Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H21NO4 |
| Molecular Weight | 303.3529 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H](CC1=CC=C(O)C=C1)NC[C@H](O)C2=CC(O)=CC(O)=C2
InChI
InChIKey=LSLYOANBFKQKPT-DIFFPNOSSA-N
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/t11-,17+/m1/s1
| Molecular Formula | C17H21NO4 |
| Molecular Weight | 303.3529 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3466.1999.tb00006.x/pdf
https://www.ncbi.nlm.nih.gov/pubmed/7613161
Curator's Comment: description was created based on several sources, including
http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3466.1999.tb00006.x/pdf
https://www.ncbi.nlm.nih.gov/pubmed/7613161
Fenoterol is a beta2-adrenoreceptor agonist, used as a bronchodilator for the treatment and prevention of bronchospasms, associated with asthma and chronic obstructive airway disease, including bronchitis and pulmonary emphysema. Fenoterol is also used for tocolysis during premature labor. Marketing of fenoterol for treatment of asthma was suspended in Australia and New Zealand because of an increased risk of deaths, most likely due to excessive self-administration of the drug.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL210 |
193.0 nM [Kd] | ||
Target ID: P08588 Gene ID: 153.0 Gene Symbol: ADRB1 Target Organism: Homo sapiens (Human) |
13600.0 nM [Ki] | ||
Target ID: P13945 Gene ID: 155.0 Gene Symbol: ADRB3 Target Organism: Homo sapiens (Human) |
55700.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | BEROTEC Approved UseFenoterol is indicated as bronchodilator for the treatment of bronchospasm associated with asthma, and for prevention bronchospasm and reduce the frequency of acute asthma exacerbations in patients with chronic asthma, who require regular treatment with an inhaled shorter-acting beta-adrenergic bronchodilator. Fenoterol is indicated as bronchodilators for the treatment of bronchospasm associated with chronic obstructive airway disease, including bronchitis and pulmonary emphysema. |
|||
| Primary | Unknown Approved UseTocolysis with the aim to reduce premature labor and fetal mortality. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Continuous fenoterol inhalation by children with severe acute asthma: immediate clinical effects]. | 2002 Sep-Oct |
|
| Adverse effects of beta-agonists: are they clinically relevant? | 2003 |
|
| [The test for nitric oxide metabolites in exhaled air condensate as a method of assessing NO-reactivity of the airways in patients with bronchial asthma]. | 2003 |
|
| [Side effects of fenoterol inhalation in asthmatic children]. | 2003 Jul-Aug |
|
| Efficacy, safety, and acceptance of beclomethasone dipropionate administered via a new dry powder Inhaler or a standard CFC metered-dose inhaler in asthma patients. | 2003 Jul-Aug |
|
| [Cerebral hemorrhage and periventricular leucomalacia in preterm neonates after intravenous tocolysis with fenoterol: results of postnatal ultrasound examination]. | 2003 Mar-Apr |
|
| Supraventricular tachycardia after fenoterol inhalation: report of two cases. | 2003 May-Jun |
|
| Science and physicianly practice: are they compatible? | 2003 Nov |
|
| Fenoterol delivery by Respimat soft mist inhaler versus CFC metered dose inhaler: cumulative dose-response study in asthma patients. | 2003 Sep |
|
| Role of Src in hypersensitization to phosphodiesterase inhibitors in beta2-adrenoceptor-desensitized eosinophils. | 2003 Sep |
|
| Atypical beta-adrenoceptors, different from beta 3-adrenoceptors and probably from the low-affinity state of beta 1-adrenoceptors, relax the rat isolated mesenteric artery. | 2003 Sep |
|
| Enhanced G(i) signaling selectively negates beta2-adrenergic receptor (AR)--but not beta1-AR-mediated positive inotropic effect in myocytes from failing rat hearts. | 2003 Sep 30 |
|
| The function profile of compressed-air and ultrasonic nebulizers. | 2003 Sep-Oct |
|
| A review of ipratropium bromide/fenoterol hydrobromide (Berodual) delivered via Respimat Soft Mist Inhaler in patients with asthma and chronic obstructive pulmonary disease. | 2004 |
|
| Inhibition by reproterol of cAMP PDE in intact mastocytoma P-815 cells. | 2004 |
|
| [Effect of high doses of broncholytics on the state of cardiovascular system during treatment of sever exacerbation of bronchial asthma]. | 2004 |
|
| [Effects of nebuliser treatment with berotec on external respiratory function, bronchial permeability, hemodynamics, acid-alkaline balance, oxygen saturation, and their circadian structure in elderly patients with chronic obstructive pulmonary disease]. | 2004 |
|
| Effects of dopexamine in comparison with fenoterol on carbohydrate, fat and protein metabolism in healthy volunteers. | 2004 Apr |
|
| Beta2-adrenoceptor agonist fenoterol enhances functional repair of regenerating rat skeletal muscle after injury. | 2004 Apr |
|
| Effect of Bryophyllum pinnatum versus fenoterol on uterine contractility. | 2004 Apr 15 |
|
| Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol. | 2004 Apr 21 |
|
| Mechanisms of beta-receptor stimulation-induced improvement of acute lung injury and pulmonary edema. | 2004 Aug |
|
| Adrenergic regulation of vascular smooth muscle tone in calf digital artery. | 2004 Aug |
|
| Clinical inquiries. Do inhaled beta-agonists control cough in URIs or acute bronchitis? | 2004 Aug |
|
| Suboptimal management of subclinical hypothyroidism. | 2004 Aug 16 |
|
| Beneficial effects of chronic pharmacological manipulation of beta-adrenoreceptor subtype signaling in rodent dilated ischemic cardiomyopathy. | 2004 Aug 31 |
|
| G-protein-coupled receptor chromatographic stationary phases. 2. Ligand-induced conformational mobility in an immobilized beta2-adrenergic receptor. | 2004 Dec 15 |
|
| Bench-to-bedside review: beta2-Agonists and the acute respiratory distress syndrome. | 2004 Feb |
|
| Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. | 2004 Feb |
|
| Beta 2-agonist administration reverses muscle wasting and improves muscle function in aged rats. | 2004 Feb 15 |
|
| Characterization of agonist stimulation of cAMP-dependent protein kinase and G protein-coupled receptor kinase phosphorylation of the beta2-adrenergic receptor using phosphoserine-specific antibodies. | 2004 Jan |
|
| Different mechanisms of action of beta2-adrenergic receptor agonists: a comparison of reproterol, fenoterol and salbutamol on monocyte cyclic-AMP and leukotriene B4 production in vitro. | 2004 Jul 30 |
|
| Modulation of beta2- and beta3-adrenoceptor-mediated relaxation of rat oesophagus smooth muscle by protein kinase C. | 2004 Jul 8 |
|
| [Comparison of the cost of treatment of premature labor with atosiban or beta-sympathomimetics from the perspective of the health care payer--a pharmacoeconomic model]. | 2004 Mar |
|
| Efficacy and safety of ipratropium bromide plus fenoterol inhaled via Respimat Soft Mist Inhaler vs. a conventional metered dose inhaler plus spacer in children with asthma. | 2004 Mar |
|
| Improved delivery of ipratropium bromide/fenoterol from Respimat Soft Mist Inhaler in patients with COPD. | 2004 May |
|
| Atypical beta-adrenoceptor subtypes mediate relaxations of rabbit corpus cavernosum. | 2004 May |
|
| Differential effects of beta2-adrenoceptor desensitization on the IgE-dependent release of chemical mediators from cultured human mast cells. | 2004 Oct |
|
| Betamimetics for inhibiting preterm labour. | 2004 Oct 18 |
|
| Nociceptin inhibits vanilloid TRPV-1-mediated neurosensitization induced by fenoterol in human isolated bronchi. | 2004 Sep |
|
| Altered beta2-adrenergic regulation of T cell activity after allergen challenge in asthma. | 2004 Sep |
|
| Beta 2-agonist treatment enhances uterine oxytocin receptor mRNA expression in pregnant rats. | 2004 Sep |
|
| Respimat Soft Mist inhaler versus hydrofluoroalkane metered dose inhaler: patient preference and satisfaction. | 2005 |
|
| N-coumaroyldopamine and N-caffeoyldopamine increase cAMP via beta 2-adrenoceptors in myelocytic U937 cells. | 2005 Apr |
|
| Past, present and future--beta2-adrenoceptor agonists in asthma management. | 2005 Feb |
|
| Short-acting inhaled beta-2-agonists increased the mortality from chronic obstructive pulmonary disease in observational designs. | 2005 Jan |
|
| Exposure to TARC alters beta2-adrenergic receptor signaling in human peripheral blood T lymphocytes. | 2005 Jul |
|
| Chronic beta-agonist administration affects cardiac function of adult but not old rats, independent of beta-adrenoceptor density. | 2005 Jul |
|
| Beta2-agonist administration increases sarcoplasmic reticulum Ca2+-ATPase activity in aged rat skeletal muscle. | 2005 Mar |
|
| Self-limitation of intravenous tocolysis with beta2-adrenergic agonists is mediated through receptor G protein uncoupling. | 2005 May |
Sample Use Guides
Fenoterol was available as inhalation aerosol and inhalation solution. As a bronchodilator aerosol in adults, 2 inhalations (100 or 200 mcg), three to four times a day, if necessary, but not to be administered more often than every four hours. Dosage should not exceed 8 inhalations of the 100 mcg per metered spray formulation or 6 inhalations of the 200 mcg per metered spray formulation per day. As an aid for prematue labor, fenoterol was used by i.v. infusion or p.o.
Route of Administration:
Other
Ability of fenoterol to activate beta2 adrenergic receptors was tested in beta2 receptors expressed in CHO cells using Adenylyl cyclase activity assay. 50 ug membrane protein was incubated with a buffer solution in the presence of 32P-ATP and test compound, and accumulation of 32P-cAMP was determined by beta-counter. Fenoterol activates beta2 receptor with Emax of 76% relative to isoproterenol.
| Substance Class |
Chemical
Created
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| Record UNII |
5Z64M7W0JM
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| Record Status |
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RACEMATE -> ACTIVE ENANTIOMER |
IN-VITRO
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