ESMOLOL HCL
Esmolol hydrochloride
CAS: 81161-17-3
Molecular Formula: C16H26ClNO4
ESMOLOL HCL - Names and Identifiers
| Name | Esmolol hydrochloride |
| Synonyms | asl8052 Brevibloc ESMOLOL HCL ESMOLOL HYDROCHLORIDE Esmolol hydrochloride MONOCLONAL ANTI-EDG-4 (ENDOTHELIAL CELL 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy] benxzenepropanoic Acid Methyl Ester Hydrochloride 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)benzenepropanoicacidmethylest Methyl 3-[4-(2-hydroxy-3-propan-2-ylamino-propoxy)phenyl]propanoate hydrochloride 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benxzenepropanoic Acid Methyl Ester Hydrochloride 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzenepropanoic acid methyl ester hydrochloride hydrochloride |
| CAS | 81161-17-3 |
| EINECS | 636-017-0 |
| InChI | InChI=1/C16H25NO4.ClH/c1-12(2)17-10-14(18)11-21-15-7-4-13(5-8-15)6-9-16(19)20-3;/h4-5,7-8,12,14,17-18H,6,9-11H2,1-3H3;1H |
ESMOLOL HCL - Physico-chemical Properties
| Molecular Formula | C16H26ClNO4 |
| Molar Mass | 331.83 |
| Density | 1.026 |
| Melting Point | 48-50°C |
| Water Solubility | Slightly soluble |
| Solubility | H2O: soluble12mg/mL |
| Appearance | buffered aqueous solution |
| Color | White to Off-White |
| Storage Condition | −20°C |
| Physical and Chemical Properties | This product is white or white crystalline powder; Odorless, slightly bitter taste. This product is easily soluble in water, soluble in ethanol or chloroform, and slightly soluble in ethyl acetate. Melting Point: 85~92 ℃ |
| In vitro study | Esmolol contains an asymmetric center and exists as a pair of enantiomers, The (-)-enantiomer is active, the ()-enantiomer is inactive, this is similar to other P-inhibitors with an oxypropranol amine nucleus. Esmolol has the function of rapid onset and inactivation, and the main active sites of Esmolol are sinoatrial node and atrioventricular node conduction system. |
| In vivo study | Injection of Esmolol (20 mg/kg) in septic rats can improve myocardial oxygen utilization and protect myocardial function. Esmolol (5 mg/kg, I. v.) acting on rabbits, a dose-dependent decrease in heart rate (HR) and a dose-dependent decrease in mean arterial pressure (MAP) were produced, with the maximum percentage reductions being 13% and 38.2, respectively. Esmolol (300 mg/kg) can significantly reduce heart rate, heart rate systolic pressure product, left ventricular contraction, cardiac output, right ventricular relative refractory period, and inhibit atrioventricular node conduction in dogs, and improve the efficiency of the right ventricular refractory period and the preload of the left ventricle. In addition, Esmolol (300 mg/kg) significantly reduced isoproterenol-induced increases in heart rate and ventricular contractions in dogs. |
ESMOLOL HCL - Risk and Safety
| Risk Codes | 52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | 61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| WGK Germany | - |
| RTECS | DA8346000 |
| HS Code | 2922199695 |
ESMOLOL HCL - Standard
Authoritative Data Verified Data
This product is methyl 4-[2-hydroxy-3-(isopropylamino) propoxy] phenylpropionate hydrochloride. The dry product shall contain no less than 98.5% of C16H25N04 • HCl.
Last Update：2024-01-02 23:10:35
ESMOLOL HCL - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder; Odorless.
- This product is easily soluble in water, soluble in ethanol or chloroform, and slightly soluble in ethyl acetate.
melting point
The melting point of this product (General 0612) is 85~92°C (when measured, the temperature is 0.5°C per minute).
Last Update：2022-01-01 14:20:53
ESMOLOL HCL - Differential diagnosis
Authoritative Data Verified Data
- take about 0.3g of this product, add 1ml of water to dissolve, add 2ml of hydroxylamine hydrochloride test solution and 1ml of 28% potassium hydroxide ethanol solution, heat to boiling, cool, and add dilute hydrochloric acid to make it acidic, the solution was purplish red when ferric chloride solution was added dropwise.
- take this product, add water to dissolve and dilute to make about 0. The lmg solution, as determined by UV-Vis spectrophotometry (General 0401), has a maximum absorption at a wavelength of 222mn and 274nm and a minimum absorption at a wavelength of 245nm.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 635).
- the aqueous solution of this product was chloride identification (1) of the reaction (General 0301).
