Zileuton

Zileuton
Clinical data
Pronunciation	/zaɪˈluːtən/; zy-LOO-tən
Trade names	Zyflo
AHFS/Drugs.com	Monograph
MedlinePlus	a697013
License data	US DailyMed: Zileuton; US FDA: Zileuton;
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	Not yet established
Protein binding	93%
Metabolism	Hepatic (CYP1A2, CYP2C9 and CYP3A4-mediated)
Elimination half-life	2.5 hours
Excretion	Renal
Identifiers
	IUPAC name N-[1-(1-benzothien-2-yl)ethyl]-N-hydroxyurea;
CAS Number	111406-87-2 ;
PubChem CID	60490;
IUPHAR/BPS	5297;
DrugBank	DB00744 ;
ChemSpider	54531 ;
UNII	V1L22WVE2S;
KEGG	D00414 ;
ChEBI	CHEBI:10112 ;
ChEMBL	ChEMBL93 ;
CompTox Dashboard (EPA)	DTXSID9023752 ;
ECHA InfoCard	100.121.111
Chemical and physical data
Formula	C11H12N2O2S
Molar mass	236.29 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES O=C(N)N(O)C(c2sc1ccccc1c2)C;
	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) ; Key:MWLSOWXNZPKENC-UHFFFAOYSA-N ;
	(verify)

Zileuton (trade name Zyflo) is an orally active inhibitor of 5-lipoxygenase, and thus inhibits leukotrienes (LTB₄, LTC₄, LTD₄, and LTE₄) formation, used for the maintenance treatment of asthma. Zileuton was introduced in 1996 by Abbott Laboratories and is now marketed in two formulations by Cornerstone Therapeutics Inc. under the brand names Zyflo and Zyflo CR. The original immediate-release formulation, Zyflo, is taken four times per day. The extended-release formulation, Zyflo CR, is taken twice daily.

Although the 600 mg immediate release tablet (Zyflo) and extended release formulation of zileuton are still available (Zyflo CR), the 300 mg immediate release tablet was withdrawn from the U.S. market on February 12, 2008.

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