Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H21NO3 |
Molecular Weight | 239.3107 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1
InChI
InChIKey=NDAUXUAQIAJITI-UHFFFAOYSA-N
InChI=1S/C13H21NO3/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
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 | ( + / - ) |
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 |
---|---|---|
The beta2-adrenergic agonist salbutamol is a potent suppressor of established collagen-induced arthritis: mechanisms of action. | 1999 May 15 |
|
Myoclonus secondary to albuterol (salbutamol) instillation. | 2000 May 23 |
|
Recurrent supraventricular tachycardia as a complication of nebulized albuterol treatment. | 2000 Nov |
|
Profile of ligand binding to the porcine beta2-adrenergic receptor. | 2001 Apr |
|
Pharmacokinetics and systemic beta2-adrenoceptor-mediated responses to inhaled salbutamol. | 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 |
|
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 |
|
Respiratory and cardiovascular effects of WP-934 in guinea pigs. | 2001 Feb |
|
Quantitative determination of clenbuterol, salbutamol and tulobuterol enantiomers by capillary electrophoresis. | 2001 Feb |
|
Mometasone furoate: efficacy and safety in moderate asthma compared with beclomethasone dipropionate. | 2001 Feb |
|
Effects of therapeutic doses of albuterol on beta2-adrenergic receptor density and metabolic changes. | 2001 Feb |
|
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 |
|
Airway vasculature after mycoplasma infection: chronic leakiness and selective hypersensitivity to substance P. | 2001 Feb |
|
Effect of inspiratory flow rate on beta2-agonist induced bronchodilation in mechanically ventilated COPD patients. | 2001 Jan |
|
Improvement in aerosol delivery with helium-oxygen mixtures during mechanical ventilation. | 2001 Jan |
|
Changes in asthma drug therapy costs for patients receiving chronic montelukast therapy in the U.K. | 2001 Jan |
|
Peanut challenge: a retrospective study of 140 patients. | 2001 Jan |
|
The use of lactose recrystallised from carbopol gels as a carrier for aerosolised salbutamol sulphate. | 2001 Jan |
|
Regulation of TNF-alpha-induced eotaxin release from cultured human airway smooth muscle cells by beta2-agonists and corticosteroids. | 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 |
|
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 |
|
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 |
|
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
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
Thu Jul 06 00:03:04 UTC 2023
by
admin
on
Thu Jul 06 00:03:04 UTC 2023
|
Record UNII |
QF8SVZ843E
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
LIVERTOX |
NBK548685
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
WHO-ATC |
R03AK13
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
WHO-VATC |
QR03CC02
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
WHO-ATC |
R03AC02
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
NCI_THESAURUS |
C319
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
WHO-VATC |
QR03AC02
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
NDF-RT |
N0000175779
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
WHO-ATC |
R03AL02
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
WHO-ESSENTIAL MEDICINES LIST |
25.1
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
WHO-VATC |
QR03AK04
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
WHO-VATC |
QR03AL02
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
NCI_THESAURUS |
C48149
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
WHO-ATC |
R03AK04
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
FDA ORPHAN DRUG |
152501
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
WHO-ATC |
R03CC02
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
||
|
NDF-RT |
N0000009922
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
ALBUTEROL
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | Description: A white or almost white, crystalline powder; odourless. Solubility: Soluble in 70 parts of water; soluble in ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Antiasthmatic drug. Storage: Salbutamol should be kept in a well-closed container, protected from light. Definition: Salbutamol contains not less than 98.0% and not more than 101.0% of C13H21NO3, calculated with reference to the dried substance. | ||
|
SUB10422MIG
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
2083
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
100000091629
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
105
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
35763-26-9
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
SUPERSEDED | |||
|
435
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | RxNorm | ||
|
757417
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
DB01001
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
CHEMBL714
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
QF8SVZ843E
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
Albuterol
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
7206
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
2585
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
1012600
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
18559-94-9
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
SALBUTAMOL
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
DTXSID5021255
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
242-424-0
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
558
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
2549
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
D000420
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
M1480
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | Merck Index | ||
|
C215
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY | |||
|
QF8SVZ843E
Created by
admin on Thu Jul 06 00:03:04 UTC 2023 , Edited by admin on Thu Jul 06 00:03:04 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT | |||
|
SALT/SOLVATE -> PARENT | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
|
||
|
SALT/SOLVATE -> PARENT | |||
|
TARGET -> AGONIST |
SHORT-ACTING
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
BINDER->LIGAND | |||
|
PARENT->INNOVATOR |
|
||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
IN-VIVO
URINE
|
||
|
METABOLITE INACTIVE -> PARENT |
catalysed almost exclusively by sulphotransferase (SULT) 1A3
|
||
|
METABOLITE -> PARENT |
catalysed almost exclusively by sulphotransferase (SULT) 1A3
MAJOR
PLASMA
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Volume of Distribution | PHARMACOKINETIC |
|
|
|||
ORAL BIOAVAILABILITY | PHARMACOKINETIC |
|
ORAL, EXTENDED-RELEASE TABLET PHARMACOKINETIC |
|
||
Tmax | PHARMACOKINETIC |
|
HYDROFLUOROALKANE (HFA) INHALER PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
|
||
Biological Half-life | PHARMACOKINETIC |
|
|
|||
Volume of Distribution | PHARMACOKINETIC |
|
|
|||
MAXIMUM TOLERATED DOSE | TOXICITY |
|
EXTENDED-RELEASE TABLET PHARMACOKINETIC |
|
||
Biological Half-life | PHARMACOKINETIC |
|
ORAL, INHALATION PHARMACOKINETIC PHARMACOKINETIC |
|
||