Last Update：2022-01-01 14:20:54
ESMOLOL HCL - Exam
Authoritative Data Verified Data
acidity
take this product, add water to dissolve and dilute to make a solution containing 20mg esmolol hydrochloride in each lml, and determine it according to law (General rule 0631). The pH value should be 4.5~6.0.
clarity and color of solution
take this product, add water to dissolve and dilute to make a solution containing 20mg esmolol hydrochloride in each lml, the solution should be clear and colorless; If the color is developed, it shall not be deeper than the yellow or yellow-green standard colorimetric solution No. 1 (General rule 0901 method 1).
Related substances
take this product, add mobile phase A to dissolve and dilute to make about 1 ml of esmolol Hydrochloride 1.0 mg of the solution was used as the test solution; An appropriate amount was quantitatively diluted with mobile phase A to prepare A solution containing about 2% of esmolol hydrochloride per 1 ml, and the solution was shaken to obtain A control solution. The related substances of esmolol hydrochloride were determined according to the method. If there are impurity peaks in the chromatogram of the test solution, the peak area of impurity I shall not be greater than the main peak area of the control solution (0.2% ) , other single impurity peak area shall not be greater than 1.5 times (0.3%) of the main peak area of the control solution, and the sum of each impurity peak area shall not be greater than 5 times (1.0%) of the main peak area of the control solution. The chromatogram of the test solution is 0.1 times smaller than the main peak area of the control solution, and the peak is negligible (0.02%).
loss on drying
take this product, at 60°C under reduced pressure drying to constant weight, weight loss should not exceed 1.0% (General rule 0831).
sterile
take this product, dissolve it with appropriate solvent, and treat it by membrane filtration method. Check it according to law (General rule 1101).
pyrogen
take this product, add 0.9% pyrogen-free gasification sodium sterilized aqueous solution for injection to dissolve and dilute to prepare a solution containing esmolol hydrochloride 2mg per 1 ml, and check according to law (General 1142), dose according to the rabbit body weight per lkg slow injection of 5ml, should comply with the provisions.
Other
should comply with the relevant provisions under the injection (General Principle 0102).
Last Update：2022-01-01 14:20:55
ESMOLOL HCL - Content determination
Authoritative Data Verified Data
measured by high performance liquid chromatography (General 0512).
chromatographic conditions and system suitability test
silica gel bonded with eighteen alkyl silane as filler; Acetonitrile-methanol-phosphate buffer (3.0g of potassium dihydrogen phosphate, dissolved in water and diluted to 650ml)(15:20:65) mobile phase, flow rate of 1.0ml per minute, detection wavelength of 222nm; Theoretical plate number according to esmolol peak is not less than 2000.
assay
The content under the item of difference in loading is suitable for children, precision weighing, adding water to dissolve esmolol hydrochloride and quantitatively diluting it into a solution containing about 50ug esmolol hydrochloride per 1 ml, as a sample solution, 20ul was accurately measured, and human liquid chromatograph was injected to record the chromatogram. Another reference substance of esmolol hydrochloride was accurately weighed and determined by the same method. According to the external standard method to calculate the peak area, that is.
Last Update：2022-01-01 14:20:55
ESMOLOL HCL - Category
Authoritative Data Verified Data
Same as esmolol hydrochloride.
Last Update：2022-01-01 14:20:56
ESMOLOL HCL - Storage
Authoritative Data Verified Data
light shielding, closed storage.
Last Update：2022-01-01 14:20:56
ESMOLOL HCL - Specifications
Authoritative Data Verified Data
0.1g
Last Update：2022-01-01 14:20:56
ESMOLOL HCL - Reference Information
| Overview | esmolol hydrochloride Hcl chemical name (±)-3-{4-[2-hydroxy-3-(1-methylethylamino) propoxy] phenyl} propionic acid methyl ester hydrochloride, is a selective beta 1 blocker of aryloxypropylamine ultra short-acting, mainly through the competition of catecholamine binding sites to inhibit beta 1 receptors, with slow resting and exercise heart rate, lower blood pressure and myocardial oxygen consumption and other effects. At the same time, it has the characteristics of rapid onset, high bioavailability, short half-life, definite curative effect and low side effects. At present, it is mainly used for the treatment of Supraventricular arrhythmia and acute myocardial ischemia in clinic, unstable angina, postoperative hypertension and other diseases also have obvious curative effect. |
