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targets (3)
for drugs
Identification
Name Fenoterol
Accession Number DB01288
Type small molecule
Groups approved
Description

An adrenergic beta-2 agonist that is used as a bronchodilator and tocolytic. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Fenoterolum [inn-latin]
  • Phenoterol
Brand names
  • Berotec
Brand name mixtures
  • Duovent UDV (Fenoterol Hydrobromide + Ipratropium Bromide)
Categories
  • Sympathomimetics
  • Bronchodilator Agents
  • Adrenergic beta-Agonists
  • Tocolytic Agents
CAS number 13392-18-2
Weight Average: 303.3529
Monoisotopic: 303.147058165
Chemical Formula C17H21NO4
InChI Key InChIKey=LSLYOANBFKQKPT-UHFFFAOYSA-N
InChI
InChI=1S/C17H21NO4/c1-11(6-12-2-4-14(19)5-3-12)18-10-17(22)13-7-15(20)9-16(21)8-13/h2-5,7-9,11,17-22H,6,10H2,1H3
Plain Text
IUPAC Name
5-(1-hydroxy-2-{[1-(4-hydroxyphenyl)propan-2-yl]amino}ethyl)benzene-1,3-diol
SMILES
CC(CC1=CC=C(O)C=C1)NCC(O)C1=CC(O)=CC(O)=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Amphetamines
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Benzene and Derivatives
  • Amino Alcohols
  • Phenethylamines
  • Aromatic compounds
  • Alcohols and Polyols
  • Phenyl Esters
  • Amphetamines
  • Resorcinols
Pharmacology
Indication Fenoterol is used for the treatment of asthma.
Pharmacodynamics Fenoterol is a beta agonist designed to open up the airways to the lungs by decreasing bronchconstriction.
Mechanism of action Beta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Hepatic.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Symptoms of overdose include angina (chest pain), dizziness, dry mouth, fatigue, flu-like symptoms, headache, heart irregularities, high or low blood pressure, high blood sugar, insomnia, muscle cramps, nausea, nervousness, rapid heartbeat, seizures, and tremor.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms
Form Route Strength
Aerosol, metered Respiratory (inhalation)
Aerosol, metered Respiratory (inhalation)
Solution Respiratory (inhalation)
Solution Respiratory (inhalation)
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 1.62e-01 g/l ALOGPS
logP 1.36 ALOGPS
logP 1.36 ChemAxon Molconvert
logS -3.27 ALOGPS
pKa 10.24 ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 5 ChemAxon Molconvert
polar surface area 92.95 ChemAxon Molconvert
rotatable bond count 6 ChemAxon Molconvert
refractivity 85.00 ChemAxon Molconvert
polarizability 31.75 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 3343 Link_out
PubChem Substance 46509099 Link_out
ChemSpider 3226 Link_out
BindingDB 50131281 Link_out
ChEBI 149226 Link_out
ChEMBL 149226 Link_out
Therapeutic Targets Database DAP000946 Link_out
PharmGKB PA10079 Link_out
Drug Product Database 541389 Link_out
Wikipedia http://en.wikipedia.org/wiki/Fenoterol Link_out
ATC Codes
  • R03CC04
  • G02CA03
  • R03AC04
AHFS Codes
  • 12:12.08.12
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Take without regard to meals.
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. de Vries B, Roffel AF, Zaagsma J, Meurs H: Effect of fenoterol-induced constitutive beta(2)-adrenoceptor activity on contractile receptor function in airway smooth muscle. Eur J Pharmacol. 2001 Nov 23;431(3):353-9. Pubmed
  2. Boterman M, Smits SR, Meurs H, Zaagsma J: Protein kinase C potentiates homologous desensitization of the beta2-adrenoceptor in bovine tracheal smooth muscle. Eur J Pharmacol. 2006 Jan 4;529(1-3):151-6. Epub 2005 Dec 1. Pubmed
  3. Marone G, Ambrosio G, Bonaduce D, Genovese A, Triggiani M, Condorelli M: Inhibition of IgE-mediated histamine release from human basophils and mast cells by fenoterol. Int Arch Allergy Appl Immunol. 1984;74(4):356-61. Pubmed
  4. Coqueret O, Demarquay D, Lagente V: Role of cyclic AMP in the modulation of IgE production by the beta 2-adrenoceptor agonist, fenoterol. Eur Respir J. 1996 Feb;9(2):220-5. Pubmed
  5. Bouillon T, Meineke I, Port R, Hildebrandt R, Gunther K, Gundert-Remy U: Concentration-effect relationship of the positive chronotropic and hypokalaemic effects of fenoterol in healthy women of childbearing age. Eur J Clin Pharmacol. 1996;51(2):153-60. 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. Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes—characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. Pubmed

3. Beta-3 adrenergic receptor

Pharmacological action: unknown
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis

Organism class: human
UniProt ID: P13945 Link_out
Gene: ADRB3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes—characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. Pubmed
Comments
Drug created on June 28, 2007 09:56 / Updated on April 19, 2011 15:09

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