2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino] ethyl]-phenol
Salmeterol
CAS: 89365-50-4
Molecular Formula: C25H37NO4
2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino] ethyl]-phenol - Names and Identifiers
| Name | Salmeterol |
| Synonyms | gr33343x SAMETEROL Salmeterol SALMETEROL SALMETEROL(SUBJECTTOPATENTFREE) 4-HYDROXY-A1-[[[6-(4-PHENYLBUTOXY)HEXYL]AMINO]METHYL]-1,3-BENZENEDIMETHANOL (+-)-4-hydroxy-alpha1-(((6-(4-phenylbutoxy)hexyl)amino)methyl)-1,3-benzenedi 2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino] ethyl]-phenol 1,3-benzenedimethanol,4-hydroxy-alpha1-(((6-(4-phenylbutoxy)hexyl)amino)methyl |
| CAS | 89365-50-4 |
| InChI | InChI=1/C25H37NO4/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2 |
2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino] ethyl]-phenol - Physico-chemical Properties
| Molecular Formula | C25H37NO4 |
| Molar Mass | 415.57 |
| Density | 1.112±0.06 g/cm3(Predicted) |
| Melting Point | 75.5-76.5° |
| Boling Point | 603.0±55.0 °C(Predicted) |
| Solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
| Appearance | Solid |
| Color | White to Off-White |
| pKa | 9.99±0.31(Predicted) |
| Storage Condition | 2-8°C |
| Use | For long-term prevention and treatment of asthma, chronic bronchitis, emphysema with reversible airway obstruction. |
2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino] ethyl]-phenol - Risk and Safety
| RTECS | CZ6457000 |
2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino] ethyl]-phenol - Nature
Open Data Verified Data
melting point 75. 5-76.5 °c. Soluble in methanol, ethanol-soluble, chloroform or isopropanol, insoluble in water.
Last Update：2024-01-02 23:10:35
2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino] ethyl]-phenol - Preparation Method
Open Data Verified Data
4-phenylbutanol, 1,6-= bromohexane, tetrabutylammonium bisulfate and 50% aqueous sodium hydroxide solution, heated at 65-70 °c for 4H, the resulting compound is condensed with 3-hydroxymethyl -4,a-dihydroxyphenylethylamine to give salmeterol.
Last Update：2022-01-01 09:09:58
2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino] ethyl]-phenol - Use
Open Data Verified Data
Glaxo, UK, was launched in 1990. A novel selective long-acting p2-receptor agonist produces significant Tracheal dilation. Inhibiting the release of allergic reaction mediators by pulmonary mast cells can inhibit the early and late phase reactions induced by inhaled antigen and reduce airway hyperresponsiveness. For the long-term routine treatment of asthma with reversible respiratory obstruction and chronic bronchitis.
Last Update：2022-01-01 09:09:59
2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino] ethyl]-phenol - Reference Information
| asthma medication | salmeterol is an asthma medication developed from the molecular structure of salbutamol, just one more tail part, which is tightly bound to the specific structure next to the beta 2 receptor, the extra-receptor site, which allows the other parts of the molecule to act freely on the beta 2 receptor, and for this reason, so that the product can continue to stay in the role of the position. salmeterol can be used as a long-acting β2-agonist in bronchodilators for the daily management of asthma symptoms. It can be used for the long-term treatment of reversible airway obstruction in asthma (including nocturnal asthma and exercise-induced asthma), chronic bronchitis and emphysema, and is not suitable for acute asthma attacks. |
| Antiasthmatic drugs | Antiasthmatic drugs are drugs that can act on different links of asthma attack to relieve or prevent bronchial asthma attack. Salmeterol is a new type of selective long-acting β2 receptor agonist antiasthmatic drug, which is derived from salbutamol and binds more closely to β2 receptor, resulting in a more lasting agonistic effect. The chemical name of hydroxynaphthoate, white or white powder, taste slightly bitter, by the British GlaxoSmithKline company for the first time successfully developed in 1990 in the United Kingdom, the earliest listing, trade name known as Shi Libiao, si Domi, hirudo and sermitro have strong inhibitory effect on the release of allergic reaction mediators from pulmonary mast cells, which can inhibit the early and late phase reaction induced by inhaled antigen and reduce tracheal hyperreactivity. Clinical trials have shown that salmeterol is more potent than salbutamol, producing a longer duration of protection against asthma caused by histamine-induced bronchoconstriction and exercise, with a longer duration of action, a smaller extrapulmonary effect, it is well tolerated and is currently the ideal drug for the treatment of nocturnal asthma attacks and asthma maintenance therapy. pharmacokinetic study showed that this product was 50 μg twice a day, and the maximum plasma concentration was 5-15 min after one inhalation of 50 and 400 μg, 0.1~0.2 μg/L and 1 ~ μg/L, respectively. This product is strongly metabolized by hydrolysis, and most of the dose is eliminated within 72H. 23% and 57% of the dose was found in urine and feces respectively within H. In addition, salmeterol has a control effect on inflammation caused by histamine, Leukotrienes and prostaglandins. It should be noted that this product can not be used for the treatment of asthma with non selective beta blockers, asthma patients with heart disease should be cautious. Common adverse reactions of salmeterol included hypokalemia, abnormal bronchospasm, occasional tremor, Head Pain, and individual palpitations. Common beta-agonists also include: ephedrine, isoproterenol, salbutamol, Terbutaline, formoterol, clorprenaline, tuloterol, clenbuterol, procaterol, salmeterol, bambuterol, methoxamine, rimetterol, bitoterol, heisosolin, Pirbuterol, fenoterol, etc. |
| clinical evaluation | studies have shown that this product 50 μg, 2 times a day inhalation is effective for patients with mild to moderate asthma, for patients with moderate asthma, it may be better to inhale 100 μg twice a day for a long time, up to 12 h or more. Experiments show that this product 50 μg, inhalation 2 times a day, than salbutamol 200 μg, 4 times a day, can improve lung function and reduce the day and night respiratory syndrome. adult patients with bronchial asthma were treated with salmeterol aerosol, 50 μg each time, twice a day (in the morning, before bedtime), and the longest time was 71 weeks. As a result, there was a significant improvement tendency compared with that before administration. After the fourth week of administration, the improvement was 15.0%, moderate improvement was 50%, mild improvement was 72.5%, and the improvement rate of long-term medication was 15.0%, 68.2% and 88.6% respectively. 18 patients with bronchial asthma were given aerosol 25 μg and powder for inhalation 25 μg each time. As a result, FEV10, PEFR, MMEF, V50 and V25 began to improve 25 min after administration, its role lasts 8H. The results of pulmonary function tests at 4h after inhalation were comparable. The total improvement degree and moderate improvement above were both 81.8%, and the effect was exactly the same. for patients with asthma at night, inhalation of 50 μg and 100 μg twice a day can significantly improve the overnight expiratory flow rate and increase the percentage of sleep in patients with asthma at night, these indicators were superior to placebo. Most studies have shown that this product improves the sleep quality of the subjects. |
| Target | Value |
| β2-adrenergic receptor (Cell-free) | 1.5 nM(Ki) |
| Use | bronchodilator. for long-term prevention and treatment of asthma, chronic bronchitis, emphysema with reversible airway obstruction. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:49:11
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