TERBASMIN
terbutaline hemisulfate
CAS: 23031-32-5
Molecular Formula: C24H40N2O10S
TERBASMIN - Names and Identifiers
| Name | terbutaline hemisulfate |
| Synonyms | bricanyl TERBASMIN Bricanyl[R] Terbutaline sulfate terbutaline sulphate terbutaline hemisulfate 1-(3,5-dihydroxyphenyl)-2-tert-butylaminoethanolsulphate 3-benzenediol,5-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-sulfate(2 bis{N-[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]-2-methylpropan-2-aminium} sulfate 2-tert-Butylamino-1-(3,5-dihydroxyphenyl)ethanol, Brethaire, Brethine, Butaliret, Monovent, Terbasmin, Terbul |
| CAS | 23031-32-5 |
| EINECS | 245-386-3 |
| InChI | InChI=1/2C12H19NO3.H2O4S/c2*1-12(2,3)13-7-11(16)8-4-9(14)6-10(15)5-8;1-5(2,3)4/h2*4-6,11,13-16H,7H2,1-3H3;(H2,1,2,3,4) |
| InChIKey | KFVSLSTULZVNPG-UHFFFAOYSA-N |
TERBASMIN - Physico-chemical Properties
| Molecular Formula | C24H40N2O10S |
| Molar Mass | 548.65 |
| Density | 1.1840 (rough estimate) |
| Melting Point | 246-248°C |
| Boling Point | 419.2°C at 760 mmHg |
| Flash Point | 165.3°C |
| Solubility | H2O: soluble100mg/mL, clear to slightly hazy, colorless to yellow |
| Vapor Presure | 8.92E-08mmHg at 25°C |
| Appearance | neat |
| Color | White to Off-White |
| pKa | pKa1 8.8, pKa2 10.1, pKa3 11.2(at 25℃) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.6900 (estimate) |
| Use | For the treatment of bronchial asthma, chronic bronchitis, emphysema and other lung diseases caused by bronchospasm |
| In vitro study | Terbutaline is a relatively selective β2-adrenergic bronchodilator with little effect on α-adrenergic receptors. The drug acts preferentially on β2-adrenergic receptors, but is less selective for β-adrenergic receptors than selective β2-agonists. Terbutaline inhibits antigen-induced histamine release from sensitized human lung tissue, which contributes to the clinical efficacy of the drug during the treatment of allergic asthma. Terbutaline also exhibited competitive reversible inhibition of all BChE variants. The dissociation constants for the UU,FF, and AA homozygotes were 0.18,0.31, and 3.3 mM, respectively. |
| In vivo study | Terbutaline appears to have a greater stimulatory effect on the beta receptors of the bronchi, blood vessels, and uterine smooth muscle (Beta 2 receptors) than on the beta receptors of the Heart (Beta 1 receptors). The drug relaxes smooth muscle and inhibits uterine contraction, but may cause some aerobic exercise stimulation and CNS stimulation. |
TERBASMIN - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R42/43 - May cause sensitization by inhalation and skin contact. R63 - Possible risk of harm to the unborn child |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | DN9000000 |
| HS Code | 2922504500 |
TERBASMIN - Nature
Open Data Verified Data
anhydrous ether crystal, melting point 119~12 2C.
Last Update：2024-01-02 23:10:35
TERBASMIN - Preparation Method
Open Data Verified Data
3,5-= hydroxybenzoic acid and ethanol were reacted under reflux under sulfuric acid catalysis to obtain 3,5-= ethyl hydroxybenzoate. 3,5-= ethyl hydroxybenzoate and benzyl chloride in the presence of potassium carbonate, refluxed for 20h, hydrolyzed to free acid with 5mol/L hydrochloric acid or potassium hydroxide, refluxed to th with thionyl chloride, chlorinated to acyl chloride, reaction with azomethane to form azoacetyl group, and hydrogen bromide to bromoacetyl group, followed by reflux with tert-butylamine for 20H. Finally, Terbutaline is obtained by catalytic hydrogenation in the presence of acetic acid.
Last Update：2025-06-10 22:55:16
TERBASMIN - Application
Open Data Verified Data
Swedish Astra development. Beta 2 A receptor stimulant, there is a role of bronchiectasis. It has a high degree of selectivity for bronchial smooth muscle, and has little effect on the excitation of the heart and no central effect. For bronchial asthma, asthmatic bronchitis, obstructive emphysema and other lung diseases accompanied by bronchospasm. It is especially suitable for asthma patients with hypertension, coronary heart disease and other cardiovascular diseases.
