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
SMILES / InChI / InChIKey
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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)
InChI Key MWLSOWXNZPKENC-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1996))
IUPAC Name Click here for help
1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
International Nonproprietary Names Click here for help
INN number INN
6595 zileuton
Synonyms Click here for help
A-64077 | ZYFLO®
Database Links Click here for help
CAS Registry No. 111406-87-2
ChEBI CHEBI:10112
ChEMBL Ligand CHEMBL93
DrugBank Ligand DB00744
DrugCentral Ligand 2862
GtoPdb PubChem SID 178101979
PubChem CID 60490
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Tocris
Zileuton
Cat. No. 3308