zileuton   Click here for help

GtoPdb Ligand ID: 5297

Synonyms: A-64077 | ZYFLO®
Approved drug Immunopharmacology Ligand
zileuton is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: 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 [2].
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: zileuton

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 94.8
Molecular weight 236.06
XLogP 0.92
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES ON(C(c1cc2c(s1)cccc2)C)C(=O)N
Isomeric SMILES ON(C(c1cc2c(s1)cccc2)C)C(=O)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)
No information available.
Summary of Clinical Use Click here for help
Used in the prophylaxis and chronic treatment of asthma.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Through its inhibition of 5-lipoxygenase, zileuton inhibits the formation of leukotrienes LTB4, LTC4, LTD4, and LTE4, which are formed from arachidonic acid in the reaction catalysed by this enzyme. An additional activity of zileuton is direct reduction of sebaceous lipids production [5].
Pharmacokinetics Click here for help
Organ function impairment
Zileuton should not be prescribed for patients with liver function impairment as it causes side effects including liver enzyme elevation.
External links Click here for help