Description References
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Zileuton

Description References
Product Name
Zileuton
CAS No.
111406-87-2
Chemical Name
Zileuton
Synonyms
ZYFLO;Zyfl;Leutml;ABT-077;Leutrol; A-64077;ZILEUTON;CGS-23622;Griluto-CR;AKOS 91253
CBNumber
CB1344903
Molecular Formula
C11H12N2O2S
Formula Weight
236.29
MOL File
111406-87-2.mol
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Zileuton Property

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)
pka
pKa 10.3(H2O t undefined I undefined) (Uncertain)
form 
powder
color 
white to off-white
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
CAS DataBase Reference
111406-87-2(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36
Safety Statements 
26
WGK Germany 
1
HS Code 
2934990002
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Z4277
Product name
Zileuton
Purity
≥98% (HPLC)
Packaging
10mg
Price
$84.1
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR2555
Product name
Zileuton
Packaging
200MG
Price
$186
Updated
2024/03/01
Sigma-Aldrich
Product number
1724656
Product name
Zileuton
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
150mg
Price
$436
Updated
2024/03/01
Cayman Chemical
Product number
10006967
Product name
Zileuton
Purity
>98%
Packaging
5mg
Price
$21
Updated
2024/03/01
Cayman Chemical
Product number
10006967
Product name
Zileuton
Purity
>98%
Packaging
10mg
Price
$38
Updated
2024/03/01
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Zileuton Chemical Properties,Usage,Production

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.

References

[1] A Rossi, C Pergola, A Koeberle, M Hoffmann, F Dehm, P Bramanti, S Cuzzocrea, O Werz and L Sautebin, The 5-lipoxygenase inhibitor, zileuton, suppresses prostaglandin biosynthesis by inhibition of arachidonic acid release in macrophages, British Journal of Pharmacology, 2010, col. 161, 555-570
[2] SE Wenzel and AK Kamada, Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma, Ann Pharmacother., 1996, vol. 30, 858-864

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.

Description

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%.

Chemical Properties

Crystalline Solid

Originator

Abbott (US)

Uses

An inhibitor of 5-lipoxygenase, the initial enzyme in the biosynthesis of leukotrienes from Arachidonic Acid. Used as an antiasthmatic.

Uses

gastric acid secretion inhibitor

Definition

ChEBI: A member of the class of 1-benzothiophenes that is 1-benzothiophene in which the hydrogen at position 2 is replaced by a 1-[carbamoyl(hydroxy)amino]ethyl group. A selective 5-lipoxygenase inhibitor, it inhibits the formation of leukotrienes LTB4, LTC4, LDT , and LTE4. It is used for the management of chronic asthma.

