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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
Salts Not Available
Brand names
Name Company
Berotec
Brand mixtures
Brand Name Ingredients
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
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 1.62e-01 g/l ALOGPS
logP 1.36 ALOGPS
logP 1.47 ChemAxon
logS -3.3 ALOGPS
pKa (strongest acidic) 8.85 ChemAxon
pKa (strongest basic) 9.63 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 5 ChemAxon
polar surface area 92.95 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 85 ChemAxon
polarizability 31.75 ChemAxon
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
IUPHAR 557 Link_out
Guide to Pharmacology 557 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
Drug Interaction
Acebutolol Antagonism
Alseroxylon Increased arterial pressure
Amitriptyline The tricyclic antidepressant, amitriptyline, may increase the sympathomimetic effect of fenoterol.
Amoxapine The tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of fenoterol.
Atenolol Antagonism
Betaxolol Beta-Blockers (Beta-1 Selective) like betaxolol may diminish the bronchodilatory effect of Beta2-Agonists like fenoterol. Therapy should be monitored.
Bevantolol Antagonism
Bisoprolol Antagonism
Carteolol Antagonism
Carvedilol Antagonism
Clomipramine The tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of fenoterol.
Deserpidine Increased arterial pressure
Desipramine The tricyclic antidepressant, desipramine, increases the sympathomimetic effect of fenoterol.
Doxepin The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of fenoterol.
Esmolol Antagonism
Imipramine The tricyclic antidepressant, imipramine, increases the sympathomimetic effect of fenoterol.
Isocarboxazid Increased arterial pressure
Labetalol Antagonism
Linezolid Possible increase of arterial pressure
Methyldopa Increased arterial pressure
Metoprolol Antagonism
Midodrine Increased arterial pressure
Moclobemide Moclobemide increases the sympathomimetic effect of fenoterol.
Nadolol Antagonism
Nortriptyline The tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of fenoterol.
Oxprenolol Antagonism
Pargyline Increased arterial pressure
Penbutolol Antagonism
Phenelzine Increased arterial pressure
Pindolol Antagonism
Practolol Antagonism
Propranolol Antagonism
Protriptyline The tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of fenoterol.
Rasagiline Increased arterial pressure
Reserpine Increased arterial pressure
Sotalol Antagonism
Timolol Antagonism
Tranylcypromine Increased arterial pressure
Trimipramine The tricyclic antidepressant, trimipramine, increases the sympathomimetic effect of fenoterol.
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 February 08, 2013 16:20