Details of the Drug

General Information of Drug (ID: DMVRIC2)

Drug Name
Zileuton
Synonyms
Leutrol; Zileutonum; Ziluton; Zyflo; Abbott brand of zileuton; Zyflo CR; Zyflo Filmtab; A 64077; Abbot 64077; Abbott 64077; A-64077; ABBOTT-64077; ABT-077; CTI-02; ZYFLO (TN); ZYFLO, Zileuton; Zileutonum [INN-Latin]; Zyflo (TN); Zileuton (USP/INN); Zileuton [USAN:INN:BAN]; N-[1-(benzo[b]thiophen-2-yl)ethyl]-N-hydroxyurea; N-(1-Benzo(b)thien-2-ylethyl)-N-hydroxyurea; (+-)-1-(1-Benzo(b)thien-2-ylethyl)-1-hydroxyurea; (+-)-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea; (+/-)-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea; 1-[1-(1-benzothien-2-yl)ethyl]-1-hydroxyurea; 1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
Indication
Disease Entry ICD 11 Status REF
Asthma CA23 Approved [1], [2]
Therapeutic Class
Antiinflammatory Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 236.29
Topological Polar Surface Area (xlogp) 1.6
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Absorption
The drug is rapidly and almost completely absorbed [3]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Clearance
The apparent oral clearance of drug is 7 mL/min/kg [5]
Half-life
The concentration or amount of drug in body reduced by one-half in 2.5 hours [6]
Metabolism
The drug is metabolized via the hepatic [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 169.28029 micromolar/kg/day [7]
Vd
The volume of distribution (Vd) of drug is 1.2 L/kg [5]
Water Solubility
The ability of drug to dissolve in water is measured as 0.5 mg/mL [4]
Chemical Identifiers
Formula
C11H12N2O2S
IUPAC Name
1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
Canonical SMILES
CC(C1=CC2=CC=CC=C2S1)N(C(=O)N)O
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)
InChIKey
MWLSOWXNZPKENC-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
60490
ChEBI ID
CHEBI:10112
CAS Number
111406-87-2
DrugBank ID
DB00744
TTD ID
D09JUG
INTEDE ID
DR1730
ACDINA ID
D00740

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Arachidonate 5-lipoxygenase (5-LOX) TT2J34L LOX5_HUMAN Inhibitor [8], [9], [10], [11], [12], [13]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [14]
Cytochrome P450 2C9 (CYP2C9)
Main DME 		DE5IED8 CP2C9_HUMAN Substrate [15]
Cytochrome P450 1A2 (CYP1A2)
Main DME 		DEJGDUW CP1A2_HUMAN Substrate [16]
Prostaglandin G/H synthase 1 (COX-1) DE073H6 PGH1_HUMAN Substrate [14]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Asthma
ICD Disease Classification CA23
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Arachidonate 5-lipoxygenase (5-LOX) DTT ALOX5 4.15E-01 -0.06 -0.15
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 4.89E-02 -3.74E-01 -6.96E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 4.97E-04 -1.04E+00 -1.67E+00
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.10E-01 -1.23E-01 -2.88E-01
Prostaglandin G/H synthase 1 (COX-1) DME PTGS1 4.46E-01 -5.00E-02 -3.97E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Zileuton
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Aminophylline DML2NIB Moderate Decreased metabolism of Zileuton caused by Aminophylline mediated inhibition of CYP450 enzyme. Asthma [CA23] [59]
Roflumilast DMPGHY8 Moderate Decreased metabolism of Zileuton caused by Roflumilast mediated inhibition of CYP450 enzyme. Asthma [CA23] [60]
Coadministration of a Drug Treating the Disease Different from Zileuton (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Arn-509 DMT81LZ Moderate Increased metabolism of Zileuton caused by Arn-509 mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [60]
Bepridil DM0RKS4 Minor Decreased metabolism of Zileuton caused by Bepridil mediated inhibition of CYP450 enzyme. Angina pectoris [BA40] [61]
Nifedipine DMSVOZT Minor Decreased metabolism of Zileuton caused by Nifedipine mediated inhibition of CYP450 enzyme. Angina pectoris [BA40] [61]
Bedaquiline DM3906J Moderate Increased risk of hepatotoxicity by the combination of Zileuton and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [62]
