3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionic acid methyl ester
Esmolol
CAS: 81147-92-4;103598-03-4
Molecular Formula: C16H25NO4
3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionic acid methyl ester - Names and Identifiers
3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionic acid methyl ester - Physico-chemical Properties
| Molecular Formula | C16H25NO4 |
| Molar Mass | 295.37 |
| Density | 1.026 |
| Melting Point | 48-50 °C |
| Boling Point | 430.2±40.0 °C(Predicted) |
| Flash Point | 214°C |
| Water Solubility | Slightly soluble |
| Vapor Presure | 3.62E-08mmHg at 25°C |
| Merck | 14,3700 |
| pKa | 13.88±0.20(Predicted) |
3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionic acid methyl ester - Risk and Safety
| RTECS | DA8345500 |
3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionic acid methyl ester - Nature
Open Data Verified Data
- The oily substance slowly formed crystals at room temperature and had a melting point of 48 to 50 °c. Soluble in methanol.
- esmolol hydrochloride: crystallized from methanol monoethyl ether. Insoluble in ether. Melting point 85~86 deg C.
Last Update：2024-01-02 23:10:35
3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionic acid methyl ester - Preparation Method
Open Data Verified Data
p-hydroxybenzaldehyde and malonic acid are dissolved in toluene, refluxed in the presence of an organic base, and condensed and decarboxylated to give p-hydroxyphenylacrylic acid. P-hydroxyphenylacrylic acid was hydrogenated in a mixed solvent of dioxane and water under 10% palladium-carbon catalysis to obtain p-hydroxyphenylpropionic acid. P-hydroxyphenylpropionic acid and methanol in sulfuric acid catalysis, reflux esterification of methyl p-hydroxyphenylpropionate, and then in alkaline solution, bromide decasix alkyl trimethyl ammonium (CTAB) in the presence of, and epichlorohydrin reflux, 3[4-(2,3 A epoxy propyl oxy) phenyl] methyl propionate. Finally, the mixture was refluxed with isopropylamine in methanol to give esmolol. A solution of saturated hydrogen chloride in diethyl ether was added dropwise to methanol to give esmolol hydrochloride as a white solid. Or p-methoxybenzaldehyde as raw material, in the presence of sodium and ethyl acetate condensation to generate 3 p-methoxy phenyl ethyl acrylate, hydrogenation reduction to 3 p-methoxy phenyl propionic acid ethyl ester, hydrolysis to generate 3 p-hydroxyphenyl propionic acid, by methyl esterification, it is reacted with epichlorohydrin and finally with isopropylamine to form esmolol.
Last Update：2022-01-01 09:10:05
3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionic acid methyl ester - Use
Open Data Verified Data
U. S. Du pert development, first launched in the United States in 1987. Ultra-short-acting beta-adrenergic receptor blockers. In vivo metabolism, it is easy to be hydrolyzed by esterase into carboxylic acid with almost no Beta blocking activity, which has fast onset and short duration, definite curative effect and little side effect. Selectively blocking β-receptors has little effect on the bronchi and is beneficial for patients with chronic obstructive pulmonary disease. It is an ideal drug for the treatment of supraventricular tachyarrhythmia, acute myocardial ischemia and postoperative hypertension. For patients undergoing coronary artery surgery, prophylactic use of the product can significantly reduce hypertension, tachycardia and arrhythmia caused by intubation and surgical stimulation.
Last Update：2022-01-01 09:10:06
3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionic acid methyl ester - Reference Information
| Overview | Esmolol (Esmolol), also known as Ailuo, Emolol, Brevibloc, chemical name 4 {[3-[(1-Methylethyl) amino]-2 hydroxy] propoxy} Methyl phenylpropionate hydrochloride, code-named ASL-8052, was founded by Critical Care in 1982 and first listed in the United States in 1987, it is an ultra-short-acting heart-selective β1-receptor blocker. It has no intrinsic sympathomimetic activity and membrane stabilization at the therapeutic dose. It also has an inhibitory effect on the β2 receptor of tracheal and vascular smooth muscle at large doses. It is characterized by fast onset and short action time. Clinically, it is mainly used for supraventricular tachycardia that occurs during anesthesia; it can also be used for supraventricular tachyarrhythmia after myocardial infarction or myocardial infarction, as well as acute unstable angina pectoris. It can also be used for rapid antihypertensive treatment of hypertension during perioperative period and anesthesia. Fig. 1 is the structural formula of esmolol |
| pharmacological action | selective adrenergic beta 1 receptor blocker with short acting time. It mainly acts on β1 receptors in myocardium, and also blocks β2 receptors in trachea and vascular smooth muscle in large doses. There is no intrinsic sympathomimetic or membrane stabilizing effect at the therapeutic dose. Antiarrhythmic mainly plays a role by inhibiting the stimulation of adrenaline on the pacemakers and slowing the conduction of the atrioventricular node. Its main site of action is the sinus node and atrioventricular node conduction system. The mechanism of antihypertensive is not completely clear, similar to propranolol, but when producing the same β-receptor blockade, it is better than other selective and non-selective β-blockers such as metoprolol and propranolol. The drug can lower blood pressure. |
| pharmacokinetics | effective 3~5 min after intravenous injection, 6~10min effect reached a peak, lasting 20 min. Half-life 9.2 min. In the blood circulation, it is rapidly hydrolyzed by erythrocyte lactase to inactive metabolites and methanol. 0.6% ~ 0.98% is excreted from urine as a prototype. |
| apply | 1. treat rapid supraventricular tachycardia with an effective rate of 66% ~ 79%. It can also be used to treat atrial fibrillation and atrial flutter, with effective rates of 76% and 60% respectively. 2. Coronary heart disease, angina pectoris. 3. Postoperative hypertension. |
| usage and dosage | 1. treat supraventricular arrhythmia 0.5mg/(kg min),1min intravenous injection, followed by 0.05mg/(kg min) intravenous injection for 4min. The ideal curative effect can be maintained. If the curative effect is not good, the same load will be given and maintained at 0.1mg/(kg min). The dose can be adjusted according to the condition at an increase of 50 μg/(kg · min). The extreme amount should not exceed 0.3mg/(kg min). 2. Intraoperative control of hypertension is completed by intravenous injection within 30 seconds of 80mg load, followed by 0.15mg/(kg min) maintenance, which can achieve the goal quickly. Slowly controlled supraventricular arrhythmia. 3. Injection (10mg or 25mg/mL) must be diluted first. |
| precautions | 1. severe bradycardia (including sinus bradycardia), atrioventricular block above degree I, cardiogenic shock, and severe heart failure are contraindicated in patients with bronchial asthma. 2. The occurrence of hypotension is dose-dependent, so the recommended maintenance amount is generally not more than 0.2 mg/kg per minute. If the blood pressure is low, the application of this product should be closely monitored. When the blood pressure is too low, the minimum maintenance amount should be reduced, which can be reversed within 30 minutes. 3. It should be used with caution when accompanied by heart failure, generally starting from a small dose. 4. This product should not be used for blood pressure increase caused by vasoconstriction mainly due to cooling. 5. Use with warfarin, digoxin, morphine or succinylcholine, should be cautious. 6. Patients with diabetes should be especially careful when using this product, because beta blockers can cover up tachycardia caused by hypoglycemia. 7. Infusion concentration shall not exceed 10mg/ ml. Not compatible with sodium bicarbonate injection. |
| adverse reactions | most adverse reactions are mild and transient. The most important adverse reaction is hypotension. Death has been reported using esmolol to control ventricular rate alone. 1. Cardiovascular system: hypotension (asymptomatic hypotension, symptomatic hypotension), occasional bradycardia, chest pain, heart block. 2. Mental nervous system: dizziness, headache, lethargy, inattention, irritability, etc., occasionally fatigue, paresthesia, anxiety or depression, fantasy, etc. 3. Respiratory system: tracheal spasm, dyspnea, nasal congestion. 4. Gastrointestinal tract: nausea, vomiting, occasionally dry mouth, constipation, abdominal discomfort or wrong taste. 5. Skin: flushing, edema, erythema, induration at the injection site, occasional thrombophlebitis. 6. Others: occasionally urinary retention, speech disorders, abnormal vision, shoulder and back pain, chills, fever, etc. |
| contraindications | bronchial asthma, cardiogenic shock, heart block (Ⅱ to Ⅲ degree atrioventricular block), severe or acute heart failure, sinus bradycardia And those who are allergic to this product are contraindicated. (2016-01-22) |
| drug interaction | 1. when combined with non-steroidal anti-inflammatory drugs, blood pressure can be increased. 2. When combined with warfarin, the blood concentration of this product seems to increase, but it has little clinical significance. 3. When combined with digoxin, the blood concentration of digoxin can be increased, which can lead to prolonged atrioventricular conduction time. 4. When combined with morphine, the steady-state blood concentration of this product will increase. 5. The combination with succinylcholine can prolong the neuromuscular blocking effect of succinylcholine. 6. This product will reduce the efficacy of epinephrine. 7. The combination of this product and verapamil for patients with cardiac dysfunction will lead to cardiac arrest. 8. Significant sinus bradycardia may occur in combination with amiodarone. 9. When combined with verapamil, there is an additive negative inotropic effect, which can cause bradycardia, blood pressure drop, congestive heart failure and conduction block. 10. Combined with calcium antagonists, it has an additive inhibitory effect on atrioventricular conduction and sinoatrial node function. |
| use | treat frequent arrhythmia, acute, myocardial ischemia and hypertension during or after surgery. |
| production method | 1. p-hydroxybenzaldehyde and malonic acid are dissolved in toluene, and in the presence of organic base, reflux, condensation and decarboxylation to obtain p-hydroxyphenylacrylic acid. p-hydroxyphenylacrylic acid is hydrogenated in a mixed solvent of dioxane and water under 10% palladium-carbon catalysis to obtain p-hydroxyphenylpropionic acid. Under the catalysis of sulfuric acid, p-hydroxyphenylpropanoic acid and methanol are refluxed and esterified to obtain methyl p-hydroxyphenylpropanate, and then in alkaline solution, in the presence of decyltrimethylammonium bromide (CTAB), and epichlorohydrin is refluxed to obtain 3[4(2, 3-epoxypropoxy) phenyl] methyl propionate. Finally, in methanol, it is refluxed with isopropylamine to obtain esmolol; in methanol, the ether solution of saturated hydrogen chloride is added dropwise to obtain white solid esmolol hydrochloride. Or use p-methoxybenzaldehyde as a raw material, condensed with ethyl acetate in the presence of sodium to form ethyl 3-p-methoxyphenylacrylate, hydrogenated and reduced to ethyl 3-p-methoxyphenylpropionate, Hydrolysis produces 3-p-hydroxyphenylpropionic acid, which is methylated, then reacted with epichlorohydrin, and finally reacted with isopropylamine to form esmolol. 2. Using p-methoxybenzaldehyde as raw material, it is condensed with ethyl acetate in the presence of sodium to form ethyl 3-p-methoxyphenylacrylate, which is hydrogenated and reduced to ethyl 3-p-methoxyphenylpropionate, hydrolyzed to generate 3-p-hydroxyphenylpropionic acid, which is then methylated, then reacted with epichloropropane, and then reacted with isopropylamine to generate Eisi |
Last Update：2024-04-09 19:05:07
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