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Namespace Prefixes

PrefixIRI
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n16http://linked.opendata.cz/resource/drugbank/drug/DB00744/identifier/chebi/

Statements

Subject Item
n2:DB00744
rdf:type
n3:Drug
n3:description
Leukotrienes are substances that induce numerous biological effects including augmentation of neutrophil and eosinophil migration, neutrophil and monocyte aggregation, leukocyte adhesion, increased capillary permeability, and smooth muscle contraction. These effects contribute to inflammation, edema, mucus secretion, and bronchoconstriction in the airways of asthmatic patients. Zileuton relieves such symptoms through its selective inhibition of 5-lipoxygenase, the enzyme that catalyzes the formation of leukotrienes from arachidonic acid. Specifically, it inhibits leukotriene LTB4, LTC4, LTD4, and LTE4 formation. Both the R(+) and S(-) enantiomers are pharmacologically active as 5-lipoxygenase inhibitors in in vitro systems. The immediate release tablet of Zileuton has been withdrawn from the US market.
n3:dosage
n23:271B55CD-363D-11E5-9242-09173F13E4C5 n23:271B55CE-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Berger W, De Chandt MT, Cairns CB: Zileuton: clinical implications of 5-Lipoxygenase inhibition in severe airway disease. Int J Clin Pract. 2007 Apr;61(4):663-76. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17394438 # Wenzel SE, Kamada AK: Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma. Ann Pharmacother. 1996 Jul-Aug;30(7-8):858-64. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8826571 # Malo PE, Bell RL, Shaughnessy TK, Summers JB, Brooks DW, Carter GW: The 5-lipoxygenase inhibitory activity of zileuton in in vitro and in vivo models of antigen-induced airway anaphylaxis. Pulm Pharmacol. 1994 Apr;7(2):73-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8081074
n3:group
approved investigational withdrawn
n3:halfLife
2.5 hours
n3:indication
For the prophylaxis and chronic treatment of asthma in adults and children 12 years of age and older.
n3:manufacturer
n12:271B55C8-363D-11E5-9242-09173F13E4C5
owl:sameAs
n11:DB00744 n24:DB00744
dcterms:title
Zileuton
adms:identifier
n9:46506394 n14:54531 n15:DB00744 n16:10112 n17:PA451955 n18:60490 n19:D00414 n20:68734-700-10 n27:Zileuton
n3:mechanismOfAction
Leukotrienes are substances that induce numerous biological effects including augmentation of neutrophil and eosinophil migration, neutrophil and monocyte aggregation, leukocyte adhesion, increased capillary permeability, and smooth muscle contraction. These effects contribute to inflammation, edema, mucus secretion, and bronchoconstriction in the airways of asthmatic patients. Zileuton relieves such symptoms through its selective inhibition of 5-lipoxygenase, the enzyme that catalyzes the formation of leukotrienes from arachidonic acid. Specifically, it inhibits leukotriene LTB4, LTC4, LTD4, and LTE4 formation. Both the R(+) and S(-) enantiomers are pharmacologically active as 5-lipoxygenase inhibitors in <i>in vitro</i> systems. Due to the role of leukotrienes in the pathogenesis of asthma, modulation of leukotriene formation by interruption of 5-lipoxygenase activity may reduce airway symptoms, decrease bronchial smooth muscle tone, and improve asthma control.
n3:packager
n12:271B55C5-363D-11E5-9242-09173F13E4C5 n12:271B55C6-363D-11E5-9242-09173F13E4C5 n12:271B55C3-363D-11E5-9242-09173F13E4C5 n12:271B55C4-363D-11E5-9242-09173F13E4C5 n12:271B55C7-363D-11E5-9242-09173F13E4C5
n3:patent
n7:5422123 n7:4873259
n3:routeOfElimination
Elimination of zileuton is predominantly via metabolism with a mean terminal half-life of 2.5 hours. The urinary excretion of the inactive N-dehydroxylated metabolite and unchanged zileuton each accounted for less than 0.5% of the dose.
n3:synonym
(+-)-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea Zyflo Zileutonum Zileuton N-(1-Benzo(b)thien-2-ylethyl)-N-hydroxyurea Leutrol N-[1-(Benzo[b]thiophen-2-yl)ethyl]-N-hydroxyurea
n3:toxicity
The oral minimum lethal doses in mice and rats were 500-4000 and 300-1000 mg/kg in various preparations, respectively (providing greater than 3 and 9 times the systemic exposure [AUC] achieved at the maximum recommended human daily oral dose, respectively).
n3:volumeOfDistribution
* 1.2 L/kg
n3:proteinBinding
93% bound to plasma proteins, primarily to albumin.
n3:synthesisReference
Emanuele ATTOLINA, Gianmaria Dell'Anna, Roberto Rossi, Pietro Allegrini, Gabriele Razzetti, "PROCESS FOR THE PREPARATION OF ZILEUTON." U.S. Patent US20090286996, issued November 19, 2009.
n21:hasConcept
n22:M0175142
foaf:page
n6:zileuton.htm n25:zileuton.html
n3:IUPAC-Name
n4:271B55D3-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B55D9-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B55D8-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B55D5-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B55D6-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B55D7-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B55D1-363D-11E5-9242-09173F13E4C5 n4:271B55E9-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B55D2-363D-11E5-9242-09173F13E4C5 n4:271B55CF-363D-11E5-9242-09173F13E4C5 n4:271B55EB-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B55D0-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count
n4:271B55DF-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B55E0-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B55DA-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B55DB-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B55DD-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B55DC-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B55DE-363D-11E5-9242-09173F13E4C5
n3:absorption
Rapidly and almost completely absorbed. The absolute bioavailability is unknown.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
111406-87-2
n3:category
n3:clearance
* Apparent oral cl=7 mL/min/kg
n3:containedIn
n13:271B55C9-363D-11E5-9242-09173F13E4C5 n13:271B55CC-363D-11E5-9242-09173F13E4C5 n13:271B55CA-363D-11E5-9242-09173F13E4C5 n13:271B55CB-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B55E5-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B55E7-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B55E8-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B55EA-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B55E4-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B55E3-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B55E6-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B55D4-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B55E1-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B55E2-363D-11E5-9242-09173F13E4C5