Manufacturing Process

N-Hydroxy-N-(1-benzo[b]thien-2-ylethyl) acetamide
1. 2-Acetyl benzo[b]thiophene.
Method a. Benzo[b]thiophene (10 g, 75 mmole) was dissolved in THF (50 ml) and cooled to -78°C. n-Butyl lithium (28 ml, 2.7 M in hexanes) was added. The mixture was stirred for 15 minutes and N,O-dimethyl acetohydroxamic acid was added. Following an additional 30 minutes of stirring, the reaction was quenched at -78°C with ethanol and 2 N HCl solution and extracted into ether. The solvent was removed in vacuo and the residue chromatographed on silica gel eluting with 20% ether in pentane to yield 6.9 g of the desired product as a white solid.
Method b. To a solution of benzo[b]thiophene (10.0 g, 75 mmole) in THF (50 ml) was added n-butyl lithium (33 ml, 2.5 M in hexanes) at -70°C under N 2 . The mixture, containing a white precipitate, was stirred at 70°C for 1 hour. Acetaldehyde (4.6 ml, 82 mmole) was added dropwise. After a few minutes the reaction was quenched with saturated NH 4 Cl solution. The layers were separated, the organic layer dried over MgSO4, filtered, and evaporated to give a white solid (10 g) which was used directly for the next step.
The alcohol prepared as described above (1.0 g) in acetone (50 ml) was cooled to 5°C and Jones Reagent was added dropwise until the orange yellow color persisted (1.4 ml). The reaction mixture was diluted with water and the desired product precipitated. It was collected by filtration to give 0.85 g.
2. 2-Acetyl benzo[b]thiophene oxime.
2-Acetyl benzo[b]thiophene (5 g, 28.4 mmole), prepared as described in step 1 above, and hydroxylamine hydrochloride (3.0 g, 42.6 mmole) were dissolved in a mixture of ethanol (50 ml) and pyridine (50 ml) and allowed to stir at room temperature for 2 hours. Most of the solvent was removed in vacuo and the residue dissolved in ether. After washing with 2 N HCl (100 ml), the solution was dried over MgSO 4 and evaporated. A white crystalline solid was obtained and was carried on without further purification. An alternative work-up may also be used. The reaction mixture was diluted with water (300 ml) and the product precipitated. It was filtered off and dried in vacuo.
3. 1-Benzo[b]thien-2-ylethyl hydroxylamine. The oxime prepared as in step 2 above (3.5 g, 18.5 mmole) was dissolved in ethanol (25 ml) and cooled to 0°C. Borane pyridine complex (3.7 ml, 37 mmole) was added via syringe under nitrogen followed 10 minutes later by 20% HCl in ethanol (30 ml). Within 30 minutes the reaction was complete and was brought to pH 9 with the addition of solid sodium carbonate or 2 N NaOH. The mixture was extracted into ether and dried over MgSO 4 . After evaporation a white solid (3.0 g) was obtained. This was carried on without further purification.
N-Hydroxy-N-(1-benzo[b]thien-2-ylethyl)urea
Method A. 1-Benzo[b]thien-2-yl ethyl hydroxyl amine prepared as described above, step 3 (2.0 g, 10 mmole), was refluxed for 30 minutes with trimethylsilyl isocyanate (1.65, 14.2 mmole) in dioxane (30 ml). The reaction mixture was then washed with saturated NH 4 Cl solution, dried with MgSO 4 , and evaporated.
Method B. 1-Benzo[b]thien-2-yl ethyl hydroxyl amine prepared as described in step 3, was dissolved in toluene (100 ml) and HCl gas was bubbled through the mixture at a moderate rate for about 4 minutes. The solution was then heated to reflux and phosgene was bubbled through for another 4 minutes. After an additional one hour reflux, the mixture was allowed to cool to room temperature and then added to excess cold ammonium hydroxide solution. The precipitate was collected and recrystallized. Melting point: 157°-158°C. NMR (300 MHz), and mass spectrum confirmed the structure of the prepared compound.

brand name

Zyflo (Sensus).

Therapeutic Function

Antiallergic, Antiinflammatory

Biological Activity

Orally active 5-lipoxygenase (5-LOX) inhibitor that inhibits LTB 4 synthesis (IC 50 values are 0.56, 2.3 and 2.6 μ M in dog, rat and human blood respectively). Inhibits antigen-induced contraction of tracheal strips in vitro (IC 50 = 6 μ M) and exhibits antiasthmatic activity in vivo . Also weakly inhibits CYP1A2 (K i = 66 - 98 μ M).

Biochem/physiol Actions

Zileuton is an anti-asthmatic, an inhibitor of 5-lipoxygenase; the initial enzyme in the biosynthesis of leukotrienes from arachidonic acid.

storage

Store at +4°C

References

1) Carter et al. (1991), 5-Lipoxygense inhibitory activity of zileuton; J. Pharmacol. Exp. Ther. 256 929 2) Rossi et al. (2010), The 5-lipoxygenase inhibitor, zileuton, suppresses prostaglandin biosynthesis by inhibition of arachidonic acid release in macrophages; Br. J. Pharmacol. 161 555

Zileuton Preparation Products And Raw materials

Raw materials

2-Acetylbenzo[b]thiophene Borane 1,4-Dioxane Potassium cyanate weak Alkyl isocyanate Hydroxylamine hydrochloride

Preparation Products

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View Lastest Price from Zileuton manufacturers

Qiuxian Baitai New Material Co., LTD
Product
Zileuton 111406-87-2
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
200000pcs
Release date
2021-03-16
Zhuozhou Wenxi import and Export Co., Ltd
Product
Zileuton 111406-87-2
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-08-11
Zhuozhou Wenxi import and Export Co., Ltd
Product
Zileuton 111406-87-2
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10

111406-87-2, ZileutonRelated Search:

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