Chemical Property of Zileuton
Chemical Property:
- Appearance/Colour:crystalline solid
- Vapor Pressure:7.29E-09mmHg at 25°C
- Melting Point:157-158 °C
- Refractive Index:1.704
- Boiling Point:449.4 °C at 760 mmHg
- PKA:pKa 10.3(H2O
t undefined
I undefined) (Uncertain)
- Flash Point:225.6 °C
- PSA：94.80000
- Density:1.401 g/cm3
- LogP:3.43250
- Storage Temp.:Store at +4°C
- Solubility.:DMSO: ≥20mg/mL at ~60°C (warm up to 60 C for 5min)
- XLogP3:1.6
- Hydrogen Bond Donor Count:2
- Hydrogen Bond Acceptor Count:3
- Rotatable Bond Count:2
- Exact Mass:236.06194880
- Heavy Atom Count:16
- Complexity:275
- Purity/Quality:
-
99% *data from raw suppliers
Zileuton *data from reagent suppliers
Safty Information:
- Pictogram(s):
Xn
- Hazard Codes:Xn
- Statements:
22-36
- Safety Statements:
26
- MSDS Files:
-
SDS file from LookChem
Useful:
- Drug Classes:Antiasthmatic Agents
- Canonical SMILES:CC(C1=CC2=CC=CC=C2S1)N(C(=O)N)O
- Recent ClinicalTrials:Aspirin and Zileuton and Biomarker Expression in Nasal Tissue of Current Smokers
- Recent EU Clinical Trials:Application of zileuton (Zyflo CR) in patients with Sj?gren Larsson Syndrome
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Description
Zileuton, a benzothiophene N-hydroxyurea, is the only approved inhibitor of 5-lipoxygenase. It is believed to intervene with allergic and inflammatory diseases by suppression of leukotriene (LT) biosynthesis. The compound belongs to the class of iron ligand-type inhibitors of 5-lipoxygenase that not only chelates the active site iron of the enzyme but also possesses weak-reducing properties.
Zileuton is used as a type of drug for the prophylaxis and chronic treatment of asthma. Zileuton is a reversible 5-lipoxygenase (5-LO) inhibitor. It inhibits 5-LO activity in rat basophilic leukemia-1 (RBL-1) cell supernatant with an IC50 value of 0.5 μM. Zileuton inhibits leukotriene B4 (LTB4; ) production induced by the calcium ionophore A23187 in purified human peripheral blood polymorphonuclear leukocytes (PMNLs; IC50 = 0.6 μM). Zileuton (10 mg/kg, p.o.) prevents antigen challenge-induced increases in specific lung resistance in a sheep model of asthma at 4 to 8 hours post-challenge following administration 2 hours pre-challenge. Formulations containing zileuton have been used in the prophylaxis and chronic treatment of asthma. Zyflo was launched in the US for chronic asthma. It can be prepared in three
steps from 2-acetylbenzo[b]thiophene. Zyflo is a reversible direct inhibitor of 5-
lipoxgenase that is orally-active. It was able to effect a 70-100 YO reduction in LTB4,
LTE4, LTD4 and LTC4. Zyflo has no effect on myeloperoxidase activity, neutrophil
degranulation, mast cell histamine release or phospholipase A2 activities. It did not
inhibit cyclooxygenase as witnessed by the formation of TXB2. It significantly
attentuated asthmatic response to cold dry air, inhibited exercise-induce
bronchoconstriction, and attenuated induced bronchospasms. Zyflo has
antiinflammatory effects as witnessed by a decrease in edema, mucus production and
cellular infiltration. It had a bronchodilatory effect within 2 h and increased spirometry
results by 18%.
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Uses
An inhibitor of 5-lipoxygenase, the initial enzyme in the biosynthesis of leukotrienes from Arachidonic Acid. Used as an antiasthmatic gastric acid secretion inhibitor An inhibitor of 5-lipoxygenase, the initial enzyme in the biosynthesis of leukotrienes from Arachidonic Acid. Used as an antiasthmatic.
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Therapeutic Function
Antiallergic, Antiinflammatory