| preparation method | 1. P-hydroxybenzaldehyde was prepared by condensation, reduction, esterification, amination and salt formation. The synthetic route is shown in Figure 1. Figure 1 shows the synthetic route of esmolol Hydrochloride 1(1) P-hydroxyphenyl acrylic acid (3) P-benzaldehyde, malonic acid, pyridine, aniline and toluene stirred reflux at 85 °c for 2H. After being slightly cold, pour into cold water. The aqueous layer was separated, acidified to Ph 2 with hydrochloric acid, placed, and the crystals were filtered off, washed with water, and dried to give P-hydroxyphenylacrylic acid (3) as an off-white solid. (2) P-hydroxyphenylpropanoic acid (4) p-hydroxyphenylacrylic acid (3) was dissolved in an aqueous sodium hydroxide solution, and then W-2 type Raney-Ni was added thereto to raise the temperature to 85 ° C., and hydrazine hydrate was added dropwise with stirring. After addition, the reaction was continued at 85 °c and filtered. The filtrate was adjusted to pH 1 with hydrochloric acid. The mixture was placed in a refrigerator, and needle-like crystals were precipitated, filtered, washed with water, and dried to obtain compound (4). (3) methyl p-hydroxyphenylpropionate (5) was put into p-hydroxyphenylpropionic acid, methanol, concentrated sulfuric acid and 3A Molecular sieve, and refluxed for 72H. Methanol was removed under reduced pressure, and the residual solution was dissolved in toluene and washed with water. The toluene layer was dried over anhydrous magnesium sulfate and treated with activated carbon. (4) methyl 3-[ 4-(2, 3-epoxypropoxy) phenyl] propanoate (6) above oil (5), epichlorohydrin, potassium carbonate, acetone, the mixture was heated and refluxed for 24h for filtration, and the solvent was removed under reduced pressure. The residual solution was dissolved in toluene, washed with an aqueous sodium hydroxide solution, and then washed with water. After the toluene layer was dried over magnesium sulfate, the solvent was removed, An oil (6) was obtained. (5) esmolol hydrochloride (1) compound (6), isopropylamine, methanol, refluxed for 4H. After the solvent was removed under reduced pressure, the oil was dissolved in methanol, and saturated hydrogen chloride ether solution was added dropwise under ice cooling to Ph 2. After standing for 8H, the mixture was filtered and washed with anhydrous ether, recrystallization from isopropanol and vacuum drying gave (1) as a white solid. With p-hydroxybenzaldehyde as starting material, it was prepared by etherification, aminolysis, condensation with malonic acid and esterification followed by Palladium-carbon/Atmospheric pressure catalytic hydrogenation. Its synthetic route is shown in figure 2. Figure 2 is the synthetic route of esmolol hydrochloride 2(1)4-( 2, 3-epoxypropoxy) benzaldehyde (3) from 2 to colorless liquid 3(2)4-[2-hydroxy-3-[(1-methylethyl) amino] propoxy] benzaldehyde (4) in a reaction flask equipped with a stirrer and a reflux condenser, add 3, isopropylamine and methanol. Water bath heating, stirring Reflux reaction 1.5 h. Methanol and excess isopropylamine were distilled off at atmospheric pressure to give a pale yellow viscous liquid 4, which was used directly in the next step without purification. (3)3-[4-[2-hydroxy-3-[(1-methylethyl) amino] propoxy] phenyl] Acrylic acid hydrochloride (5)4 and malonic acid, the pyridine was heated to 105-110 ° C. In a three-head flask equipped with a stirrer, a reflux condenser and a thermometer for 6H. Cool to room temperature, add water, stir to dissolve solids, Adjust to Ph 2 with concentrated hydrochloric acid. Upon standing, a white solid precipitated. The filter cake was filtered, washed with ice water, dried, and recrystallized from anhydrous ethanol to obtain white powdery solid 5. (4) methyl 3-[4-[2-hydroxy-3-[(1-methylethyl) amino] propoxy] phenyl] acrylate hydrochloride (6) in a 250ml flask, add 5 and methanol. After the solid was dissolved by stirring, dry hydrogen chloride gas was introduced to saturation. A Soxhlet extractor containing a molecular sieve was installed, and the mixture was heated and refluxed for 20H under magnetic stirring. Most of the methanol was recovered by distillation, and the concentrated solution was cooled and crystallized. After filtration, drying and recrystallization with anhydrous ethanol, white crystals 6 were obtained. (5) esmolol hydrochloride (1) 6, methanol and 5% Palladium on carbon were sequentially added to a 100ml Erlenmeyer flask. At room temperature, with magnetic stirring, hydrogen gas was introduced until it was no longer absorbed. Filter and wash the filter cake with methanol. The filtrate and washings were combined, the methanol was recovered by distillation, and the residue was left to solidify at room temperature. The crude product was recrystallized from a methanol-diethyl ether mixed solvent to give a white powdery solid 1. |
| Application | is mainly used for the treatment of Supraventricular arrhythmia and acute myocardial ischemia, for acute myocardial infarction, unstable angina, postoperative hypertension and other diseases have obvious curative effect. (2016-01-22) |
| adverse reaction | The most important adverse reaction was hypotension, followed by peripheral ischemia, confusion, Head Pain, irritability, Fatigue, vomit, et al. |
| biological activity | Esmolol (ASL8052) is a cardiac selective B receptor blocker, used to control the rapid heartbeat or abnormal heart rate rhythm. |
| Target | Value |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:12
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