U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ALBUTEROL

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

HIDE SMILES / InChI

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

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
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
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 Thu Jul 06 00:03:04 UTC 2023
Edited
by admin
on Thu Jul 06 00:03:04 UTC 2023
Record UNII
QF8SVZ843E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALBUTEROL
HSDB   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
1,3-BENZENEDIMETHANOL, .ALPHA.(SUP 1)-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-4-HYDROXY-
Common Name English
ALBUTEROL [ORANGE BOOK]
Common Name English
ALBUTEROL [HSDB]
Common Name English
SALBUTAMOL [EP IMPURITY]
Common Name English
SALBUTAMOL
EP   INN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
VENTOLINE
Common Name English
ETINOLINE
Common Name English
salbutamol [INN]
Common Name English
ALBUTEROL [USAN]
Common Name English
ALBUTEROL [USP MONOGRAPH]
Common Name English
ALBUTEROL [USP-RS]
Common Name English
SALBUTAMOL [EP MONOGRAPH]
Common Name English
SALBUTAMOL [WHO-IP]
Common Name English
SCH 13949W
Code English
SALBUTAMOL [MART.]
Common Name English
NSC-757417
Code English
Salbutamol [WHO-DD]
Common Name English
(±)-1,3-BENZENEDIMETHANOL, .ALPHA.(SUP 1)-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-4-HYDROXY-
Common Name English
ALBUTEROL [MI]
Common Name English
ALBUTEROL [VANDF]
Common Name English
SCH-13949W
Code English
SALBUTAMOLUM [WHO-IP LATIN]
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
WHO INTERNATIONAL PHARMACOPEIA
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.
EVMPD
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
PUBCHEM
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
SMS_ID
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
DRUG CENTRAL
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
CAS
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
RXCUI
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
NSC
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
DRUG BANK
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
ChEMBL
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
FDA UNII
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
LACTMED
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
HSDB
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
INN
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
RS_ITEM_NUM
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
CAS
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
WIKIPEDIA
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
EPA CompTox
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
ECHA (EC/EINECS)
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
IUPHAR
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
CHEBI
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
MESH
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
MERCK INDEX
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
NCI_THESAURUS
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
DAILYMED
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
CHLOROFLUOROCARBON INHALER
PHARMACOKINETIC
NEBULIZER
PHARMACOKINETIC
DRY POWDER METERED DOSE INHALER
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
MAXIMUM TOLERATED DOSE TOXICITY EXTENDED-RELEASE TABLET
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC ORAL, INHALATION
PHARMACOKINETIC
ORAL, TABLET AND SYRUP
PHARMACOKINETIC