risk or severity of adverse effects can be increased when Zileuton is combined with Salicylamide.Approved
Salicylic acidThe risk or severity of adverse effects can be increased when Zileuton is combined with Salicylic acid.Approved, Vet Approved
SalsalateThe risk or severity of adverse effects can be increased when Zileuton is combined with Salsalate.Approved
SaprisartanThe risk or severity of adverse effects can be increased when Saprisartan is combined with Zileuton.Experimental
SaquinavirThe metabolism of Zileuton can be decreased when combined with Saquinavir.Approved, Investigational
SaralasinThe risk or severity of adverse effects can be increased when Saralasin is combined with Zileuton.Investigational
SecobarbitalThe metabolism of Zileuton can be increased when combined with Secobarbital.Approved, Vet Approved
SemapimodThe risk or severity of adverse effects can be increased when Zileuton is combined with Semapimod.Investigational
SeratrodastThe risk or severity of adverse effects can be increased when Zileuton is combined with Seratrodast.Approved
SerrapeptaseThe risk or severity of adverse effects can be increased when Zileuton is combined with Serrapeptase.Investigational
SildenafilThe metabolism of Zileuton can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Zileuton can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Zileuton can be increased when it is combined with Simeprevir.Approved
SisomicinZileuton may decrease the excretion rate of Sisomicin which could result in a higher serum level.Investigational
SitafloxacinZileuton may increase the neuroexcitatory activities of Sitafloxacin.Experimental, Investigational
Sodium phosphateSodium phosphate may increase the nephrotoxic activities of Zileuton.Approved
SorafenibThe metabolism of Zileuton can be decreased when combined with Sorafenib.Approved, Investigational
SotalolZileuton may decrease the antihypertensive activities of Sotalol.Approved
SP1049CZileuton may decrease the excretion rate of SP1049C which could result in a higher serum level.Investigational
SparfloxacinZileuton may increase the neuroexcitatory activities of Sparfloxacin.Approved, Investigational
SpectinomycinZileuton may decrease the excretion rate of Spectinomycin which could result in a higher serum level.Approved, Investigational, Vet Approved
SpiraprilThe risk or severity of adverse effects can be increased when Spirapril is combined with Zileuton.Approved
SpironolactoneZileuton may decrease the antihypertensive activities of Spironolactone.Approved
SRT501The risk or severity of adverse effects can be increased when Zileuton is combined with SRT501.Investigational
St. John's WortThe serum concentration of Zileuton can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Zileuton can be increased when it is combined with Stiripentol.Approved
StreptomycinZileuton may decrease the excretion rate of Streptomycin which could result in a higher serum level.Approved, Vet Approved
StreptozocinZileuton may decrease the excretion rate of Streptozocin which could result in a higher serum level.Approved
SulfadiazineThe metabolism of Zileuton can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Zileuton can be decreased when combined with Sulfamethoxazole.Approved
SulfasalazineThe risk or severity of adverse effects can be increased when Zileuton is combined with Sulfasalazine.Approved
SulfisoxazoleThe metabolism of Zileuton can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulindacThe risk or severity of adverse effects can be increased when Sulindac is combined with Zileuton.Approved
SulodexideZileuton may increase the anticoagulant activities of Sulodexide.Approved, Investigational
SulprostoneThe therapeutic efficacy of Sulprostone can be decreased when used in combination with Zileuton.Investigational
SuprofenThe risk or severity of adverse effects can be increased when Zileuton is combined with Suprofen.Approved, Withdrawn
SuxibuzoneThe risk or severity of adverse effects can be increased when Zileuton is combined with Suxibuzone.Experimental
TacrolimusZileuton may increase the nephrotoxic activities of Tacrolimus.Approved, Investigational
TafluprostThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Zileuton.Approved
TalinololZileuton may decrease the antihypertensive activities of Talinolol.Investigational
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Zileuton.Approved
TarenflurbilThe risk or severity of adverse effects can be increased when Zileuton is combined with Tarenflurbil.Investigational
TasosartanThe risk or severity of adverse effects can be increased when Tasosartan is combined with Zileuton.Approved
Technetium Tc-99m etidronateThe risk or severity of adverse effects can be increased when Zileuton is combined with Technetium Tc-99m etidronate.Approved
Technetium Tc-99m medronateThe risk or severity of adverse effects can be increased when Zileuton is combined with Technetium Tc-99m medronate.Approved
TelaprevirThe metabolism of Zileuton can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Zileuton can be decreased when combined with Telithromycin.Approved
TelmisartanThe risk or severity of adverse effects can be increased when Telmisartan is combined with Zileuton.Approved, Investigational
TemafloxacinZileuton may increase the neuroexcitatory activities of Temafloxacin.Withdrawn
TemocaprilThe risk or severity of adverse effects can be increased when Temocapril is combined with Zileuton.Experimental, Investigational
TenidapThe risk or severity of adverse effects can be increased when Zileuton is combined with Tenidap.Experimental
Tenofovir disoproxilThe risk or severity of adverse effects can be increased when Zileuton is combined with Tenofovir disoproxil.Approved, Investigational
