General
Preferred name
ZILEUTON
Synonyms
Abbott-64077 ()
Abbott 64077 ()
A 64077 ()
Zileuton (sodium) ()
ZILEUTON111406-87-2 ()
A 64077 (sodium) ()
Abbott 64077 (sodium) ()
Zileuton (A-64077) ()
A-64077, Abbott 64077, ZYFLO ()
Zileuton sodium ()
Zyflo Cr ()
ZYFLO ()
NSC-730712 ()
NSC-759277 ()
ABBOTT-64077 ()
A-64077 ()
Zileuton-d4 ()
P&D ID
PD000269
CAS
111406-87-2
118569-21-4
1189878-76-9
Tags
natural product
drug
available
Approved by
FDA
First approval
1996
Drug Status
investigational
approved
withdrawn
Drug indication
Inhibitor (5-lipoxygenase)
Asthma
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ROE
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.
TOXICITY
Minimum oral lethal dose of zileuton in various preparations was 500-4000 mg/kg in mice and 300-1000 mg/kg in rats (providing greater than 3 and 9 times the systemic exposure [AUC] achieved at the maximum recommended human daily oral dose, respectively).
DESCRIPTION
Zileuton is an orally active 5-LOX inhibitor.
The approved drug is a racemic mixture of R(+) and S(-) enantiomers (PubChem CID 10681296 and CID 10220327 respectively), which are both pharmacologically active. The structure shown here does not specify stereochemistry and represents the mixture.
The approved drug is a racemic mixture of R(+) and S(-) enantiomers (PubChem CID 10681296 and CID 10220327 respectively), which are both pharmacologically active. The structure shown here does not specify stereochemistry and represents the mixture.
DESCRIPTION
Zileuton is an orally active 5-LOX inhibitor.
The approved drug is a racemic mixture of R(+) and S(-) enantiomers (PubChem CID 10681296 and CID 10220327 respectively), which are both pharmacologically active. The structure shown here does not specify stereochemistry and represents the mixture.
The hepatotoxicity of zileuton is suggested to be due to the N-hydroxyurea group . (GtoPdb)
The approved drug is a racemic mixture of R(+) and S(-) enantiomers (PubChem CID 10681296 and CID 10220327 respectively), which are both pharmacologically active. The structure shown here does not specify stereochemistry and represents the mixture.
The hepatotoxicity of zileuton is suggested to be due to the N-hydroxyurea group . (GtoPdb)
DESCRIPTION
Potent HMG-CoA reductase inhibitor
(Tocris Bioactive Compound Library)
DESCRIPTION
Orally active 5-LOX inhibitor
(Tocriscreen Plus)
DESCRIPTION
Zileuton sodium is an inhibitor of 5-lipoxygenase, and thus inhibits leukotrienes(LTB4, LTC4, LTD4 and LTE4) formation with an IC50 value of 0.5μM.
Zileuton sodium has been reported to concentration-dependently inhibit the 5-lipoxygenase activity with an IC50 value of 0.5μM in RBL-1cell lysate. In addition, Zileuton sodium has been found to be a potent inhibitor of LTB formation with an IC50 value of 0.6μM. Furthermore, stimulated with A23187, Zileuton sodium has shown a dose-dependent reduction in LTB4 and 5-HETE generation in rat leukocyte with IC50 values of 0.38μM and 0.31μM, respectively. About 40-fold higher concentrations of Zileuton sodium also reduced the production of PGE2 with a IC50 of 16μM. (BOC Sciences Bioactive Compounds)
Zileuton sodium has been reported to concentration-dependently inhibit the 5-lipoxygenase activity with an IC50 value of 0.5μM in RBL-1cell lysate. In addition, Zileuton sodium has been found to be a potent inhibitor of LTB formation with an IC50 value of 0.6μM. Furthermore, stimulated with A23187, Zileuton sodium has shown a dose-dependent reduction in LTB4 and 5-HETE generation in rat leukocyte with IC50 values of 0.38μM and 0.31μM, respectively. About 40-fold higher concentrations of Zileuton sodium also reduced the production of PGE2 with a IC50 of 16μM. (BOC Sciences Bioactive Compounds)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
2
Organisms
3
Compound Sets
33
Axon Medchem Screening Library
BOC Sciences Bioactive Compounds
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
NCATS Inxight Approved Drugs
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
The Spectrum Collection
Tocris Bioactive Compound Library
Tocriscreen Plus
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
46
Molecular Weight
236.06
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
2
Rotatable Bonds
2
Ring Count
2
Aromatic Ring Count
2
cLogP
2.73
TPSA
66.56
Fraction CSP3
0.18
Chiral centers
1.0
Largest ring
6.0
QED
0.62
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target Type
Enzymes
Target
5-Lipoxygenase
Arachidonate 5-lipoxygenase
COX-1
5-LOX inhibitor
Ferroptosis
Lipoxygenase
Apoptosis related,Ferroptosis,Lipoxygenase
MOA
leukotriene synthase inhibitor
Inhibitor
5-Lipoxygenase inhibitor
5-Lipoxygenase Inhibitors
Leukotriene Synthesis Inhibitors
Pathway
Immunology/Inflammation
Metabolism
Neuroscience
Apoptosis
Metabolic Enzyme/Protease
Primary Target
Lipoxygenases
Member status
member
Therapeutic Class
Antiinflammatory Agents
Source data
