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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
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
AerolinNot Available
AiromirNot Available
AsmolNot Available
AsthalinNot Available
AsthaventNot Available
ProAirTeva
ProventilNot Available
SalamolNot Available
VentilanGlaxoSmithKline
VentolinGlaxoSmithKline
VentolineGlaxoSmithKline
VentorlinGlaxoSmithKline
Brand mixtures
Brand NameIngredients
CombiventIpratropium Bromide + Salbutamol Sulfate
Gen-Combo SterinebsIpratropium Bromide + Salbutamol Sulfate
Categories
CAS number18559-94-9
WeightAverage: 239.3107
Monoisotopic: 239.152143543
Chemical FormulaC13H21NO3
InChI KeyInChIKey=NDAUXUAQIAJITI-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
    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

    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

    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

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