TenoxicamThe risk or severity of adverse effects can be increased when Tenoxicam is combined with Zileuton.Approved
TepoxalinThe risk or severity of adverse effects can be increased when Zileuton is combined with Tepoxalin.Vet Approved
TeriflunomideThe serum concentration of Zileuton can be decreased when it is combined with Teriflunomide.Approved
TertatololZileuton may decrease the antihypertensive activities of Tertatolol.Experimental
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Zileuton.Approved
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Zileuton is combined with Tiaprofenic acid.Approved
TicagrelorThe metabolism of Zileuton can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Zileuton can be decreased when combined with Ticlopidine.Approved
Tiludronic acidThe risk or severity of adverse effects can be increased when Zileuton is combined with Tiludronic acid.Approved, Investigational, Vet Approved
TimololZileuton may decrease the antihypertensive activities of Timolol.Approved
TinoridineThe risk or severity of adverse effects can be increased when Zileuton is combined with Tinoridine.Investigational
TixocortolThe risk or severity of adverse effects can be increased when Zileuton is combined with Tixocortol.Approved
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Zileuton.Approved
TobramycinZileuton may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
TocilizumabThe serum concentration of Zileuton can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Zileuton can be decreased when combined with Tolbutamide.Approved
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Zileuton is combined with Tolfenamic Acid.Approved
TolmetinThe risk or severity of adverse effects can be increased when Tolmetin is combined with Zileuton.Approved
TopiroxostatThe metabolism of Zileuton can be decreased when combined with Topiroxostat.Approved, Investigational
TorasemideZileuton may decrease the diuretic activities of Torasemide.Approved
TrandolaprilThe risk or severity of adverse effects can be increased when Trandolapril is combined with Zileuton.Approved
TranilastThe risk or severity of adverse effects can be increased when Zileuton is combined with Tranilast.Approved, Investigational
TravoprostThe therapeutic efficacy of Travoprost can be decreased when used in combination with Zileuton.Approved
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Zileuton.Approved, Investigational
TriamcinoloneThe risk or severity of adverse effects can be increased when Zileuton is combined with Triamcinolone.Approved, Vet Approved
TriamtereneZileuton may decrease the antihypertensive activities of Triamterene.Approved
TribenosideThe risk or severity of adverse effects can be increased when Zileuton is combined with Tribenoside.Experimental
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Zileuton.Approved, Vet Approved
TrimethoprimThe metabolism of Zileuton can be decreased when combined with Trimethoprim.Approved, Vet Approved
TriptolideThe risk or severity of adverse effects can be increased when Zileuton is combined with Triptolide.Investigational
TrovafloxacinZileuton may increase the neuroexcitatory activities of Trovafloxacin.Approved, Investigational, Withdrawn
TroxerutinZileuton may increase the anticoagulant activities of Troxerutin.Investigational
UlobetasolThe risk or severity of adverse effects can be increased when Zileuton is combined with Ulobetasol.Approved
UnoprostoneThe therapeutic efficacy of Unoprostone can be decreased when used in combination with Zileuton.Approved
ValdecoxibThe risk or severity of adverse effects can be increased when Valdecoxib is combined with Zileuton.Investigational, Withdrawn
Valproic AcidThe metabolism of Zileuton can be decreased when combined with Valproic Acid.Approved, Investigational
ValrubicinZileuton may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
ValsartanThe metabolism of Zileuton can be decreased when combined with Valsartan.Approved, Investigational
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Zileuton.Approved
VemurafenibThe serum concentration of Zileuton can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Zileuton can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Zileuton can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Zileuton can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Zileuton.Approved
XimelagatranZileuton may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
ZafirlukastThe metabolism of Zileuton can be decreased when combined with Zafirlukast.Approved, Investigational
ZaltoprofenThe risk or severity of adverse effects can be increased when Zileuton is combined with Zaltoprofen.Approved, Investigational
ZiprasidoneThe metabolism of Zileuton can be decreased when combined with Ziprasidone.Approved
ZofenoprilThe risk or severity of adverse effects can be increased when Zofenopril is combined with Zileuton.Experimental
Zoledronic acidThe risk or severity of adverse effects can be increased when Zileuton is combined with Zoledronic acid.Approved
ZomepiracThe risk or severity of adverse effects can be increased when Zileuton is combined with Zomepirac.Withdrawn
Zoptarelin doxorubicinZileuton may decrease the excretion rate of Zoptarelin doxorubicin which could result in a higher serum level.Investigational
ZorubicinZileuton may decrease the excretion rate of Zorubicin which could result in a higher serum level.Experimental
ZucapsaicinThe metabolism of Zileuton can be decreased when combined with Zucapsaicin.Approved
Food Interactions
Not Available

References

Synthesis Reference

Emanuele ATTOLINA, Gianmaria Dell'Anna, Roberto Rossi, Pietro Allegrini, Gabriele Razzetti, "PROCESS FOR THE PREPARATION OF ZILEUTON." U.S. Patent US20090286996, issued November 19, 2009.

