Zileuton
Synonym(s):(±)-N-hydroxy-N-(1-benzo[b]thien-2-ylethyl)urea;Zileuton
- CAS NO.:111406-87-2
- Empirical Formula: C11H12N2O2S
- Molecular Weight: 236.29
- MDL number: MFCD00866097
- EINECS: 601-087-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-06-30 15:45:59
What is Zileuton?
Absorption
Rapidly and almost completely absorbed. The absolute bioavailability is unknown.
Toxicity
Minimum oral lethal dose of zileuton in various preparations was 500-4000 mg/kg in mice and 300-1000 mg/kg in rats (providing greater than 3 and 9 times the systemic exposure [AUC] achieved at the maximum recommended human daily oral dose, respectively).
Description
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.
The Uses of Zileuton
An inhibitor of 5-lipoxygenase, the initial enzyme in the biosynthesis of leukotrienes from Arachidonic Acid. Used as an antiasthmatic
Background
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 The immediate release tablet of Zileuton has been withdrawn from the US market.
Indications
For the prophylaxis and chronic treatment of asthma in adults and children 12 years of age and older.
What are the applications of Application
Zileuton is a 5-LO (5-lipoxygenase) inhibitor
Pharmacokinetics
Zileuton is an asthma drug that differs chemically and pharmacologically from other antiasthmatic agents. It blocks leukotriene synthesis by inhibiting 5-lipoxygenase, an enzyme of the eicosanoid synthesis pathway. Current data indicates that asthma is a chronic inflammatory disorder of the airways involving the production and activity of several endogenous inflammatory mediators, including leukotrienes. Sulfido-peptide leukotrienes (LTC4, LTD4, LTE4, also known as the slow-releasing substances of anaphylaxis) and LTB4, a chemoattractant for neutrophils and eosinophils, are derived from the initial unstable product of arachidonic acid metabolism, leukotriene A4 (LTA4), and can be measured in a number of biological fluids including bronchoalveolar lavage fluid (BALF) from asthmatic patients. In humans, pretreatment with zileuton attenuated bronchoconstriction caused by cold air challenge in patients with asthma.
Metabolism
Hepatic. Zileuton and its N-dehydroxylated metabolite are oxidatively metabolized by the cytochrome P450 isoenzymes 1A2, 2C9 and 3A4.
Properties of Zileuton
Melting point: | 157-158°C |
Boiling point: | 449.4±47.0 °C(Predicted) |
Density | 1.401±0.06 g/cm3(Predicted) |
storage temp. | room temp |
solubility | DMSO: ≥20mg/mL at ~60°C (warm up to 60 C for 5min) |
form | powder |
color | white to off-white |
Safety information for Zileuton
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 Health Hazard GHS08 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Precautionary Statement Codes |
P202:Do not handle until all safety precautions have been read and understood. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P308+P313:IF exposed or concerned: Get medical advice/attention. |
Computed Descriptors for Zileuton
Abamectin manufacturer
Solara Active Pharma Sciences Ltd
Biophore India Pharmaceuticals Pvt Ltd
Aspen Biopharma Labs Pvt Ltd
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