Obeticholic acid DM3Q1SM Moderate Decreased metabolism of Zileuton caused by Obeticholic acid mediated inhibition of CYP450 enzyme. Autoimmune liver disease [DB96] [63]
Dalfopristin DM4LTKV Moderate Decreased metabolism of Zileuton caused by Dalfopristin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [64]
Telithromycin DMZ4P3A Moderate Decreased metabolism of Zileuton caused by Telithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [65]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Zileuton and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [66]
Lapatinib DM3BH1Y Moderate Decreased metabolism of Zileuton caused by Lapatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [67]
Tucatinib DMBESUA Moderate Decreased metabolism of Zileuton caused by Tucatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [68]
Alpelisib DMEXMYK Moderate Increased metabolism of Zileuton caused by Alpelisib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [69]
Levobupivacaine DM783CH Moderate Decreased metabolism of Zileuton caused by Levobupivacaine mediated inhibition of CYP450 enzyme. Corneal disease [9A76-9A78] [60]
Oxtriphylline DMLHSE3 Moderate Decreased metabolism of Zileuton caused by Oxtriphylline mediated inhibition of CYP450 enzyme. Cough [MD12] [59]
Mifepristone DMGZQEF Moderate Decreased metabolism of Zileuton caused by Mifepristone mediated inhibition of CYP450 enzyme. Cushing syndrome [5A70] [70]
Osilodrostat DMIJC9X Moderate Decreased metabolism of Zileuton caused by Osilodrostat mediated inhibition of CYP450 enzyme. Cushing syndrome [5A70] [71]
Ivacaftor DMZC1HS Moderate Decreased metabolism of Zileuton caused by Ivacaftor mediated inhibition of CYP450 enzyme. Cystic fibrosis [CA25] [72]
Nefazodone DM4ZS8M Moderate Decreased metabolism of Zileuton caused by Nefazodone mediated inhibition of CYP450 enzyme. Depression [6A70-6A7Z] [73]
PMID28870136-Compound-49 DMTUC9E Moderate Decreased metabolism of Zileuton caused by PMID28870136-Compound-49 mediated inhibition of CYP450 enzyme. Discovery agent [N.A.] [74]
Cenobamate DMGOVHA Moderate Increased metabolism of Zileuton caused by Cenobamate mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [75]
Stiripentol DMMSDOY Moderate Decreased metabolism of Zileuton caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [60]
Cannabidiol DM0659E Moderate Increased risk of hepatotoxicity by the combination of Zileuton and Cannabidiol. Epileptic encephalopathy [8A62] [60]
Itraconazole DMCR1MV Moderate Decreased metabolism of Zileuton caused by Itraconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [76]
Carvedilol DMHTEAO Moderate Decreased metabolism of Zileuton caused by Carvedilol. Heart failure [BD10-BD1Z] [61]
Rifapentine DMCHV4I Moderate Increased metabolism of Zileuton caused by Rifapentine mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [77]
Saquinavir DMG814N Moderate Decreased metabolism of Zileuton caused by Saquinavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [78]
Etravirine DMGV8QU Moderate Increased metabolism of Zileuton caused by Etravirine mediated induction of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [79]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Zileuton and Mipomersen. Hyper-lipoproteinaemia [5C80] [80]
Teriflunomide DMQ2FKJ Major Increased risk of hepatotoxicity by the combination of Zileuton and Teriflunomide. Hyper-lipoproteinaemia [5C80] [81]
BMS-201038 DMQTAGO Major Increased risk of hepatotoxicity by the combination of Zileuton and BMS-201038. Hyper-lipoproteinaemia [5C80] [82]
Acebutolol DM0TI4U Moderate Decreased metabolism of Zileuton caused by Acebutolol. Hypertension [BA00-BA04] [61]
Penbutolol DM4ES8F Moderate Decreased metabolism of Zileuton caused by Penbutolol. Hypertension [BA00-BA04] [61]
Nebivolol DM7F1PA Moderate Decreased metabolism of Zileuton caused by Nebivolol. Hypertension [BA00-BA04] [61]
Levamlodipine DM92S6N Minor Decreased metabolism of Zileuton caused by Levamlodipine mediated inhibition of CYP450 enzyme. Hypertension [BA00-BA04] [61]
