(-)-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)-hydroxy-3-(2-morpholino-carbonylamino)ethylamino]propoxy]phenylpropionate monohydrochloride
Landiolol
CAS: 133242-30-5
Molecular Formula: C25H39N3O8
(-)-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)-hydroxy-3-(2-morpholino-carbonylamino)ethylamino]propoxy]phenylpropionate monohydrochloride - Names and Identifiers
(-)-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)-hydroxy-3-(2-morpholino-carbonylamino)ethylamino]propoxy]phenylpropionate monohydrochloride - Physico-chemical Properties
| Molecular Formula | C25H39N3O8 |
| Molar Mass | 509.59 |
(-)-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)-hydroxy-3-(2-morpholino-carbonylamino)ethylamino]propoxy]phenylpropionate monohydrochloride - Reference Information
| β1 receptor blocker | esmolol (esmolol) is currently the most commonly used β1 receptor blocker during perioperative period. besides reducing heart rate, large doses can lead to blood pressure drop. Landiolol (landiolol) is a new compound obtained on the basis of the chemical structure of esmolol. It has higher cardiac selectivity. The selectivity of β1 receptor is 251 times that of β2 receptor. It mainly antagonizes β1 receptor existing in the heart, and improves tachycardia arrhythmia by inhibiting the increase of cardiac beat number caused by catecholamines. This product has no intrinsic sympathomimetic activity and membrane stabilization effect. The T1/2 in the blood of this product is extremely short, about 4min, which is different from the existing β-receptor blockers. It is mainly used for tachycardia and atrial fibrillation during surgery. Treatment of atrial flutter. Esmolol is an ultra-short-acting, highly selective β-blocker. This product has no endogenous sympathomimetic effect, and the therapeutic dose has no membrane stabilizing effect. Mainly in the myocardium, it blocks the β1 receptor by competing for catecholamine binding sites. It has the effects of slowing resting and exercise heart rate, lowering blood pressure, and reducing myocardial oxygen consumption. This product can accelerate ischemia after coronary artery occlusion The recovery of myocardium reduces the infarct area, and its physiological effects are limited to the sinoatrial node and atrioventricular node. It is used to quickly control the frequency or cardioversion of supraventricular tachycardia, atrial fibrillation or flutter before and after surgery or during surgery and other emergency situations. It can also be used to control non-compensatory sinus tachycardia and treat myocardial ischemia or infarction. |
| use | for tachycardia arrhythmia (atrial fibrillation, atrial flutter and sinus tachycardia) during surgery. (2015-12-28) |
| synthesis method | reverse synthesis analysis landiolol contains a long-chain structure and contains ester groups, amides, ethers and β-amino alcohols that are easier to cut. Therefore, these strategy keys can be cut off step by step to obtain simple starting materials. First, the β-amino alcohol is cut to obtain amine 2 and epoxide 3. Secondly, the ether bond in epoxide 3 was cut to get S-epoxy bromopropane 4 and phenol 5. Finally, the ester bond in phenol 5 was cut off to give acid 7 and chloroketal 6. Both chirality in landeolol molecule can be constructed by chiral source method. Figure 1 is the anti-synthesis route of landiolol synthesis route with 3-(4-hydroxyphenyl) propionic acid 7 and chloro-ketal 6 as starting materials for esterification, the resulting ester of phenolic hydroxyl and S-epoxy bromopropane into ether 3. Finally, amine 2 was used to nucleophilic attack the epoxy group to obtain landiolol 1 in 43% yield. Fig. 1 shows the synthesis route of landi lol |
| adverse reactions | the total incidence of adverse reactions of this product is 15.6%(80 cases/513 cases), the main adverse reactions were hypotension in 60 cases (11.7%), bradycardia in 3 cases (0.6%), ST-tip depression in 2 cases (0.4%), pulmonary artery pressure increase in 1 case (0.2%), wheezing in 1 case (0.2%), ALT increase in 4 cases (0.9%), AST increase in 3 cases (0.7%), and no serious adverse reactions were found. |
| precautions | patients with cardiogenic shock, allergic to this product, obvious cardiac insufficiency, Ⅱ ~ Ⅲ degree atrioventricular block, and severe sinus bradycardia are contraindicated. During surgical anesthesia, myocardial depression, bronchial asthma, congestive heart failure, diabetes, elderly patients, liver insufficiency, thyroid disease, hypotension, and peripheral vascular disease should be used with caution. It should be slow to stop the drug and avoid sudden arrest. |
| clinical evaluation | during surgery, sympathetic nerve excitement is caused due to various stimuli on the body such as endotracheal intubation and extubation, skin incision and surgical operation, which releases too much catecholamines, increases cardiac beat number and easily causes tachycardia arrhythmia. Especially for patients with ischemic heart disease and hypertension, the increase in the number of heart beats will increase the load of the heart, which will cause coronary artery ischemia. Landelol is a drug developed for this. Clinical trials have shown that for emergency tachyarrhythmias, such as atrial fibrillation, atrial flutter, and sinus tachycardia, this product is administered 0.125 mg/kg within 1 min, followed by 0.04 mg/(kg · min) intravenous administration, 2~3 min after administration, the heart rate is significantly slowed down, during the continuous administration process, tachyarrhythmia can be effectively controlled. |
Last Update：2024-04-10 22:29:15
![(-)-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)-hydroxy-3-(2-morpholino-carbonylamino)ethylamino]propoxy]phenylpropionate monohydrochloride](http://res.chembk.com/assets/str/2d/1/13/133242-30-5.png)
Supplier List
Spot supply
Product Name: Landiolol Monomer Visit Supplier Webpage Request for quotationCAS: 133242-30-5
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Spot supply
Product Name: Landiolol Monomer Visit Supplier Webpage Request for quotationCAS: 133242-30-5
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
View History