Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C13H21NO3.C6H10O4.2C2H6O |
| Molecular Weight | 477.5888 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCO.CCO.OC(=O)CCCCC(O)=O.CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1
InChI
InChIKey=IOIVZFGXQDBEKZ-UHFFFAOYSA-N
InChI=1S/C13H21NO3.C6H10O4.2C2H6O/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15;7-5(8)3-1-2-4-6(9)10;2*1-2-3/h4-6,12,14-17H,7-8H2,1-3H3;1-4H2,(H,7,8)(H,9,10);2*3H,2H2,1H3
Albuterol is a short acting beta2-adrenergic receptor agonist. Albuterol effectively alleviates bronchospasm due to bronchial asthma, chronic bronchitis, and other chronic bronchopulmonary disorders such as COPD. In vitro studies and in vivo pharmacologic studies have demonstrated that albuterol has a preferential effect on beta2-adrenergic receptors compared with isoproterenol. While it is recognized that beta2-adrenergic receptors are the predominant receptors in bronchial smooth muscle, data indicate that there is a population of beta2-receptors in the human heart existing in a concentration between 10% and 50%. The precise function of these receptors has not been established. The pharmacologic effects of beta-adrenergic agonist drugs, including albuterol, are at least in part attributable to stimulation through beta-adrenergic receptors of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3',5'- adenosine monophosphate (cyclic AMP). Increased cyclic AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells. Albuterol has been shown in most controlled clinical trials to have more effect on the respiratory tract, in the form of bronchial smooth muscle relaxation, than isoproterenol at comparable doses while producing fewer cardiovascular effects. Albuterol is longer acting than isoproterenol in most patients by any route of administration because it is not a substrate for the cellular uptake processes for catecholamines nor for catechol-O-methyl transferase.
Originator
Curator's Comment: On arriving at Allen and Hanburys in 1961 as Research Director, David set himself the task of finding a more selective bronchodilator than isoprenaline, the non-selective ß-adrenoceptor agonist, which was widely in use at the time but caused unwanted effects on the heart at doses that caused bronchodilation, even when inhaled. This led to the discovery of salbutamol, as the first selective ß2-adrenoceptor agonist for the treatment of bronchospasm associated with airway diseases such as asthma
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL213 |
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Target ID: CHEMBL246 |
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Target ID: CHEMBL210 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | PROVENTIL-HFA Approved UseAlbuterol sulfate inhalation solution is indicated for the relief of bronchospasm in patients 2 years of age and older with reversible obstructive airway disease and acute attacks of bronchospasm. Launch Date1996 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The effect of acute alteration in oxygen tension on the bronchodilator response to salbutamol in vitro and in vivo in man. | 2001 |
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| Onset of action of single doses of formoterol administered via Turbuhaler in patients with stable COPD. | 2001 |
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| Onset of bronchodilation of budesonide/formoterol vs. salmeterol/fluticasone in single inhalers. | 2001 |
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| Profile of ligand binding to the porcine beta2-adrenergic receptor. | 2001 Apr |
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| The role of domiciliary nebulizers in managing patients with severe COPD. | 2001 Apr |
|
| Comparative efficiency of commercial and improvised spacer device in acute bronchial asthma. | 2001 Apr |
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| The utility of peak flow, symptom scores, and beta-agonist use as outcome measures in asthma clinical research. | 2001 Apr |
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| Evaluation of salmeterol or montelukast as second-line therapy for asthma not controlled with inhaled corticosteroids. | 2001 Apr |
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| Comparative in vivo lung delivery of hydrofluoroalkane-salbutamol formulation via metered-dose inhaler alone, with plastic spacer, or with cardboard tube. | 2001 Apr |
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| Fluticasone propionate/salmeterol combination. | 2001 Apr |
|
| A combination of fluticasone and salmeterol for asthma. | 2001 Apr 16 |
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| The diagnosis and treatment of cough. | 2001 Apr 5 |
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| Requirement of additional adenylate cyclase activation for the inhibition of human eosinophil degranulation by phosphodiesterase IV inhibitors. | 2001 Apr 6 |
|
| Respiratory and cardiovascular effects of WP-934 in guinea pigs. | 2001 Feb |
|
| Some behavioural effects of antidepressant drugs are time-dependent. | 2001 Feb |
|
| Quantitative determination of clenbuterol, salbutamol and tulobuterol enantiomers by capillary electrophoresis. | 2001 Feb |
