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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
Structure of ALBUTEROL ADIPATE DIETHANOLATE

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

HIDE SMILES / InChI

Molecular Formula C6H10O4
Molecular Weight 146.1412
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C13H21NO3
Molecular Weight 239.3107
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C2H6O
Molecular Weight 46.0684
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROVENTIL-HFA

Approved Use

Albuterol 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 Date

8.4006719E11
PubMed

PubMed

TitleDatePubMed
Nocturnal asthma uncontrolled by inhaled corticosteroids: theophylline or long-acting beta2 agonists?
2001
The effect of acute alteration in oxygen tension on the bronchodilator response to salbutamol in vitro and in vivo in man.
2001
Zafirlukast: an update of its pharmacology and therapeutic efficacy in asthma.
2001
Profile of ligand binding to the porcine beta2-adrenergic receptor.
2001 Apr
Pharmacokinetics and systemic beta2-adrenoceptor-mediated responses to inhaled salbutamol.
2001 Apr
Use of a long-acting inhaled beta2-adrenergic agonist, salmeterol xinafoate, in patients with chronic obstructive pulmonary disease.
2001 Apr
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
The utility of peak flow, symptom scores, and beta-agonist use as outcome measures in asthma clinical research.
2001 Apr
Evaluation of salmeterol or montelukast as second-line therapy for asthma not controlled with inhaled corticosteroids.
2001 Apr
Comparative in vivo lung delivery of hydrofluoroalkane-salbutamol formulation via metered-dose inhaler alone, with plastic spacer, or with cardboard tube.
2001 Apr
Fluticasone propionate/salmeterol combination.
2001 Apr
Efficacy of nebulized epinephrine versus salbutamol in hospitalized infants with bronchiolitis.
2001 Apr
Interethnic variability in human drug responses.
2001 Apr
Genetic variation in beta-adrenergic receptors and their relationship to susceptibility for asthma and therapeutic response.
2001 Apr
Up-regulation of uncoupling proteins by beta-adrenergic stimulation in L6 myotubes.
2001 Apr 13
A combination of fluticasone and salmeterol for asthma.
2001 Apr 16
beta-adrenergic receptor stimulation selectively inhibits IL-12p40 release in microglia.
2001 Apr 27
The diagnosis and treatment of cough.
2001 Apr 5
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
Cumulative and single-dose design to assess the bronchodilator effects of beta2-agonists in individuals with asthma.
2001 Feb
Involvement of both G protein alphas and beta gamma subunits in beta-adrenergic stimulation of vascular L-type Ca(2+) channels.
2001 Feb
[Bronchial asthma. A combination preparation improves patient compliance].
2001 Feb 22
Effect of inspiratory flow rate on beta2-agonist induced bronchodilation in mechanically ventilated COPD patients.
2001 Jan
Efficacy of a home-made spacer with acute exacerbation of bronchial asthma: a randomized controlled trial.
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
Peanut challenge: a retrospective study of 140 patients.
2001 Jan
Catecholamine inotropes as growth factors for Staphylococcus epidermidis and other coagulase-negative staphylococci.
2001 Jan 15
Exhalation of H2O2 and thiobarbituric acid reactive substances (TBARs) by healthy subjects.
2001 Jan 15
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
Hyperosmolar diabetic non-ketotic coma, hyperkalaemia and an unusual near death experience.
2001 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
Clinical predictors of health-related quality of life depend on asthma severity.
2001 Mar
The effect of salmeterol on markers of airway inflammation following segmental allergen challenge.
2001 Mar
Albuterol delivery in a neonatal ventilated lung model: Nebulization versus chlorofluorocarbon- and hydrofluoroalkane-pressurized metered dose inhalers.
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
Effect of salmeterol on allergen-induced airway inflammation in mild allergic asthma.
2001 Mar
Nebivolol and airway responsiveness in the rabbit.
2001 Mar 23
Functional properties of atypical beta-adrenoceptors on the guinea pig duodenum.
2001 Mar 23
Solubility prediction of salmeterol xinafoate in water--dioxane mixtures.
2001 Mar 23
Patents

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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:23:53 UTC 2023
Edited
by admin
on Sat Dec 16 08:23:53 UTC 2023
Record UNII
289U58VGDE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALBUTEROL ADIPATE DIETHANOLATE
Common Name English
HEXANEDIOIC ACID, COMPD. WITH .ALPHA.1-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-4-HYDROXY-1,3-BENZENEDIMETHANOL AND ETHANOL (1:1:2)
Systematic Name English
Code System Code Type Description
FDA UNII
289U58VGDE
Created by admin on Sat Dec 16 08:23:53 UTC 2023 , Edited by admin on Sat Dec 16 08:23:53 UTC 2023
PRIMARY
CAS
177985-44-3
Created by admin on Sat Dec 16 08:23:53 UTC 2023 , Edited by admin on Sat Dec 16 08:23:53 UTC 2023
PRIMARY
PUBCHEM
177325
Created by admin on Sat Dec 16 08:23:53 UTC 2023 , Edited by admin on Sat Dec 16 08:23:53 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE