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Identification
NameSalbutamol
Accession NumberDB01001  (APRD00553)
Typesmall molecule
Groupsapproved
Description

Salbutamol is a short-acting, selective beta2-adrenergic receptor agonist used in the treatment of asthma and COPD. It is 29 times more selective for beta2 receptors than beta1 receptors giving it higher specificity for pulmonary beta receptors versus beta1-adrenergic receptors located in the heart. Salbutamol is formulated as a racemic mixture of the R- and S-isomers. The R-isomer has 150 times greater affinity for the beta2-receptor than the S-isomer and the S-isomer has been associated with toxicity. This lead to the development of levalbuterol, the single R-isomer of salbutamol. However, the high cost of levalbuterol compared to salbutamol has deterred wide-spread use of this enantiomerically pure version of the drug. Salbutamol is generally used for acute episodes of bronchospasm caused by bronchial asthma, chronic bronchitis and other chronic bronchopulmonary disorders such as chronic obstructive pulmonary disorder (COPD). It is also used prophylactically for exercise-induced asthma.

Structure
Thumb
Synonyms
SynonymLanguageCode
AlbuterolNot AvailableUSAN
LevalbuterolNot AvailableNot Available
ProventilNot AvailableNot Available
SalbutamolNot AvailableNot Available
Salts
Name/CAS Structure Properties
Salbutamol Sulfate
Thumb
  • InChI Key: BNPSSFBOAGDEEL-UHFFFAOYNA-N
  • Monoisotopic Mass: 576.271666328
  • Average Mass: 576.7
DBSALT000257
Brand names
NameCompany
AccuNebNot Available
AerolinNot Available
AiromirNot Available
AsmolNot Available
AsthalinNot Available
AsthaventNot Available
ProAirTeva
PROAIRHFANot Available
ProventilNot Available
SalamolNot Available
VentilanGlaxoSmithKline
VentolinGlaxoSmithKline
VentolineGlaxoSmithKline
VENTOLINHFANot Available
VentorlinGlaxoSmithKline
VoSpireNot Available
XopenexNot Available
Brand mixtures
Brand NameIngredients
CombiventIpratropium Bromide + Salbutamol Sulfate
DuoNebIpratropium bromide + Salbutamol
Gen-Combo SterinebsIpratropium Bromide + Salbutamol Sulfate
Categories
CAS number18559-94-9
WeightAverage: 239.3107
Monoisotopic: 239.152143543
Chemical FormulaC13H21NO3
InChI KeyNDAUXUAQIAJITI-UHFFFAOYSA-N
InChI
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
IUPAC Name
4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
SMILES
CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenols and Derivatives
Direct parentPhenols and Derivatives
Alternative parentsSecondary Alcohols; Polyols; 1,2-Aminoalcohols; Primary Alcohols; Enols; Dialkylamines; Polyamines
Substituents1,2-aminoalcohol; secondary alcohol; polyol; secondary amine; enol; secondary aliphatic amine; polyamine; primary alcohol; alcohol; amine; organonitrogen compound
Classification descriptionThis compound belongs to the phenols and derivatives. These are compounds containing a phenol moiety, which is a benzene bearing an hydroxyl group.
Pharmacology
IndicationFor symptomatic relief and prevention of bronchospasm due to bronchial asthma, chronic bronchitis, and other chronic bronchopulmonary disorders such as COPD.
PharmacodynamicsSalbutamol (INN) or albuterol (USAN), a moderately selective beta(2)-receptor agonist similar in structure to terbutaline, is widely used as a bronchodilator to manage asthma and other chronic obstructive airway diseases. The R-isomer, levalbuterol, is responsible for bronchodilation while the S-isomer increases bronchial reactivity. The R-enantiomer is sold in its pure form as Levalbuterol. The manufacturer of levalbuterol, Sepracor, has implied (although not directly claimed) that the presence of only the R-enantiomer produces fewer side-effects.
Mechanism of actionSalbutamol is a beta(2)-adrenergic agonist and thus it stimulates beta(2)-adrenergic receptors. Binding of albuterol to beta(2)-receptors in the lungs results in relaxation of bronchial smooth muscles. It is believed that salbutamol increases cAMP production by activating adenylate cyclase, and the actions of salbutamol are mediated by cAMP. Increased intracellular cyclic AMP increases the activity of cAMP-dependent protein kinase A, which inhibits the phosphorylation of myosin and lowers intracellular calcium concentrations. A lowered intracellular calcium concentration leads to a smooth muscle relaxation and bronchodilation. In addition to bronchodilation, salbutamol inhibits the release of bronchoconstricting agents from mast cells, inhibits microvascular leakage, and enhances mucociliary clearance.
AbsorptionSystemic absorption is rapid following aerosol administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hydrolyzed by esterases in tissue and blood to the active compound colterol. The drug is also conjugatively metabolized to salbutamol 4'-O-sulfate.