US20090286996
General References
  1. Berger W, De Chandt MT, Cairns CB: Zileuton: clinical implications of 5-Lipoxygenase inhibition in severe airway disease. Int J Clin Pract. 2007 Apr;61(4):663-76. [PubMed:17394438]
  2. Wenzel SE, Kamada AK: Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma. Ann Pharmacother. 1996 Jul-Aug;30(7-8):858-64. [PubMed:8826571]
  3. Malo PE, Bell RL, Shaughnessy TK, Summers JB, Brooks DW, Carter GW: The 5-lipoxygenase inhibitory activity of zileuton in in vitro and in vivo models of antigen-induced airway anaphylaxis. Pulm Pharmacol. 1994 Apr;7(2):73-9. [PubMed:8081074]
External Links
Human Metabolome Database
HMDB14882
KEGG Drug
D00414
PubChem Compound
60490
PubChem Substance
46506394
ChemSpider
54531
BindingDB
50000541
ChEBI
10112
ChEMBL
CHEMBL93
Therapeutic Targets Database
DAP000591
PharmGKB
PA451955
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Zileuton
FDA label
Download (129 KB)
MSDS
Download (14.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceLung Inflammation1
1CompletedTreatmentSickle Cell Disorders1
1TerminatedTreatmentChronic Myelogenous Leukemia (CML)2
1, 2CompletedPreventionTobacco Use Disorders1
1, 2CompletedTreatmentAsthma Bronchial1
1, 2TerminatedTreatmentAlbinism, Oculocutaneous / Hermansky-Pudlak Syndrome (HPS) / Metabolic Diseases / Platelet Storage Pool Deficiency / Pulmonary Fibrosis1
2CompletedPreventionHead and Neck Carcinoma / Lung Cancers1
2CompletedTreatmentAsthma Bronchial2
2CompletedTreatmentIdiopathic Pulmonary Fibrosis (IPF)1
2CompletedTreatmentLung Cancers1
2RecruitingPreventionMultiple Pulmonary Nodules / Pulmonary Nodules / Tobacco Use Disorders1
2Unknown StatusTreatmentAcne Vulgaris1
3TerminatedTreatmentPulmonary Disease, Chronic Obstructive1
4CompletedTreatmentAsthma Bronchial2
4TerminatedTreatmentAsthma Bronchial1

Pharmacoeconomics

Manufacturers
  • Cornerstone therapeutics inc
Packagers
Dosage forms
FormRouteStrength
Tablet, extended releaseOral600 mg/1
TabletOral600 mg/1
Tablet, multilayer, extended releaseOral600 mg/1
Prices
Unit descriptionCostUnit
Zyflo 600 mg tablet6.49USD tablet
Zyflo CR 600 mg 12 Hour tablet6.23USD tablet
Zyflo 600 mg filmtab5.99USD tablet
Zyflo cr 600 mg tablet5.99USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5422123No1995-06-062012-06-06Us
US4873259No1993-12-092010-12-09Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)144.2-145.2 °CNot Available
water solubilityPractically insoluble (0.5 mg/ml)Not Available
logP0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0539 mg/mLALOGPS
logP2.01ALOGPS
logP2.01ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.84ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.56 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.96 m3·mol-1ChemAxon
Polarizability24.14 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9915
Blood Brain Barrier+0.8846
Caco-2 permeable-0.5793
P-glycoprotein substrateNon-substrate0.6789
P-glycoprotein inhibitor INon-inhibitor0.9684
P-glycoprotein inhibitor IINon-inhibitor0.9765
Renal organic cation transporterNon-inhibitor0.9583
CYP450 2C9 substrateNon-substrate0.5907
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6384
CYP450 1A2 substrateInhibitor0.5318
CYP450 2C9 inhibitorNon-inhibitor0.7975
CYP450 2D6 inhibitorNon-inhibitor0.8866
CYP450 2C19 inhibitorNon-inhibitor0.6451
CYP450 3A4 inhibitorNon-inhibitor0.7062
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5821
Ames testAMES toxic0.5865
CarcinogenicityNon-carcinogens0.7968
BiodegradationNot ready biodegradable0.985
Rat acute toxicity2.2646 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9884
hERG inhibition (predictor II)Non-inhibitor0.9051
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiophenes
Sub Class
1-benzothiophenes
Direct Parent
1-benzothiophenes
Alternative Parents
