Salbutamol Chemical Properties
- Melting point:157-160℃
- Boiling point:381.97°C (rough estimate)
- Density 1.0700 (rough estimate)
- refractive index 1.4800 (estimate)
- storage temp. ?20°C
- solubility Sparingly soluble in water, soluble in ethanol (96 per cent).
- pkapKa 9.07(H2O t = 25.0±0.05 I = 0.10) (Uncertain);10.37(H2O t = 25.0±0.05 I = 0.10) (Uncertain)
- form neat
- Water Solubility 17.95g/L(25 ºC)
- Merck 13,215
- BRN 6405698
- Stability:Stable, but light sensitive. Incompatible with strong oxidizing agents.
- CAS DataBase Reference18559-94-9(CAS DataBase Reference)
- EPA Substance Registry System1,3-Benzenedimethanol, .alpha.1-[[(1,1-dimethylethyl)amino]methyl]-4-hydroxy- (18559-94-9)
Salbutamol Usage And Synthesis
- DescriptionSalbutamol is a short-acting, selective β2-adrenergic receptor agonist. Like other β2-adrenergic receptor drugs that are breathed in through the mouth, salbutamol can relax the muscles in the lung and open the bronchial tubes to relieve breathing difficulty. They relieve cough, wheezing, shortness of breath, and troubled breathing by increasing the flow of air through the bronchial tubes.
Salbutamol is generally used to treat or prevent bronchospasm caused by bronchial asthma, chronic bronchitis, and other chronic bronchopulmonary disorders such as chronic obstructive pulmonary disorder (COPD). It is also used prevent wheezing caused by exercise (exercise induced bronchospasm).
It is marketed as Airomir®; AirSalb®; Asmasal Clickhaler®; Asmavent®; Easyhaler® Salbutamol; Pulvinal® Salbutamol; Salamol®; Salbulin®; Ventolin®.
- References https://www.drugbank.ca
- Chemical Propertiessolid
- OriginatorVentolin ,Allen and Hanburys ,UK ,1969
- Usesimmune suppressant, antineoplastic, antiviral
- Usesshort-acting b2-adrenergic agonist, asthma therapeutic
- DefinitionChEBI: A member of the class of phenylethanolamines that is 4-(2-amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol having a tert-butyl group attached to the nirogen atom. It acts as a beta-adrenergic agonist used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).
- Manufacturing Process(a) α1-Benzyl-tert-butylaminomethyl-4-hydroxym-xylene-α1,α3-diol: 3.0 g of
5-(N-benzyl-N-tert-butylglycyl)-salicylic acid methyl ester hydrochloride in 40
ml of water was basified with sodium bicarbonate solution and extracted into
ether. The ethereal solution was dried over MgSO4 and evaporated and the
basic residue in 20 ml of dry tetrahydrofuran was added with stirring to 1.0 g
of lithium aluminum hydride in 100 ml of dry tetrahydrofuran, over a period of
5 minutes. The light gelatinous precipitate that formed was stirred and
refluxed for 8 hours after which time 7 ml of water was carefully added and
the solvents were removed under reduced pressure.
The residue was acidified with dilute hydrochloric acid and brought to pH 8 with sodium hydroxide and sodium bicarbonate. The mixture was filtered and the filtrate and orange solid were separately extracted with chloroform. The combined, dried, chloroform solutions were evaporated to give 22 g of the crude basic triol as an orange solid, when triturated with ether. A portion of the material was recrystallized from ether/light petroleum (BP 40-60°C) to give a white solid, MP 109-111°C.
In an alternative process, sodium borohydride was used as the reducing agent, as follows:
36 g of 2-(benzyl-tert-butylamino)-4'-hydroxy-3'-hydroxymethyl acetophenone, hydrochloride was shaken with 100 ml of 10% sodium carbonate solution and 100 ml of ethyl acetate. The ethyl acetate layer was separated, washed with water, dried over anhydrous sodium sulfate and evaporated in vacuum.