SubstrateEnzymesProduct
Salbutamol
Not Available
Salbutamol 4-O-sulfateDetails
Route of eliminationApproximately 72% of the inhaled dose is excreted in the urine within 24 hours, 28% as unchanged drug and 44% as metabolite.
Half life1.6 hours
ClearanceNot Available
ToxicityLD50=1100 mg/kg (orally in mice)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9812
Blood Brain Barrier - 0.9659
Caco-2 permeable - 0.7112
P-glycoprotein substrate Substrate 0.684
P-glycoprotein inhibitor I Non-inhibitor 0.8781
P-glycoprotein inhibitor II Non-inhibitor 0.9673
Renal organic cation transporter Non-inhibitor 0.8974
CYP450 2C9 substrate Non-substrate 0.7897
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Non-substrate 0.7074
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9197
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9287
CYP450 3A4 substrate Non-inhibitor 0.9343
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8834
Ames test Non AMES toxic 0.8409
Carcinogenicity Non-carcinogens 0.8863
Biodegradation Not ready biodegradable 0.9734
Rat acute toxicity 2.5275 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9564
hERG inhibition (predictor II) Non-inhibitor 0.9288
Pharmacoeconomics
Manufacturers
  • Armstrong pharmaceuticals inc
  • Genpharm inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Pliva inc
  • Schering corp sub schering plough corp
  • Glaxosmithkline
  • Teva global respiratory research llc
  • 3m pharmaceuticals inc
  • Dey lp
  • Actavis mid atlantic llc
  • Apotex inc richmond hill
  • Apotex inc
  • Bausch and lomb inc
  • Cobalt laboratories inc
  • Copley pharmaceutical inc
  • Hi tech pharmacal co inc
  • Holopack international
  • Landela pharmaceutical
  • Nephron pharmaceuticals corp
  • Nephron corp
  • Novex pharma
  • Roxane laboratories inc
  • Teva parenteral medicines inc
  • Watson laboratories inc
  • Wockhardt eu operations (swiss) ag
  • Amneal pharmaceuticals
  • Mova pharmaceuticals corp
  • Teva pharmaceuticals usa inc
  • Vintage pharmaceuticals llc
  • Vistapharm inc
  • Mylan pharmaceuticals inc
  • Muro pharmaceutical inc
  • Dava pharmaceuticals inc
  • American therapeutics inc
  • Mutual pharmaceutical co inc
  • Sandoz inc
  • Ucb inc
  • Warner chilcott div warner lambert co
  • Breath ltd
  • Sepracor inc
  • Teva Pharmaceuticals
Packagers
Dosage forms
FormRouteStrength
Aerosol, meteredRespiratory (inhalation)
LiquidOral
PowderRespiratory (inhalation)
SolutionIntramuscular
SolutionIntravenous
SolutionOral
SolutionRespiratory (inhalation)
TabletOral
Prices
Unit descriptionCostUnit
Xopenex 0.63 mg/3 ml solution64.2USDml
Proventil HFA 108 (90 Base)mcg/act Aerosol 6.7 gm Inhaler55.09USDinhaler
Xopenex HFA 45 mcg/act Aerosol 15 gm Inhaler53.84USDinhaler
AccuNeb 0.63 mg/3ml Neb. Solution 1 Box= 25 Vials53.14USDplastic
AccuNeb 1.25 mg/3ml Neb. Solution 1 Box= 25 Vials53.14USDplastic
ProAir HFA 108 (90 Base)mcg/act Aerosol 8.5 gm Inhaler45.99USDinhaler
Ventolin HFA 108 (90 Base)mcg/act Aerosol 18 gm Inhaler39.99USDinhaler
Proair hfa 90 mcg inhaler12.62USDg
Proventil hfa 90 mcg inhaler8.07USDg
Xopenex hfa 45 mcg inhaler6.12USDg
Xopenex 0.31 mg/3ml (1 Box = 24, 3ml Vials)4.87USDplastic
Xopenex 1.25 mg/3ml (1 Box = 24, 3ml Vials)4.87USDplastic
Xopenex 0.63 mg/3ml (1 Box = 24, 3ml Vials)4.71USDplastic
Xopenex 1.25 mg/3 ml solution2.96USDml
Ventolin hfa 90 mcg inhaler2.01USDg
Xopenex 0.31 mg/3 ml solution1.56USDml
Ventolin 5 mg/ml Solution1.13USDml
Ventolin Nebules P.F. 2 mg/ml Unit Dose Solution0.88USDml
Accuneb 0.63 mg/3 ml inh solution0.68USDml
Accuneb 1.25 mg/3 ml inh solution0.68USDml
Mylan-Salbutamol 5 mg/ml Solution0.62USDml
Pms-Salbutamol 5 mg/ml Solution0.62USDml
Ratio-Salbutamol 5 mg/ml Solution0.62USDml
Sandoz Salbutamol 5 mg/ml Solution0.62USDml
Mylan-Salbutamol Sterinebs P.F. 2 mg/ml Unit Dose Solution0.48USDml
Pms-Salbutamol Polyneb 2 mg/ml Unit Dose Solution0.48USDml
Ratio-Salbutamol Uni Dose P.F. 2 mg/ml Unit Dose Solution0.48USDml
Ventolin Nebules P.F. 1 mg/ml Solution0.47USDml
Mylan-Salbutamol Sterinebs P.F. 1 mg/ml Solution0.25USDml
Pms-Salbutamol 1 mg/ml Solution0.25USDml
Ratio-Salbutamol Sulf U.D.P.F. 1 mg/ml Solution0.25USDml
Apo-Salvent 4 mg Tablet0.22USDtablet
Pms-Salbutamol 0.5 mg/ml Solution0.16USDml
Ratio-Salbutamol Unit Dose P.F 0.5 mg/ml Solution0.16USDml
Apo-Salvent 2 mg Tablet0.13USDtablet
Pms-Salbutamol 400 mcg/ml Liquid0.05USDml
Ratio-Salbutamol Hfa 100 mcg/dose Metered Dose Aerosol0.04USDdose
Airomir Cfc-Free 100 mcg/dose Metered Dose Aerosol0.03USDdose
Apo-Salvent Cfc Free 100 mcg/dose Metered Dose Aerosol0.03USDdose
Ventolin Hfa 100 mcg/dose Metered Dose Aerosol0.03USDdose
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States75004442005-07-042025-07-04
United States63526841992-11-282009-11-28
Canada21256652001-06-122012-12-04
Canada21256672000-06-132012-12-04
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point147-149Lunts, L.H.C. and Toon, P.; U.S. Patent 3,644,353; February 22,1972; assigned to Allen & Hanburys Ltd.
water solubility1.41E+004 mg/LYALKOWSKY,SH & HE,Y (2003)
logP1.4Not Available
logS-1.22ADME Research, USCD
pKa10.3Not Available
Predicted Properties
PropertyValueSource
water solubility2.15e+00 g/lALOGPS
logP0.44ALOGPS
logP0.34ChemAxon
logS-2ALOGPS
pKa (strongest acidic)10.12ChemAxon
pKa (strongest basic)9.4ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count4ChemAxon
polar surface area72.72ChemAxon
rotatable bond count5ChemAxon
refractivity67.87ChemAxon
polarizability26.86ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Toshikuni Kawazi, Masahiro Ono, Nobuko Inoue, “Salbutamol-containing plaster and method of producing same.” U.S. Patent US5068103, issued February, 1984.

