23031-25-6

23031-25-6 - Names and Identifiers

Name	5-(1-Hydroxy-2-tert-butylamino-ethyl)benzene-1,3-diol
Synonyms	C07129 Bambuterol EP Impurity A 5-(1-Hydroxy-2-tert-butylamino-ethyl)benzene-1,3-diol 5-[(S)-1-Hydroxy-2-(tert-butylamino)ethyl]benzene-1,3-diol (S)-α-[(tert-Butylamino)methyl]-3,5-dihydroxybenzyl alcohol (R)-α-[(tert-Butylamino)methyl]-3,5-dihydroxybenzyl alcohol rac-5-[(R*)-2-[(1,1-Dimethylethyl)amino]-1-hydroxyethyl]-1,3-benzenediol
CAS	23031-25-6
EINECS	245-385-8

23031-25-6 - Physico-chemical Properties

Molecular Formula	C12H19NO3
Molar Mass	225.28
Density	1.0951 (rough estimate)
Melting Point	119-122°
Boling Point	366.8°C (rough estimate)
Refractive Index	1.4596 (estimate)
Use	Uses for bronchial asthma, chronic asthmatic bronchitis, obstructive Pulmonary emphysema and other lung disease bronchospasm

23031-25-6 - Nature

acidity coefficient (pKa)

pKa 8.70(H2O t = 25 I = 0.01) (Uncertain);10.09(H2O t = 25 I = 0.01) (Uncertain)

Last Update：2024-04-10 22:29:15

23031-25-6 - Uses and synthesis methods

overview

Terbutaline (Terbutaline, TBL) is also known as Tebuterol. The drug name is metahydroxysalbutamol, metahydroxysalbutamol, etc. It is a kind of phenethylamine drugs and is a powerful β2-receptor agonist. This product can act on β2 receptors, expand bronchial smooth muscle, inhibit the release of endogenous spasmodic substances and edema caused by endogenous mediators, improve the ability of bronchial mucosal cilia clearance, and also expand uterine smooth muscle. The selectivity to bronchial β2 receptors is greater than salbutamol, so the excitatory effect on the heart is very small, only 1% of isoproterenol. Since it is not inactivated by catechol oxygen-site methyltransferase or monoamine oxidase metabolism in the body, the action time is longer. Clinically, it is mainly used to dilate the trachea and increase lung ventilation. It can be used for symptoms such as asthma, obstructive pneumonia, smooth muscle spasm and shock.

With the increasing national monitoring of common β2-agonists such as clenbuterol, ractopamine and salbutamol, TBL, as a β2-agonist with equivalent pharmacological effects, has been illegally used as a feed additive in the production of animal-derived food. The long-term application of β2-receptor agonists such as TBL in the production of animal-derived foods will not only cause animal welfare problems such as damage to the animal itself, but also cause accumulated residues of TBL in edible animal tissues. It often causes clinical symptoms such as palpitations and muscle tremors in consumers, especially for patients with heart disease, diabetes and hypertension. In view of the obvious harm of β2-agonists such as TBL, the Ministry of Agriculture, the Ministry of Health and the State Drug Administration jointly issued Announcement No. 176, listing TBL in the list of drugs prohibited from use in feed and animal drinking water.

Salbutamol

Salbutamol is a selective β2 receptor agonist, which can selectively excite the β2 receptor of bronchial smooth muscle and has a strong bronchodilation effect. For patients with asthma, the bronchodilation effect is at least the same as isoproterenol. Inhibition of the release of allergic reaction mediators by sensitized cells such as mast cells is also related to the antispasmodic effect of bronchial smooth muscle. The agonistic effect on the beta 1 receptor of the heart is weak, so its increased heart rate effect is only 1/10 of isoproterenol. It is used to prevent and treat bronchospasm in patients with bronchial asthma, asthmatic bronchitis and emphysema. Stop the attack with aerosol inhalation, prevent the attack can be taken orally.

Pharmacokinetics

The gastrointestinal tract is not completely absorbed and is susceptible to a wide range of first-pass effects. Oral administration takes effect after 30 minutes, reaching the maximum effect at 2-4 hours, and the maintenance time is 5-8 hours; aerosol inhalation takes effect after 5-15 minutes, reaching the maximum effect at 0.5-1 hours, and can maintain the maximum effect for 4 hours. In the liver or intestinal wall combined into sulfate and glucuronide. This product is excreted in urine in the form of inactive metabolites and original drugs.

Overview, use, pharmacokinetics, adverse reactions, etc. of terbutaline

adverse reactions

a few cases have headache, palpitations, tremor and tetanic spasm and other central nervous symptoms and mild gastrointestinal disorders.

precautions

1. People with hypertension, coronary heart disease, hyperthyroidism and pregnant women should use it with caution.

2.β2 receptor agonists have the effect of increasing blood sugar, so diabetic patients should first control blood sugar when starting to use this product.

3.β2 receptor agonists have been successfully used in the acute treatment of severe ischemic heart failure, but these drugs have the possibility of causing arrhythmia, so they must be considered when treating individual patients.

4. The degree of side effects depends on the dose and route of administration. Gradually adding a small dose to a therapeutic dose often reduces side effects. Most side effects can disappear naturally within 1 to 2 weeks after the start of medication.

drug interactions 1. The use of other adrenal receptor agonists can increase the efficacy, but the adverse reactions may also be aggravated.

2. The combination of this product and theophylline drugs can increase the curative effect, but adverse reactions such as palpitations may also aggravate.

3. Non-selective β-blockers can partially or completely inhibit the effects of β-agonists.

use

Used to treat bronchial asthma, asthmatic bronchitis and emphysema, etc.

production method

3, 5-dihydroxybenzoic acid and ethanol react under the catalysis of sulfuric acid to obtain ethyl 3, 5-dihydroxybenzoate. In the presence of potassium carbonate, ethyl 3, 5-dihydroxybenzoate and benzyl chloride were refluxed for 20h, hydrolyzed to free acid with 5mlo/L hydrochloric acid or potassium hydroxide, refluxed with thionyl chloride for 1h, chlorinated to acyl chloride, reacted with azomethane to form azo acetyl group, reacted with hydrogen bromide to become bromoacetyl group, and then refluxed with tert-. Finally, terbutaline is obtained by catalytic hydrogenation in the presence of acetic acid.

Last Update：2024-04-10 22:29:15