Details
Stereochemistry | RACEMIC |
Molecular Formula | 2C13H21NO3.H2O4S |
Molecular Weight | 576.7 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1.CC(C)(C)NCC(O)C2=CC(CO)=C(O)C=C2
InChI
InChIKey=BNPSSFBOAGDEEL-UHFFFAOYSA-N
InChI=1S/2C13H21NO3.H2O4S/c2*1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15;1-5(2,3)4/h2*4-6,12,14-17H,7-8H2,1-3H3;(H2,1,2,3,4)
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.
CNS Activity
Sources: https://www.drugs.com/pro/albuterol.html
Curator's Comment: Known to be CNS penetrant in rat. Human data not available
Intravenous studies in rats with Albuterol sulfate have demonstrated that Albuterol crosses the blood brain barrier and reaches brain concentrations amounting to approximately 5% of the plasma concentrations.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5673352
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 |
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Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15655528 |
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Target ID: CHEMBL246 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15655528 |
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Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12569076 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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Effects of a range of beta2 adrenoceptor agonists on changes in intracellular cyclic AMP and on cyclic AMP driven gene expression in cultured human airway smooth muscle cells. | 1999 Oct |
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beta-Adrenoceptor stimulation up-regulates phosphodiesterase 4 activity and reduces prostaglandin E2-inhibitory effects in human neutrophils. | 2000 Apr |
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Effect of endogenous and exogenous prostaglandin E(2) on interleukin-1 beta-induced cyclooxygenase-2 expression in human airway smooth-muscle cells. | 2000 Dec |
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Myoclonus secondary to albuterol (salbutamol) instillation. | 2000 May 23 |
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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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Pharmacokinetics and systemic beta2-adrenoceptor-mediated responses to inhaled salbutamol. | 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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Interethnic variability in human drug responses. | 2001 Apr |
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Genetic variation in beta-adrenergic receptors and their relationship to susceptibility for asthma and therapeutic response. | 2001 Apr |
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Permeability of endothelial monolayers to albumin is increased by bradykinin and inhibited by prostaglandins. | 2001 Apr |
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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 |
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Some behavioural effects of antidepressant drugs are time-dependent. | 2001 Feb |
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Effectiveness and safety of the oxytocin antagonist atosiban versus beta-adrenergic agonists in the treatment of preterm labour. The Worldwide Atosiban versus Beta-agonists Study Group. | 2001 Feb |
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Adrenergic airway vascular smooth muscle responsiveness in healthy and asthmatic subjects. | 2001 Feb |
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beta(2)-adrenoceptor agonists inhibit release of eosinophil-activating cytokines from human airway smooth muscle cells. | 2001 Feb |
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Involvement of both G protein alphas and beta gamma subunits in beta-adrenergic stimulation of vascular L-type Ca(2+) channels. | 2001 Feb |
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Randomised controlled study of clinical efficacy of spacer therapy in asthma with regard to electrostatic charge. | 2001 Feb |
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[Bronchial asthma. A combination preparation improves patient compliance]. | 2001 Feb 22 |
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Improvement in aerosol delivery with helium-oxygen mixtures during mechanical ventilation. | 2001 Jan |
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Changes in asthma drug therapy costs for patients receiving chronic montelukast therapy in the U.K. | 2001 Jan |
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Comparison between formoterol 12 microg b.i.d. and on-demand salbutamol in moderate persistent asthma. | 2001 Jan |
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The use of lactose recrystallised from carbopol gels as a carrier for aerosolised salbutamol sulphate. | 2001 Jan |
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Switching from Ventolin CFC to Ventolin HFA is well tolerated and effective in patients with asthma. | 2001 Mar |
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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 |
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Effect of salmeterol on allergen-induced airway inflammation in mild allergic asthma. | 2001 Mar |
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Chronic systemic administration of salmeterol to rats promotes pulmonary beta(2)-adrenoceptor desensitization and down-regulation of G(s alpha). | 2001 Mar |
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Low-dose fluticasone propionate compared with montelukast for first-line treatment of persistent asthma: a randomized clinical trial. | 2001 Mar |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25712316
Curator's Comment: albuterol at 7.25 mg/L (concentrations, mimicking those in the bronchial tree) could modulate pneumococcal biofilm development and antibiotic action using an in vitro model.
7.25 mg/L, pneumococcal biofilm in vitro model.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C48149
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NCI_THESAURUS |
C319
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C47957
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289928
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CHEMBL714
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ALBUTEROL SULFATE
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PRIMARY | Description: A white or almost white powder; odourless. Solubility: Soluble in 4 parts of water; slightly soluble in ethanol (~750 g/l) TS and ether R. Category: Antiasthmatic drug. Storage: Salbutamol sulfate should be kept in a well-closed container, protected from light. Additional information: Even in the absence of light, Salbutamol sulfate is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Definition: Salbutamol sulfate contains not less than 98.0% and not more than 101.0% of C13H21NO3,1/2H2SO4, calculated with reference to the dried substance. | ||
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39859
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142153
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2549
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51022-70-9
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DTXSID10881180
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021SEF3731
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1012633
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256-916-8
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m1480
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DBSALT000257
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100000090564
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SUB04303MIG
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ACTIVE MOIETY
SUBSTANCE RECORD