Fenoterol

Synonyms :
1-(3,5-Dihydroxyphenyl)-1-hydroxy-2-((4-hydroxyphenyl)isopropylamino)ethane, 1-(P-Hydroxyphenyl)-2-((beta-hydroxy-beta-(3′,5′-dihydroxyphenyl))ethyl)aminopropane, 3,5-Dihydroxy-alpha-(((P-hydroxy-alpha-methylphenethyl)amino)methyl)benzyl alcohol, 5-{1-hydroxy-2-[2-(4-hydroxy-phenyl)-1-methyl-ethylamino]-ethyl}-benzene-1,3-diol, Fenoterolum, Phenoterol

Status : approved

Category

Sympathomimetics

Therapeutic Classification

OTHER GYNECOLOGICALS

GENITO URINARY SYSTEM AND SEX HORMONES
OTHER GYNECOLOGICALS
OTHER GYNECOLOGICALS
Adrenergic beta-2 Receptor Agonists

Description

An adrenergic beta-2 agonist that is used as a bronchodilator and tocolytic. [PubChem]

Used

Fenoterol is used for the treatment of asthma.

Mechanism Of Action

Beta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.

Dosage

Form Route Strength
Solution inhalation 1 mg
Metered-dose aerosol inhalation; oral 100 mcg
Metered-dose aerosol inhalation; oral 0.2 mg
Tablet oral 2.5 mg
Solution inhalation; oral 0.25 mg
Solution inhalation; oral 0.625 mg
Solution inhalation; oral 0.125 mg

Pharmacodynamics

Fenoterol is a beta agonist designed to open up the airways to the lungs by decreasing bronchconstriction.

Toxic Effect

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.

Metabolism

Hepatic.

Chemical Classification

This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.

Amphetamines and derivatives

Organic compounds

Benzenoids

Benzene and substituted derivatives

Phenethylamines

Salt : Fenoterol hydrobromide

Chemical Name

1-(3,5-Dihydroxyphenyl)-1-hydroxy-2-((4-hydroxyphenyl)isopropylamino)ethane

Brands

name Dosage form Country
Berotec 1mg/ml solution Canada
Berotec Aem 100mcg/dose metered-dose aerosol Canada
Berotec Forte Metered Aer metered-dose aerosol Canada
Berotec Tab 2.5mg tablet Canada
Berotec Udv Inhalation Solution 0.25mg/ml solution Canada
Berotec Udv Inhalation Soluton 0.625mg/ml solution Canada
Duovent Udv solution Canada

Drug Drug Interactions

  •  Acebutolol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Aclidinium  : May enhance the anticholinergic effect of Anticholinergic Agents.
  •  Aminophylline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Amphetamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Arformoterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  armodafinil  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Articaine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Atomoxetine  : May enhance the tachycardic effect of Beta2-Agonists.
  •  Atomoxetine  : May enhance the hypertensive effect of Sympathomimetics. Atomoxetine may enhance the tachycardic effect of Sympathomimetics.
  •  Atosiban  : Beta2-Agonists may enhance the adverse/toxic effect of Atosiban. Specifically, there may be an increased risk for pulmonary edema and/or dyspnea.
  •  Benzphetamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Betahistine  : May diminish the therapeutic effect of Beta2-Agonists.
  •  Botulinum Toxin Type A  : Anticholinergic Agents may enhance the anticholinergic effect of AbobotulinumtoxinA.
  •  Botulinum Toxin Type A  : Anticholinergic Agents may enhance the anticholinergic effect of OnabotulinumtoxinA.
  •  Botulinum Toxin Type B  : Anticholinergic Agents may enhance the anticholinergic effect of RimabotulinumtoxinB.
  •  Butalbital  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Caffeine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Chlorphentermine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Clenbuterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Cocaine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Dexmethylphenidate  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Dextroamphetamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Diethylpropion  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Dihydrocodeine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Dipivefrin  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Dobutamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Dopamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Doxapram  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Dronabinol  : Cannabinoid-Containing Products may enhance the tachycardic effect of Sympathomimetics.
  •  Dyphylline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Ephedrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Epinephrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Formoterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Glucagon recombinant  : Anticholinergic Agents may enhance the adverse/toxic effect of Glucagon. Specifically, the risk of gastrointestinal adverse effects may be increased.
  •  Indacaterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Iobenguane  : May diminish the therapeutic effect of Iobenguane I 123.
  •  Isometheptene  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Isoprenaline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Itopride  : Anticholinergic Agents may diminish the therapeutic effect of Itopride.
  •  Labetalol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Levonordefrin  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Linezolid  : May enhance the hypertensive effect of Sympathomimetics.
  •  Lisdexamfetamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Loxapine  : Agents to Treat Airway Disease may enhance the adverse/toxic effect of Loxapine. More specifically, the use of Agents to Treat Airway Disease is likely a marker of patients who are likely at a greater risk for experiencing significant bronchospasm from use of inhaled loxapine.
  •  Mephentermine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Metaraminol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Methamphetamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Methoxamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Methylphenidate  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Mianserin  : May enhance the anticholinergic effect of Anticholinergic Agents.
  •  Midodrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Mirabegron  : Anticholinergic Agents may enhance the adverse/toxic effect of Mirabegron.
  •  Modafinil  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Nabilone  : Cannabinoid-Containing Products may enhance the tachycardic effect of Sympathomimetics.
  •  Naphazoline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Norepinephrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Olodaterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Orciprenaline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Oxymetazoline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Phendimetrazine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Pheniramine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Phenmetrazine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Phentermine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Phenylephrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Phenylpropanolamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Pirbuterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Potassium Chloride  : Anticholinergic Agents may enhance the ulcerogenic effect of Potassium Chloride.
  •  Pramlintide  : May enhance the anticholinergic effect of Anticholinergic Agents. These effects are specific to the GI tract.
  •  Propylhexedrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Pseudoephedrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Ritodrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Salbutamol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Salmeterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Secretin  : Anticholinergic Agents may diminish the therapeutic effect of Secretin.
  •  Sulpiride  : Anticholinergic Agents may diminish the therapeutic effect of LevoSulpiride.
  •  Tedizolid Phosphate  : May enhance the hypertensive effect of Sympathomimetics. Tedizolid may enhance the tachycardic effect of Sympathomimetics.
  •  Terbutaline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Theophylline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Tiotropium  : Anticholinergic Agents may enhance the anticholinergic effect of Tiotropium.
  •  Topiramate  : Anticholinergic Agents may enhance the adverse/toxic effect of Topiramate.
  •  Triprolidine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Umeclidinium  : May enhance the anticholinergic effect of Anticholinergic Agents.
  •  Vilanterol  : May enhance the adverse/toxic effect of other Sympathomimetics.

Food Interactions

  • Take without regard to meals.

Calculated Property

kind Value Source
logP 1.36 ALOGPS
logS -3.3 ALOGPS
Water Solubility 1.62e-01 g/l ALOGPS
logP 1.47 ChemAxon
IUPAC Name 5-(1-hydroxy-2-{[1-(4-hydroxyphenyl)propan-2-yl]amino}ethyl)benzene-1,3-diol ChemAxon
Traditional IUPAC Name fenoterol ChemAxon
Molecular Weight 303.3529 ChemAxon
Monoisotopic Weight 303.147058165 ChemAxon
SMILES CC(CC1=CC=C(O)C=C1)NCC(O)C1=CC(O)=CC(O)=C1 ChemAxon
Molecular Formula C17H21NO4 ChemAxon
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 ChemAxon
InChIKey InChIKey=LSLYOANBFKQKPT-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 92.95 ChemAxon
Refractivity 85 ChemAxon
Polarizability 31.75 ChemAxon
Rotatable Bond Count 6 ChemAxon
H Bond Acceptor Count 5 ChemAxon
H Bond Donor Count 5 ChemAxon
pKa (strongest acidic) 8.85 ChemAxon
pKa (strongest basic) 9.63 ChemAxon
Physiological Charge 1 ChemAxon
Number of Rings 2 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Beta-2 adrenergic receptor : in Human
  • Beta-1 adrenergic receptor : in Human
  • Beta-3 adrenergic receptor : in Human