Last Update：2025-08-19 16:24:40
TERBASMIN - Reference Information
| overview | terbutaline sulfate (terbutalin e,TBT), also known as bolicanil, bolicanil, beiliconnor, chuankangsu, terbutaline sulfate, is a selective β2 adrenergic receptor stimulant, which has both antiasthmatic, expectorant and bronchial relaxation effects, it can be used clinically for bronchospasm caused by bronchial asthma, chronic bronchitis, emphysema and other lung diseases, and can also be used to prevent premature delivery and fetal asphyxia. |
| preparation method | fig. 1 is a reaction formula 1.3 for synthesizing terbutaline sulfate. 5-dibenzyloxybenzoic acid (3) is made of 3, 5-dihydroxybenzoic acid (2) by esterification, benzyl protection and KOH hydrolysis. 2.3, 5-dibenzyloxyacetophenone (4) was stirred at room temperature to add 1.1 mmol /ml of methyl lithium ether solution (90ml,99 mmol) dropwise to 3( 9.7g, 28 mmol) of anhydrous ether (60 ml) solution, after 0.5 h, and the reaction continued for 20min. 10% sodium chloride aqueous solution (60ml) was added dropwise at 0~5 ℃, the water layer was extracted with ether (30ml × 2), the ether solution was combined, dried with Na2SO4, evaporated under reduced pressure, and recrystallized with petroleum ether (bp 60~90 ℃) to obtain a white solid. 3.3, 5-dibenzyloxyacetophenone aldehyde (5) 4( 4.6g, 13.8 mmol) is dissolved in diane (14ml), selenium dioxide (1.5g, 13. 5 mmol) is added in aqueous solution (0.8 ml), slowly heated to 80 ℃ within 30 min, after selenium is precipitated, the temperature is raised and refluxed for 3 h. Add activated carbon (0.5g) to decolorize, filter while hot, wash with dialkane aqueous solution (5ml ), evaporate the filtrate under reduced pressure to dry to obtain brown solid, add 90% ethanol (8 ml ), heat and dissolve, precipitate solid after cooling, recrystallize with 70% ethanol to obtain solid 5 with crystalline ethanol. 4.1-( 3, 5-dibenzyloxyphenyl)-2-tert-butylaminoethanol (6) 5( 9.3g, 23.7mmol) was dissolved in methanol (75ml ), tert-butylamine (13.5 ml) and toluene (35ml) were added sequentially, and stirred and refluxed for 3 h. Add activated carbon (0.3g) to decolorize and evaporate to dry under reduced pressure. Add anhydrous ethanol (90ml) to dissolve, add sodium borohydride (0.9g ,23 mmol) in batches at room temperature, add it for about 3h, react at room temperature for 2h, and reflow for 10min. At 0~5 ℃, saturated sodium bicarbonate solution (24ml) was added dropwise, evaporated under reduced pressure, extracted with dichloromethane (30 ml × 2), washed with water (15ml × 2), and dried with Na2SO4. Steam dry under reduced pressure and recrystallize with acetone (42 ml) to obtain white solid 6. 5.1-( 3, 5-dihydroxyphenyl) -2-tert-butylamino ethanol (1)6 (28g,69 mmol) was dissolved in absolute ethanol (750ml), Raney nickel (6g) was added, and hydrogenated at 40-50 ℃ for 16h at atmospheric pressure. Steam to dry under reduced pressure, add distilled water (100 ml) to dissolve, adjust pH to 5.6 with 0.1 mol /L sulfuric acid (350 ml), add ethanol (80 ml) to evaporate to dry under reduced pressure. Add methanol (15ml) to dissolve, cool to 5 ℃, precipitate solid, filter, add to methanol (35ml), reflux 5mi n, get white solid 1. |
| clinical application | terbutaline sulfate has the following applications: 1. bronchodilator: used for bronchial asthma, chronic bronchitis, emphysema and other lung diseases caused by bronchospasm, can also treat severe pulmonary heart disease. 2. Intravenous drip: can be used to prevent premature delivery and fetal asphyxia. |
| precautions | 1. forbidden: those who are allergic to this product and those who are allergic to other sympathomimetic amines. 2. patients with hyperthyroidism, coronary heart disease, hypertension and diabetes should be used with caution. 3. A few patients will have finger tremor, headache, palpitations and gastrointestinal disorders and other adverse reactions. 4. High-dose application can cause ketoacidosis in patients with a history of epilepsy. |
| biological activity | Terbutaline Sulfate is a selective β2-adrenergic receptor agonist with an IC50 of 53 nM. |
| Target | Value |
| β2-adrenergic receptor | 53 nM |
| use | β-adrenoceptor agonist; Bronchodilator (bronchodilator). It is used medically for bronchospasm caused by bronchial asthma, chronic bronchitis, emphysema and other lung diseases. |
Last Update：2024-04-09 20:52:54
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