US5068103
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD02147
PubChem Compound2083
PubChem Substance46505312
ChemSpider1999
BindingDB25769
ChEBI2549
ChEMBLCHEMBL714
Therapeutic Targets DatabaseDNC000873
PharmGKBPA448068
IUPHAR558
Guide to Pharmacology558
Drug Product Database790419
RxListhttp://www.rxlist.com/cgi/generic/duoneb.htm
WikipediaSalbutamol
ATC CodesR03CC02R03AC02
AHFS Codes
  • 12:12.08.12
  • 48:12.04.12
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(52.5 KB)
Interactions
Drug Interactions
Drug
AmitriptylineThe tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of salbutamol.
AmoxapineThe tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of salbutamol.
AtenololAntagonism
BisoprololAntagonism
CarvedilolAntagonism
ClomipramineThe tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of salbutamol.
DesipramineThe tricyclic antidepressant, desipramine, increases the sympathomimetic effect of salbutamol.
DoxepinThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of salbutamol.
EsmololAntagonism
ImipramineThe tricyclic antidepressant, imipramine, increases the sympathomimetic effect of salbutamol.
IsocarboxazidIncreased arterial pressure
LabetalolAntagonism
LinezolidPossible increase of arterial pressure
MethyldopaIncreased arterial pressure
MetoprololAntagonism
MidodrineIncreased arterial pressure
MoclobemideMoclobemide increases the sympathomimetic effect of salbutamol.
NadololAntagonism
NortriptylineThe tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of salbutamol.
OxprenololAntagonism
PhenelzineIncreased arterial pressure
PindololAntagonism
PropranololAntagonism
RasagilineIncreased arterial pressure
ReserpineIncreased arterial pressure
TimololAntagonism
Food InteractionsNot Available

