Leutml
Zileuton
CAS: 111406-87-2
Molecular Formula: C11H12N2O2S
Leutml - Names and Identifiers
| Name | Zileuton |
| Synonyms | Zyfl Leutml A-64077 Leutrol Zileuton Abbott 64077 Zileuton and its intermediates Urea, N-(1-benzo[b]thien-2-ylethyl)-N-hydroxy- 1-[1-(1-benzothiophén-2-yl)éthyl]-1-hydroxyurée 1-[1-(1-Benzothiophen-2-yl)ethyl]-1-hydroxyurea 1-(1-(BENZO[B]THIOPHEN-2-YL)ETHYL)-1-HYDROXYUREA 1-[1-(1-Benzothiophen-2-yl)ethyl]-1-hydroxyharnstoff |
| CAS | 111406-87-2 |
| EINECS | 601-087-3 |
| InChI | InChI=1/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) |
Leutml - Physico-chemical Properties
| Molecular Formula | C11H12N2O2S |
| Molar Mass | 236.29 |
| Density | 1.401±0.06 g/cm3(Predicted) |
| Melting Point | 157-158°C |
| Boling Point | 449.4±47.0 °C(Predicted) |
| Flash Point | 225.6°C |
| Solubility | DMSO: ≥20mg/mL at ~60°C (warm up to 60 C for 5min) |
| Vapor Presure | 7.29E-09mmHg at 25°C |
| Appearance | White to white-like powder |
| Color | white to off-white |
| pKa | pKa 10.3(H2Ot undefinedI undefined) (Uncertain) |
| Storage Condition | room temp |
| 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. |
| Refractive Index | 1.704 |
| MDL | MFCD00866097 |
| Physical and Chemical Properties | Crystallization, melting point 157~158 deg C. |
| Use | For the treatment of asthma medication |
Leutml - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R36 - Irritating to the eyes |
| Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 1 |
| HS Code | 2934990002 |
Leutml - Reference
| Reference Show more | 1. Yan, Wen-xia, et al. "Anti-inflammatory activity studies on the stems and roots of Jasminum lanceolarium Roxb." Journal of ethnopharmacology 171 (2015): 335-341.https://doi.org/10.1016/j.jep.2015.05.044 |
Leutml - Nature
Open Data Verified Data
Crystal, melting point 157~158 °c.
Last Update：2024-01-02 23:10:35
Leutml - Preparation Method
Open Data Verified Data
2-acetylbenzothiophene was dissolved in a solution of pyridine in ethanol (1:1), hydroxylamine hydrochloride was added and reacted at room temperature. Borane-pyridine complex was added to the ethanol solution of the reaction product, and then an ethanol solution of hydrogen chloride was added dropwise to reduce the reaction product to obtain hydroxylamine. Hydroxylamine Trimethylsilyl isocyanate is added to dioxane and heated to give zileuton, or the above hydroxylamine is reacted with potassium fluorate and hydrochloric acid aqueous solution to give zileuton.
Last Update：2022-01-01 09:23:06
Leutml - Use
Open Data Verified Data
developed by Abbott, USA, was launched in the United States in 1997. Anti-leukotriene drugs. By inhibition of 5-lipoxygenase, leukotriene production is reduced for the treatment of asthma.
Last Update：2022-01-01 09:23:07
Leutml - Reference Information
| anti-asthma drugs | asthma is a common chronic disease, with a prevalence rate of about 10% in developed countries, and its incidence and disability rate are increasing in the world. Asthma has attracted worldwide attention. In the late 1980s, asthma was considered to be a chronic inflammatory disease characterized by airway hyperresponsiveness and reversible airway obstruction. With the in-depth research on the mechanism of airway inflammation in asthma, the development of anti-inflammatory therapy, including specific mediator antagonists, has become a hot spot in the prevention and management of asthma. Among the current anti-asthma drugs, β2 agonists can quickly inhibit symptoms, but clinical application has found that agonists are related to increased asthma mortality, and rebound phenomenon occurs after stopping the drug and may aggravate asthma. Theophylline preparations have narrow therapeutic windows and large toxic and side effects. Corticosteroids are effective, but their anti-inflammatory effects are non-specific and have many adverse reactions. The treatment of asthma still needs to develop new effective and safe drugs. The research on lipid mediator antagonists and inhibitors of asthma is a new way to treat asthma. The pathological basis of asthma attack is airway inflammation, and leukotriene is an important mediator of airway allergic inflammation. Therefore, the successful research of leukotriene antagonist is a major breakthrough in asthma treatment in recent years. Ziluton (Zileuton) is a novel selective 5-lipoxygenase inhibitor that antagonizes leukotriene synthesis by inhibiting lipoxygenase. Leukotriene is a highly active inflammatory substance synthesized by tetraenoic acid through lipoxygenase pathway, which plays an important role in the pathogenesis of asthma. Its mechanism of action is to effectively control the development of asthma inflammation by inhibiting the synthesis of leukotrienes. As a new type of anti-asthma drug, Zilutong has certain tracheal protection, tracheal dilation and anti-inflammatory effects. In the United States, due to its positive efficacy and small side effects, it has been officially included in the National Asthma Education and Prevention Program in the United States as a therapeutic drug for long-term asthma control (currently included in the varieties of zafirlukast and ziluton). Ziluton's chemical name is N-hydroxy-N-[1-(2-benzothiophene) ethyl] urea. It was developed by Abbott in the United States and was approved by the FDA in 1997 for the prevention and treatment of chronic asthma over 12 years old. |
| use | is suitable for asthma, especially the spastic contraction of trachea and bronchus caused by antigen and aspirin, thus improving lung function. It can selectively inhibit the biosynthesis of 5-lipoxygenase for asthma. for the treatment of asthma |
| Synthesis route | Using 2-acetylbenzothiophene as the starting material, the target compound was synthesized by three steps of oximation, reduction and condensation. Liutong. Fig. 1 shows the synthesis route of zilyutong |
| adverse reactions | this product is well tolerated without serious adverse reactions. occasionally, serum liver enzyme increases and can be recovered after drug withdrawal. |
| precautions | before using this product, check liver function first, check once a month after starting medication, check once every 2~3 months after 3 months, and check regularly after 1 year. In addition, indigestion can be seen. The female mice were given 4 times the adult dose of Zilletong. After 2 years of medication, the incidence of liver, kidney and vascular tumors was found to increase. This product is metabolized by isomerase such as cytochrome P450 1A2, 2C9 and 3A4. When used with the following drugs, it can reduce the elimination of theophylline, significantly increase its serum concentration, and also significantly increase the blood concentration of warfarin (coumarin, etc.), propranoline, and terfenadine. (2016-01-30) |
| Production method | 2-acetylbenzo [B] thiophene (Ⅰ) is dissolved in pyridine-ethanol (1:1) solution, and hydroxylamine hydrochloride is added to react at room temperature. Then add the borane-pyridine complex to the produced oxime (II) ethanol solution, and then drop the ethanol solution 20% hydrogen chloride to reduce to obtain hydroxylamine (III). (Ⅲ) Add trimethylsilyl isocyanate to dioxane and heat to obtain the product;(Ⅲ) Or react with potassium cyanate and hydrochloric acid aqueous solution to obtain the product. |
Last Update：2024-04-09 21:04:16
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Multiple SpecificationsSpot supply
Product Name: Zileuton Visit Supplier Webpage Request for quotationCAS: 111406-87-2
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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