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].
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2D Structure
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Physico-chemical Properties
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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
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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)
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-LOX Primary target of this compound Hs Inhibitor Inhibition 5.8 – 6.5 pIC50 - 1,3-4
pIC50 6.5 (IC50 3x10-7 M) [3]
Description: Inhibition of recombinant 5-LOX in vitro.
pIC50 6.4 (IC50 4x10-7 M) [1]
Description: Inhibition of leukotriene B4 biosynthesis by human polymorphonuclear leukocytes.
pIC50 5.8 (IC50 1.5x10-6 M) [4]
Description: Inhibition of purified recombinant human 5-LOX in a cell-free assay.
Ligand mentioned in the following text fields