Targets

1. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

References:

  1. Brichetto L, Milanese M, Song P, Patrone M, Crimi E, Rehder K, Brusasco V: Beclomethasone rapidly ablates allergen-induced beta 2-adrenoceptor pathway dysfunction in human isolated bronchi. Am J Physiol Lung Cell Mol Physiol. 2003 Jan;284(1):L133-9. Epub 2002 Aug 16. Pubmed
  2. Chong LK, Suvarna K, Chess-Williams R, Peachell PT: Desensitization of beta2-adrenoceptor-mediated responses by short-acting beta2-adrenoceptor agonists in human lung mast cells. Br J Pharmacol. 2003 Feb;138(3):512-20. Pubmed
  3. Yamanishi T, Chapple CR, Yasuda K, Yoshida K, Chess-Williams R: Role of beta-adrenoceptor subtypes in mediating relaxation of the pig bladder trigonal muscle in vitro. Neurourol Urodyn. 2003;22(4):338-42. Pubmed
  4. Brouri F, Hanoun N, Mediani O, Saurini F, Hamon M, Vanhoutte PM, Lechat P: Blockade of beta 1- and desensitization of beta 2-adrenoceptors reduce isoprenaline-induced cardiac fibrosis. Eur J Pharmacol. 2004 Feb 6;485(1-3):227-34. Pubmed
  5. Choudhry S, Ung N, Avila PC, Ziv E, Nazario S, Casal J, Torres A, Gorman JD, Salari K, Rodriguez-Santana JR, Toscano M, Sylvia JS, Alioto M, Castro RA, Salazar M, Gomez I, Fagan JK, Salas J, Clark S, Lilly C, Matallana H, Selman M, Chapela R, Sheppard D, Weiss ST, Ford JG, Boushey HA, Drazen JM, Rodriguez-Cintron W, Silverman EK, Burchard EG: Pharmacogenetic differences in response to albuterol between Puerto Ricans and Mexicans with asthma. Am J Respir Crit Care Med. 2005 Mar 15;171(6):563-70. Epub 2004 Nov 19. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Beta-1 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

References:

  1. Baker JG: The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors. Br J Pharmacol. 2005 Feb;144(3):317-22. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12