2,3,5-trisubstituted thiophenes / Benzenoids / Heteroaromatic compounds / Organic carbonic acids and derivatives / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
1-benzothiophene / 2,3,5-trisubstituted thiophene / Benzenoid / Heteroaromatic compound / Thiophene / Carbonic acid derivative / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
ureas, 1-benzothiophenes (CHEBI:10112)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Iron ion binding
Specific Function
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name
ALOX5
Uniprot ID
P09917
Uniprot Name
Arachidonate 5-lipoxygenase
Molecular Weight
77982.595 Da
References
  1. Wenzel SE: Leukotriene receptor antagonists and related compounds. Can Respir J. 1999 Mar-Apr;6(2):189-93. [PubMed:10322101]
  2. Hardy DB, Pereria LE, Yang K: Prostaglandins and leukotriene B4 are potent inhibitors of 11beta-hydroxysteroid dehydrogenase type 2 activity in human choriocarcinoma JEG-3 cells. Biol Reprod. 1999 Jul;61(1):40-5. [PubMed:10377029]
  3. Yamashita M, Kushihara M, Hirasawa N, Takasaki W, Takahagi H, Takayanagi M, Ohuchi K: Inhibition by troglitazone of the antigen-induced production of leukotrienes in immunoglobulin E-sensitized RBL-2H3 cells. Br J Pharmacol. 2000 Jan;129(2):367-73. [PubMed:10694244]
  4. Qian C, Hwang SB, Libertine-Garahan L, Eckman JB, Cai X, Scannell RT, Yeh CG: Anti-inflammatory activities of LDP-392, a dual PAF receptor antagonist and 5-lipoxygenase inhibitor. Pharmacol Res. 2001 Sep;44(3):213-20. [PubMed:11529688]
  5. Coffey MJ, Phare SM, Peters-Golden M: Peroxynitrite-induced nitrotyrosination of proteins is blocked by direct 5-lipoxygenase inhibitor zileuton. J Pharmacol Exp Ther. 2001 Oct;299(1):198-203. [PubMed:11561080]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. Zouboulis CC: Zileuton, a new efficient and safe systemic anti-acne drug. Dermatoendocrinol. 2009 May;1(3):188-92. [PubMed:20436887]
  8. Zouboulis CC, Seltmann H, Alestas T: Zileuton prevents the activation of the leukotriene pathway and reduces sebaceous lipogenesis. Exp Dermatol. 2010 Feb;19(2):148-50. doi: 10.1111/j.1600-0625.2009.00929.x. Epub 2009 Jul 23. [PubMed:19645854]
  9. Berger W, De Chandt MT, Cairns CB: Zileuton: clinical implications of 5-Lipoxygenase inhibition in severe airway disease. Int J Clin Pract. 2007 Apr;61(4):663-76. [PubMed:17394438]
  10. Guidot DM, Repine MJ, Westcott JY, Repine JE: Intrinsic 5-lipoxygenase activity is required for neutrophil responsivity. Proc Natl Acad Sci U S A. 1994 Aug 16;91(17):8156-9. [PubMed:8058773]
  11. Wenzel SE, Kamada AK: Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma. Ann Pharmacother. 1996 Jul-Aug;30(7-8):858-64. [PubMed:8826571]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Details
2. Cytochrome P450 1A2
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  3. Machinist JM, Mayer MD, Shet MS, Ferrero JL, Rodrigues AD: Identification of the human liver cytochrome P450 enzymes involved in the metabolism of zileuton (ABT-077) and its N-dehydroxylated metabolite, Abbott-66193. Drug Metab Dispos. 1995 Oct;23(10):1163-74. [PubMed:8654206]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Machinist JM, Mayer MD, Shet MS, Ferrero JL, Rodrigues AD: Identification of the human liver cytochrome P450 enzymes involved in the metabolism of zileuton (ABT-077) and its N-dehydroxylated metabolite, Abbott-66193. Drug Metab Dispos. 1995 Oct;23(10):1163-74. [PubMed:8654206]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Li F, Chordia MD, Woodling KA, Macdonald TL: Irreversible alkylation of human serum albumin by zileuton metabolite 2-acetylbenzothiophene-S-oxide: a potential model for hepatotoxicity. Chem Res Toxicol. 2007 Dec;20(12):1854-61. Epub 2007 Oct 19. [PubMed:17944539]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:42