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Identification
Name Salbutamol
Accession Number DB01001 (APRD00553)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Albuterol
  • Albuterol Sulfate
  • Albuterol Sulphate
  • Levalbuterol
  • Salbutamol Sulfate
  • Salbutamol Sulphate
Brand names
  • Accuneb
  • Aerolin
  • Airomir
  • Asmaven
  • Asmol
  • Asthalin
  • Asthavent
  • Broncovaleas
  • Buventol
  • Cetsim
  • Cobutolin
  • Ecovent
  • Loftan
  • ProAir
  • ProAir HFA
  • Proventil
  • Proventil HFA
  • Rotahaler
  • Salamol
  • Salbulin
  • Salbutard
  • Salbutine
  • Salbuvent
  • Solbutamol
  • Sultanol
  • Venetlin
  • Ventalin Inhaler
  • Ventolin
  • Ventolin HFA
  • Ventolin Inhaler
  • Ventolin Rotacaps
  • Volma
  • Volmax
  • Xopenex
  • Xopenex HFA
Brand name mixtures
  • Combivent (Ipratropium Bromide + Salbutamol Sulfate)
  • Gen-Combo Sterinebs (Ipratropium Bromide + Salbutamol Sulfate)
Categories
  • Bronchodilator Agents
  • Adrenergic beta-Agonists
  • Tocolytic Agents
CAS number 18559-94-9
Weight Average: 239.3107
Monoisotopic: 239.152143543
Chemical Formula C13H21NO3
InChI Key InChIKey=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
Plain Text
IUPAC Name
4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
SMILES
CC(C)(C)NCC(O)C1=CC(CO)=C(O)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzyl Alcohols and Derivatives
  • Phenols and Derivatives
  • Phenethylamines
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Benzene and Derivatives
  • Alcohols and Polyols
  • Amino Alcohols
  • Phenethylamines
  • Aromatic compounds
  • Phenyl Esters
Pharmacology
Indication For symptomatic relief and prevention of bronchospasm due to bronchial asthma, chronic bronchitis, and other chronic bronchopulmonary disorders such as COPD.
Pharmacodynamics Salbutamol (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 action Salbutamol 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.
Absorption Systemic absorption is rapid following aerosol administration.
Volume of distribution Not Available
Protein binding Not 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.
Route of elimination Approximately 72% of the inhaled dose is excreted in the urine within 24 hours, 28% as unchanged drug and 44% as metabolite.
Half life 1.6 hours
Clearance Not Available
Toxicity LD50=1100 mg/kg (orally in mice)
Affected organisms
  • Humans and other mammals
Pathways Not Available
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
Form Route Strength
Aerosol, metered Respiratory (inhalation)
Liquid Oral
Powder Respiratory (inhalation)
Solution Intramuscular
Solution Intravenous
Solution Oral
Solution Respiratory (inhalation)
Tablet Oral
Prices
Unit description Cost Unit
Xopenex 0.63 mg/3 ml solution 64.2 USD ml
Proventil HFA 108 (90 Base)mcg/act Aerosol 6.7 gm Inhaler 55.09 USD inhaler
Xopenex HFA 45 mcg/act Aerosol 15 gm Inhaler 53.84 USD inhaler
AccuNeb 0.63 mg/3ml Neb. Solution 1 Box= 25 Vials 53.14 USD plastic
AccuNeb 1.25 mg/3ml Neb. Solution 1 Box= 25 Vials 53.14 USD plastic
ProAir HFA 108 (90 Base)mcg/act Aerosol 8.5 gm Inhaler 45.99 USD inhaler
Ventolin HFA 108 (90 Base)mcg/act Aerosol 18 gm Inhaler 39.99 USD inhaler
Proair hfa 90 mcg inhaler 12.62 USD g