Pindolol DMD2NV7 Moderate Decreased metabolism of Zileuton caused by Pindolol. Hypertension [BA00-BA04] [61]
Conivaptan DM1V329 Moderate Decreased metabolism of Zileuton caused by Conivaptan mediated inhibition of CYP450 enzyme. Hypo-osmolality/hyponatraemia [5C72] [83]
Pirfenidone DM6VZFQ Moderate Decreased metabolism of Zileuton caused by Pirfenidone mediated inhibition of CYP450 enzyme. Idiopathic interstitial pneumonitis [CB03] [60]
Givosiran DM5PFIJ Moderate Decreased metabolism of Zileuton caused by Givosiran mediated inhibition of CYP450 enzyme. Inborn porphyrin/heme metabolism error [5C58] [84]
Berotralstat DMWA2DZ Moderate Decreased metabolism of Zileuton caused by Berotralstat mediated inhibition of CYP450 enzyme. Innate/adaptive immunodeficiency [4A00] [85]
Ramelteon DM7IW9J Moderate Decreased metabolism of Zileuton caused by Ramelteon mediated inhibition of CYP450 enzyme. Insomnia [7A00-7A0Z] [86]
Tasimelteon DMLOQ1V Moderate Decreased metabolism of Zileuton caused by Tasimelteon mediated inhibition of CYP450 enzyme. Insomnia [7A00-7A0Z] [87]
Alosetron DML2A03 Moderate Decreased metabolism of Zileuton caused by Alosetron mediated inhibition of CYP450 enzyme. Irritable bowel syndrome [DD91] [88]
Brigatinib DM7W94S Moderate Increased metabolism of Zileuton caused by Brigatinib mediated induction of CYP450 enzyme. Lung cancer [2C25] [89]
PF-06463922 DMKM7EW Moderate Increased metabolism of Zileuton caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [90]
Osimertinib DMRJLAT Moderate Increased metabolism of Zileuton caused by Osimertinib mediated induction of CYP450 enzyme. Lung cancer [2C25] [91]
Capmatinib DMYCXKL Moderate Decreased metabolism of Zileuton caused by Capmatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [92]
Selpercatinib DMZR15V Moderate Decreased metabolism of Zileuton caused by Selpercatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [60]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Zileuton and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [93]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Zileuton and Idelalisib. Mature B-cell leukaemia [2A82] [94]
IPI-145 DMWA24P Moderate Decreased metabolism of Zileuton caused by IPI-145 mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [95]
Vemurafenib DM62UG5 Moderate Decreased metabolism of Zileuton caused by Vemurafenib mediated inhibition of CYP450 enzyme. Melanoma [2C30] [96]
Dabrafenib DMX6OE3 Moderate Increased metabolism of Zileuton caused by Dabrafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [60]
Exjade DMHPRWG Moderate Decreased metabolism of Zileuton caused by Exjade mediated inhibition of CYP450 enzyme. Mineral absorption/transport disorder [5C64] [97]
Fedratinib DM4ZBK6 Moderate Decreased metabolism of Zileuton caused by Fedratinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [60]
Nilotinib DM7HXWT Moderate Decreased metabolism of Zileuton caused by Nilotinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [98]
Olaparib DM8QB1D Moderate Increased metabolism of Zileuton caused by Olaparib mediated induction of CYP450 enzyme. Ovarian cancer [2C73] [70]
Rucaparib DM9PVX8 Moderate Decreased metabolism of Zileuton caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [99]
Rasagiline DM3WKQ4 Major Decreased metabolism of Zileuton caused by Rasagiline mediated inhibition of CYP450 enzyme. Parkinsonism [8A00] [70]
Abametapir DM2RX0I Moderate Decreased metabolism of Zileuton caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [100]
Lefamulin DME6G97 Moderate Decreased metabolism of Zileuton caused by Lefamulin mediated inhibition of CYP450 enzyme. Pneumonia [CA40] [101]
Lonafarnib DMGM2Z6 Moderate Decreased metabolism of Zileuton caused by Lonafarnib mediated inhibition of CYP450 enzyme. Premature ageing appearance [LD2B] [102]
Enzalutamide DMGL19D Moderate Increased metabolism of Zileuton caused by Enzalutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [103]
