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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:31 UTC
HMDB IDHMDB0014882
Secondary Accession Numbers
  • HMDB14882
Metabolite Identification
Common NameZileuton
DescriptionLeukotrienes 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.
Structure
Data?1582753231
Synonyms
ValueSource
(+-)-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyureaChEBI
LeutrolChEBI
N-(1-Benzo(b)thien-2-ylethyl)-N-hydroxyureaChEBI
N-[1-(Benzo[b]thiophen-2-yl)ethyl]-N-hydroxyureaChEBI
ZileutonumChEBI
ZyfloChEBI
Abbot 64077HMDB
Chemical FormulaC11H12N2O2S
Average Molecular Weight236.29
Monoisotopic Molecular Weight236.061948328
IUPAC Name1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
Traditional Namezileuton
CAS Registry Number111406-87-2
SMILES
CC(N(O)C(N)=O)C1=CC2=CC=CC=C2S1
InChI Identifier
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)
InChI KeyMWLSOWXNZPKENC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiophenes
Sub Class1-benzothiophenes
Direct Parent1-benzothiophenes
Alternative Parents
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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point144.2 - 145.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.054 g/LNot Available
LogP0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.054 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.96 m³·mol⁻¹ChemAxon
Polarizability24.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-5900000000-908922c27d630436d92cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0890000000-11bd11a737d7518926f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p6-3950000000-6c73d72fe4a0c46d1d46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-3900000000-bbd6a4285b05c7584d16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-8950000000-009b3f6f4b890a437b14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-7920000000-b16eff6e7f5c11222359Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-ddee52c368588e30fb4aSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00744 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00744 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00744
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54531
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkZileuton
METLIN IDNot Available
PubChem Compound60490
PDB IDNot Available
ChEBI ID10112
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  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. 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 ]