Proventil hfa 90 mcg inhaler 8.07 USD g
Xopenex hfa 45 mcg inhaler 6.12 USD g
Xopenex 0.31 mg/3ml (1 Box = 24, 3ml Vials) 4.87 USD plastic
Xopenex 1.25 mg/3ml (1 Box = 24, 3ml Vials) 4.87 USD plastic
Xopenex 0.63 mg/3ml (1 Box = 24, 3ml Vials) 4.71 USD plastic
Xopenex 1.25 mg/3 ml solution 2.96 USD ml
Ventolin hfa 90 mcg inhaler 2.01 USD g
Xopenex 0.31 mg/3 ml solution 1.56 USD ml
Ventolin 5 mg/ml Solution 1.13 USD ml
Ventolin Nebules P.F. 2 mg/ml Unit Dose Solution 0.88 USD ml
Accuneb 0.63 mg/3 ml inh solution 0.68 USD ml
Accuneb 1.25 mg/3 ml inh solution 0.68 USD ml
Mylan-Salbutamol 5 mg/ml Solution 0.62 USD ml
Pms-Salbutamol 5 mg/ml Solution 0.62 USD ml
Ratio-Salbutamol 5 mg/ml Solution 0.62 USD ml
Sandoz Salbutamol 5 mg/ml Solution 0.62 USD ml
Mylan-Salbutamol Sterinebs P.F. 2 mg/ml Unit Dose Solution 0.48 USD ml
Pms-Salbutamol Polyneb 2 mg/ml Unit Dose Solution 0.48 USD ml
Ratio-Salbutamol Uni Dose P.F. 2 mg/ml Unit Dose Solution 0.48 USD ml
Ventolin Nebules P.F. 1 mg/ml Solution 0.47 USD ml
Mylan-Salbutamol Sterinebs P.F. 1 mg/ml Solution 0.25 USD ml
Pms-Salbutamol 1 mg/ml Solution 0.25 USD ml
Ratio-Salbutamol Sulf U.D.P.F. 1 mg/ml Solution 0.25 USD ml
Apo-Salvent 4 mg Tablet 0.22 USD tablet
Pms-Salbutamol 0.5 mg/ml Solution 0.16 USD ml
Ratio-Salbutamol Unit Dose P.F 0.5 mg/ml Solution 0.16 USD ml
Apo-Salvent 2 mg Tablet 0.13 USD tablet
Pms-Salbutamol 400 mcg/ml Liquid 0.05 USD ml
Ratio-Salbutamol Hfa 100 mcg/dose Metered Dose Aerosol 0.04 USD dose
Airomir Cfc-Free 100 mcg/dose Metered Dose Aerosol 0.03 USD dose
Apo-Salvent Cfc Free 100 mcg/dose Metered Dose Aerosol 0.03 USD dose
Ventolin Hfa 100 mcg/dose Metered Dose Aerosol 0.03 USD dose
Patents
Country Patent Number Approved Expires
United States 7500444 2005-07-04 2025-07-04
United States 6352684 1992-11-28 2009-11-28
Canada 2125665 2001-06-12 2012-12-04
Canada 2125667 2000-06-13 2012-12-04
Properties
State solid
Melting point 157-158oC
Experimental Properties
Property Value Source
water solubility 3 mg/L PhysProp
logP 1.4 PhysProp
logS -1.22 [ADME Research, USCD] PhysProp
pKa 10.3 Various sources
Predicted Properties
Property Value Source
water solubility 2.15e+00 g/l ALOGPS
logP 0.44 ALOGPS
logP 0.32 ChemAxon Molconvert
logS -2.05 ALOGPS
pKa 14.18 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 72.72 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 67.87 ChemAxon Molconvert
polarizability 26.95 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D02147 Link_out
PubChem Compound 2083 Link_out
PubChem Substance 46505312 Link_out
ChemSpider 1999 Link_out
BindingDB 25769 Link_out
ChEBI 2549 Link_out
ChEMBL 2549 Link_out
Therapeutic Targets Database DNC000873 Link_out
PharmGKB PA448068 Link_out
Drug Product Database 790419 Link_out
RxList http://www.rxlist.com/cgi/generic/duoneb.htm Link_out
Wikipedia http://en.wikipedia.org/wiki/Salbutamol Link_out
ATC Codes
  • R03CC02
  • R03AC02
AHFS Codes
  • 12:12.08.12
  • 48:12.04.12
PDB Entries Not Available
FDA label Not Available
MSDS show (52.5 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Beta-2 adrenergic receptor

Pharmacological action: yes
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 November 10, 2010 13:45

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.