Temsirolimus DMS104F Moderate Increased plasma concentrations of Zileuton and Temsirolimus due to competitive inhibition of the same metabolic pathway. Renal cell carcinoma [2C90] [104]
Leflunomide DMR8ONJ Major Increased risk of hepatotoxicity by the combination of Zileuton and Leflunomide. Rheumatoid arthritis [FA20] [81]
Asenapine DMSQZE2 Moderate Decreased metabolism of Zileuton caused by Asenapine mediated inhibition of CYP450 enzyme. Schizophrenia [6A20] [105]
Pimozide DMW83TP Major Decreased metabolism of Zileuton caused by Pimozide mediated inhibition of CYP450 enzyme. Schizophrenia [6A20] [70]
Telotristat ethyl DMDIYFZ Moderate Increased metabolism of Zileuton caused by Telotristat ethyl mediated induction of CYP450 enzyme. Small intestine developmental anomaly [DA90] [60]
Larotrectinib DM26CQR Moderate Decreased metabolism of Zileuton caused by Larotrectinib mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [70]
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Zileuton and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [60]
Armodafinil DMGB035 Minor Increased metabolism of Zileuton caused by Armodafinil mediated induction of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [106]
LEE011 DMMX75K Moderate Decreased metabolism of Zileuton caused by LEE011 mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [107]
Fostamatinib DM6AUHV Moderate Decreased metabolism of Zileuton caused by Fostamatinib mediated inhibition of CYP450 enzyme. Thrombocytopenia [3B64] [108]
Sirolimus DMGW1ID Moderate Increased plasma concentrations of Zileuton and Sirolimus due to competitive inhibition of the same metabolic pathway. Transplant rejection [NE84] [104]
Tacrolimus DMZ7XNQ Moderate Increased plasma concentrations of Zileuton and Tacrolimus due to competitive inhibition of the same metabolic pathway. Transplant rejection [NE84] [104]
⏷ Show the Full List of 73 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Mannitol E00103 6251 Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Crospovidone E00626 Not Available Disintegrant
Eisenoxyd E00585 56841934 Colorant
Ferric hydroxide oxide yellow E00539 23320441 Colorant
Glyceryl dibehenate E00537 22477175 Binding agent; Coating agent; Flavoring agent; Modified-release agent; Viscosity-controlling agent; lubricant
Magnesium stearate E00208 11177 lubricant
Polyethylene glycol 400 E00653 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
⏷ Show the Full List of 13 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Zileuton 600 mg tablet 600 mg 12 HR Extended Release Oral Tablet Oral
Zileuton 600 mg tablet 600 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

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64 Product Information. Synercid (dalfopristin-quinupristin) Rhone-Poulenc Rorer, Collegeville, PA.
65 Product Information. Ketek (telithromycin). Aventis Pharmaceuticals, Bridgewater, NJ.
66 Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
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85 Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC.
86 Product Information. Rozerem (ramelteon). Takeda Pharmaceuticals America, Lincolnshire, IL.
87 Product Information. Hetlioz (tasimelteon). Vanda Pharmaceuticals Inc, Rockville, MD.
88 Product Information. Lotronex (alosetron). Glaxo Wellcome, Research Triangle Park, NC.
89 Product Information. Alunbrig (brigatinib). Ariad Pharmaceuticals Inc, Cambridge, MA.
90 Product Information. Lorbrena (lorlatinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
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96 Product Information. Zelboraf (vemurafenib). Genentech, South San Francisco, CA.
97 Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
98 Product Information. Tasigna (nilotinib). Novartis Pharmaceuticals, East Hanover, NJ.
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101 Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
102 Product Information. Zokinvy (lonafarnib). Eiger BioPharmaceuticals, Palo Alto, CA.
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