The residual gum was dissolved in 360 ml of ethanol and cooled to 15°C in an ice/water bath, 8 g of sodium borohydride was then added in portions over 30 minutes while maintaining the temperature at 15-20°C. After a further 30 minutes at 20°C the solution was stirred at room temperature for 2 hours. The solution was again cooled in ice and 250 ml of 2 N sulfuric acid were slowly added, then the solution was evaporated in vacuum until the ethanol had been removed. The clear aqueous solution was then treated with 250 ml of 10% sodium carbonate solution and the oil which precipitated was extracted into ethyl acetate. The ethyl acetate layer was washed with sodium carbonate solution, then with water, and was dried over anhydrous sodium sulfate and evaporated in vacuum, to a small volume. Petroleum ether (BP 40-60°C) was added, and after standing overnight a white solid was obtained. This was filtered off to give 23 g of the product, MP 110-114°C.
(b) α1-tert-Butylaminomethyl-4-hydroxy-m-xylene-α1,α3-diol: 0.8 g of α1- benzyl-tert-butyl-aminomethyl-4-hydroxy-m-xylene-α1,α3-diol in 20 ml of ethanol and 2 ml of water was shaken with hydrogen in presence of 0.50 g of pre-reduced 10% palladium on charcoal catalyst. When uptake of hydrogen was complete, the solution was filtered and evaporated under reduced pressure to give 0,4 g of the base as a colorless oil which yielded a white solid, MP 144-145°C when triturated with ether/cyclohexane. Recrystallization from ethyl acetate-cyclohexane gave a white solid, MP 147-149°C.
- brand nameProventil (Schering); Ventolin (GlaxoSmithKline).
- Therapeutic FunctionBronchodilator
- Biological FunctionsLevalbuterol is the R-(–)-isomer of albuterol and is available only in solution to be administered via nebulizer. Because it is the active isomer, the dose is fourfold less than that of albuterol. Pirbuterol is the pyridine isostere of albuterol. It has pharmacokinetics similar to albuterol but is half as potent at the β2-receptor. Pirbuterol is only available as an inhaler, whereas albuterol comes in tablet, syrup, solution, and aerosol formulations.
- Clinical UseAlbuterol has the N-t-butyl and a salicyl alcohol phenyl ring, which gives it optimal β2-selectivity. It is resistant to COMT and slowly metabolized by MAO, giving it good oral bioavailability. Its onset by inhalation is within 5 minutes, with a duration of action between 4 and 8 hours. It currently is the drug of choice for relief of the acute bronchospasm of an asthmatic attack.
- Side effectsAdverse effects of pirbuterol are nervousness, tremor, and headache, which is less than the profile for albuterol, which adds nausea, vomiting, dizziness, hypertension, insomnia, tachycardia, and palpitations.
- BENZYL ALBUTEROL METHYL ESTER R-SALBUTAMOL HCL,Salbutamol 4-Benzyl Albuterol R-ALBUTEROL HYDROCHLORIDE Salbutamol-tert-butyl-d9 Salbutamol Kresoxim-methyl Methyl Ethanolamine Musk xylene CHLOROPHOSPHONAZO III Thiophanate-methyl m-Xylene Diethylaminoethanol Xylene Methyl bromide SALBUTAMOL BASE,SALBUTAMOL HEMISULFATE SALT,SALBUTAMOL HEMISULFATE,SALBUTAMOL SULPHATE,SALBUTAMOL SULFATE,SALBUTAMOL SULPHATE, IMP. C (EP): (1RS)-2-[(1,1-DIMETHYLETHYL)AMINO]-1-(4-HYDROXY-3-METHYL-PHENYL)ETHANOL MM(CRM STANDARD),SALBUTAMOL SULPHATE, EP STANDARD,SALBUTAMOL SULPHATE, BP STANDARD,SALBUTAMOL SULPHATE, MM(CRM STANDARD) Diphenylsilanediol
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