|
| Pediatric pre-hospital advanced life support care in an urban setting. | 2001 Feb |
|
| Effects of therapeutic doses of albuterol on beta2-adrenergic receptor density and metabolic changes. | 2001 Feb |
|
| Beta2-agonist exerts differential effects on the development of cord blood T cells but not on peripheral blood T cells. | 2001 Feb |
|
| Clinical equivalence of salmeterol/fluticasone propionate in combination (50/100 microg twice daily) when administered via a chlorofluorocarbon-free metered dose inhaler or dry powder inhaler to patients with mild-to-moderate asthma. | 2001 Feb |
|
| Cumulative and single-dose design to assess the bronchodilator effects of beta2-agonists in individuals with asthma. | 2001 Feb |
|
| Advair: combination treatment with fluticasone propionate/salmeterol in the treatment of asthma. | 2001 Feb |
|
| Adrenergic airway vascular smooth muscle responsiveness in healthy and asthmatic subjects. | 2001 Feb |
|
| [Salmeterol plus fluticasone--a powerful team. New combined preparation improves compliance]. | 2001 Feb 8 |
|
| Efficacy of a home-made spacer with acute exacerbation of bronchial asthma: a randomized controlled trial. | 2001 Jan |
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| The pharmacokinetics of levosalbutamol: what are the clinical implications? | 2001 Jan |
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| Improvement in aerosol delivery with helium-oxygen mixtures during mechanical ventilation. | 2001 Jan |
|
| Regular versus as-needed short-acting inhaled beta-agonist therapy for chronic obstructive pulmonary disease. | 2001 Jan |
|
| Are asthma medications and management related to deaths from asthma? | 2001 Jan |
|
| Changes in asthma drug therapy costs for patients receiving chronic montelukast therapy in the U.K. | 2001 Jan |
|
| Comparison between formoterol 12 microg b.i.d. and on-demand salbutamol in moderate persistent asthma. | 2001 Jan |
|
| A randomized, 12-week, double-blind, placebo-controlled study comparing formoterol dry powder inhaler with albuterol metered-dose inhaler. | 2001 Jan |
|
| Clinical characteristics of asthmatic patients prescribed various beta-agonist metered-dose inhalers at Yamagata University Hospital. | 2001 Jan |
|
| Randomized comparison of a dry powder inhaler and metered dose inhaler with spacer in management of children with asthma. | 2001 Jan |
|
| Factors affecting the efficiency of aerosol therapy with pressurised metered-dose inhalers through plastic spacers. | 2001 Jan 12 |
|
| Catecholamine inotropes as growth factors for Staphylococcus epidermidis and other coagulase-negative staphylococci. | 2001 Jan 15 |
|
| [Acute pulmonary edema caused by tocolytic therapy with salbutamol]. | 2001 Jan 27 |
|
| Salmeterol and fluticasone propionate given as a combination. Lack of systemic pharmacodynamic and pharmacokinetic interactions. | 2001 Jan-Feb |
|
| Effect of polymorphism of the beta(2)-adrenergic receptor on response to regular use of albuterol in asthma. | 2001 Jan-Mar |
|
| Towards evidence based emergency medicine: best BETs from the Manchester Royal Infirmary. Salbutamol and ipratropium in COPD. | 2001 Mar |
|
| Assessment of forearm vasodilator responses to acetylcholine and albuterol by strain gauge plethysmography: reproducibility and influence of strain gauge placement. | 2001 Mar |
|
| Switching from Ventolin CFC to Ventolin HFA is well tolerated and effective in patients with asthma. | 2001 Mar |
|
| The effect of salmeterol on markers of airway inflammation following segmental allergen challenge. | 2001 Mar |
|
| The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: the role of potassium channels and vasoactive intestinal peptide receptors. | 2001 Mar |
|
| Single-isomer beta-agonists. | 2001 Mar |
|
| Chronic systemic administration of salmeterol to rats promotes pulmonary beta(2)-adrenoceptor desensitization and down-regulation of G(s alpha). | 2001 Mar |
|
| Salmeterol and conventional asthma therapy. | 2001 Mar |
|
| Low-dose fluticasone propionate compared with montelukast for first-line treatment of persistent asthma: a randomized clinical trial. | 2001 Mar |
|
| New combination therapies for asthma. | 2001 Mar |
|
| Nebivolol and airway responsiveness in the rabbit. | 2001 Mar 23 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Albuterol also supplied as 2 mg tablets: usual dosage - 2 or 4 mg three or four times a day.
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=87b8cd3c-2849-4b50-b63e-9ea379165c07
Intravenous salbutamol is commonly used to treat children with severe asthma unresponsive to inhaled β2-agonist therapy, usual dose is 4ug/kg.
https://www.drugs.com/uk/ventolin-injection-500mcg-1ml-leaflet.html
Two inhalations repeated every 4 to 6 hours (aerosol, metered)
Route of Administration:
Respiratory
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289U58VGDE
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177985-44-3
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177325
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admin on Sat Dec 16 08:23:53 GMT 2023 , Edited by admin on Sat Dec 16 08:23:53 GMT 2023
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
