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

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: zileuton

zileuton is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
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)
InChI Key MWLSOWXNZPKENC-UHFFFAOYSA-N
References
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]