Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H21NO3.ClH |
Molecular Weight | 275.772 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1
InChI
InChIKey=OWNWYCOLFIFTLK-UHFFFAOYSA-N
InChI=1S/C13H21NO3.ClH/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15;/h4-6,12,14-17H,7-8H2,1-3H3;1H
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 | ClH |
Molecular Weight | 36.461 |
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
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 |
---|---|---|---|
Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15655528 |
|||
Target ID: CHEMBL246 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15655528 |
|||
Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12569076 |
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 Date8.4006719E11 |
PubMed
Title | Date | PubMed |
---|---|---|
Comparative study of extended release albuterol sulfate and long-acting inhaled salmeterol xinafoate in the treatment of nocturnal asthma. | 1999 Aug |
|
Hypokalemia and salbutamol therapy in asthma. | 1999 Jan |
|
The beta2-adrenergic agonist salbutamol is a potent suppressor of established collagen-induced arthritis: mechanisms of action. | 1999 May 15 |
|
Effect of endogenous and exogenous prostaglandin E(2) on interleukin-1 beta-induced cyclooxygenase-2 expression in human airway smooth-muscle cells. | 2000 Dec |
|
Recurrent supraventricular tachycardia as a complication of nebulized albuterol treatment. | 2000 Nov |
|
The effect of acute alteration in oxygen tension on the bronchodilator response to salbutamol in vitro and in vivo in man. | 2001 |
|
Profile of ligand binding to the porcine beta2-adrenergic receptor. | 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 |
|
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 |
|
Pediatric pre-hospital advanced life support care in an urban setting. | 2001 Feb |
|
Beta2-agonist exerts differential effects on the development of cord blood T cells but not on peripheral blood T cells. | 2001 Feb |
|
Regular inhaled salbutamol : effect on airway responsiveness to methacholine and adenosine 5'-monophosphate and tolerance to bronchoprotection. | 2001 Feb |
|
Are asthma medications and management related to deaths from asthma? | 2001 Jan |
|
The role of patient training in the management of seasonal rhinitis and asthma: clinical implications. | 2001 Jan |
|
A hooded exposure chamber method for semiquantitative latex aeroallergen challenge. | 2001 Jan |
|
Catecholamine inotropes as growth factors for Staphylococcus epidermidis and other coagulase-negative staphylococci. | 2001 Jan 15 |
|
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 |
|
Effect of salmeterol on allergen-induced airway inflammation in mild allergic asthma. | 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 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:49:57 UTC 2023
by
admin
on
Sat Dec 16 11:49:57 UTC 2023
|
Record UNII |
P12862PDAK
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DTXSID80965587
Created by
admin on Sat Dec 16 11:49:57 UTC 2023 , Edited by admin on Sat Dec 16 11:49:57 UTC 2023
|
PRIMARY | |||
|
100000181252
Created by
admin on Sat Dec 16 11:49:57 UTC 2023 , Edited by admin on Sat Dec 16 11:49:57 UTC 2023
|
PRIMARY | |||
|
6452399
Created by
admin on Sat Dec 16 11:49:57 UTC 2023 , Edited by admin on Sat Dec 16 11:49:57 UTC 2023
|
PRIMARY | |||
|
P12862PDAK
Created by
admin on Sat Dec 16 11:49:57 UTC 2023 , Edited by admin on Sat Dec 16 11:49:57 UTC 2023
|
PRIMARY | |||
|
51293-66-4
Created by
admin on Sat Dec 16 11:49:57 UTC 2023 , Edited by admin on Sat Dec 16 11:49:57 UTC 2023
|
PRIMARY | |||
|
39006-83-2
Created by
admin on Sat Dec 16 11:49:57 UTC 2023 , Edited by admin on Sat Dec 16 11:49:57 UTC 2023
|
SUPERSEDED |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |