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)
1. Carter GW, Young PR, Albert DH, Bouska J, Dyer R, Bell RL, Summers JB, Brooks DW. (1991)
5-lipoxygenase inhibitory activity of zileuton.
J Pharmacol Exp Ther, 256 (3): 929-37. [PMID:1848634]
2. Malec J, Przybyszewski WM, Grabarczyk M, Sitarska E. (1984)
Hydroxyurea has the capacity to induce damage to human erythrocytes which can be modified by radical scavengers.
Biochem Biophys Res Commun, 120 (2): 566-73. [PMID:6732772]
3. Prasher P, Pooja, Singh P. (2014)
Lead modification: amino acid appended indoles as highly effective 5-LOX inhibitors.
Bioorg Med Chem, 22 (5): 1642-8. [PMID:24508141]
4. Sinha S, Doble M, Manju SL. (2018)
Design, synthesis and identification of novel substituted 2-amino thiazole analogues as potential anti-inflammatory agents targeting 5-lipoxygenase.
Eur J Med Chem, 158: 34-50. [PMID:30199704]
5. Zouboulis ChC, Saborowski A, Boschnakow A. (2005)
Zileuton, an oral 5-lipoxygenase inhibitor, directly reduces sebum production.
Dermatology (Basel), 210 (1): 36-8. [PMID:15604543]