FENOTEROL

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H21NO4
Molecular Weight	303.3529
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.drugs.com/mmx/fenoterol-hydrobromide.html
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24454993	Agonist 2678	193.0 nM [Kd]
Beta-1 adrenergic receptor 158 Target ID: P08588 Gene ID: 153.0 Gene Symbol: ADRB1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14730417	Agonist 2678	13600.0 nM [Ki]
Beta-3 adrenergic receptor 49 Target ID: P13945 Gene ID: 155.0 Gene Symbol: ADRB3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14730417	Agonist 2678	55700.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bronchial spasm 78 Sources: https://www.drugs.com/mmx/fenoterol-hydrobromide.html	Primary		Approved 8429	BEROTEC Approved Use Fenoterol 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.
Premature labour 10 Sources: http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3466.1999.tb00006.x/pdf	Primary		Approved 8429	Unknown Approved Use Tocolysis with the aim to reduce premature labor and fetal mortality.

PubMed

Title	Date	PubMed
Bronchodilators for the prevention and treatment of chronic lung disease in preterm infants.	2001	11687053
[Significance of bronchospasm in the development of bronchial obstruction in exogenous allergic alveolitis].	2001	11508233
Inhaled short-acting beta2-agonists versus ipratropium for acute exacerbations of chronic obstructive pulmonary disease.	2001	11406052
Structure-activity relationship studies of (+/-)-terbutaline and (+/-)-fenoterol on beta3-adrenoceptors in the guinea pig gastric fundus.	2001 Aug	11885748
Systemic and topical drug administration in the pig ureter: effect of phosphodiesterase inhibitors alpha1, beta and beta2-adrenergic receptor agonists and antagonists on the frequency and amplitude of ureteral contractions.	2001 Aug	11458123
Sonographic cervical volumetry in higher order multiple gestation.	2001 Nov-Dec	11694737
[Comparison of acute bronchiolytic effect of inhaling solutions of berodual vs salgim using a nebulizer in patients with chronic obstructive bronchitis and bronchial asthma].	2002	12360595
[Inducible nitric oxide synthase in rat lungs in experimental bronchial asthma and its status in administering drugs with adrenergic action].	2002	12053770
Inhibition by fenoterol of human eosinophil functions including beta2-adrenoceptor-independent actions.	2002 Dec	12452831
SR 142801, a tachykinin NK(3) receptor antagonist, prevents beta(2)-adrenoceptor agonist-induced hyperresponsiveness to neurokinin A in guinea-pig isolated trachea.	2002 Dec 6	12427489
A comparison of terbutaline and fenoterol unit dose vials in treating children with acute asthmatic attacks.	2002 Jul-Aug	12238905
Determination of fenoterol in human plasma by HPLC with fluorescence detection after derivatization.	2002 Jun 20	12062673
Adverse effects of beta-agonists: are they clinically relevant?	2003	14719995
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	14512676
Spectrophotometric determination of fenoterol hydrobromide in pure form and dosage forms.	2003 Oct	14505735
Role of Src in hypersensitization to phosphodiesterase inhibitors in beta2-adrenoceptor-desensitized eosinophils.	2003 Sep	14571280
The function profile of compressed-air and ultrasonic nebulizers.	2003 Sep-Oct	14964980
A review of ipratropium bromide/fenoterol hydrobromide (Berodual) delivered via Respimat Soft Mist Inhaler in patients with asthma and chronic obstructive pulmonary disease.	2004	15257628
Effects of dopexamine in comparison with fenoterol on carbohydrate, fat and protein metabolism in healthy volunteers.	2004 Apr	14985966
Beta2-adrenoceptor agonist fenoterol enhances functional repair of regenerating rat skeletal muscle after injury.	2004 Apr	14607853
Effect of Bryophyllum pinnatum versus fenoterol on uterine contractility.	2004 Apr 15	15063954
Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol.	2004 Apr 21	15080615
Suboptimal management of subclinical hypothyroidism.	2004 Aug 16	15310268
Beneficial effects of chronic pharmacological manipulation of beta-adrenoreceptor subtype signaling in rodent dilated ischemic cardiomyopathy.	2004 Aug 31	15313944
G-protein-coupled receptor chromatographic stationary phases. 2. Ligand-induced conformational mobility in an immobilized beta2-adrenergic receptor.	2004 Dec 15	15595859
[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	15141520
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	14966821
Improved delivery of ipratropium bromide/fenoterol from Respimat Soft Mist Inhaler in patients with COPD.	2004 May	15139567
Atypical beta-adrenoceptor subtypes mediate relaxations of rabbit corpus cavernosum.	2004 May	14752060
N-coumaroyldopamine and N-caffeoyldopamine increase cAMP via beta 2-adrenoceptors in myelocytic U937 cells.	2005 Apr	15790999
Past, present and future--beta2-adrenoceptor agonists in asthma management.	2005 Feb	15715182
Exposure to TARC alters beta2-adrenergic receptor signaling in human peripheral blood T lymphocytes.	2005 Jul	15749741
Chronic beta-agonist administration affects cardiac function of adult but not old rats, independent of beta-adrenoceptor density.	2005 Jul	15734875
Self-limitation of intravenous tocolysis with beta2-adrenergic agonists is mediated through receptor G protein uncoupling.	2005 May	15728216

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Name

Type

Language

FENOTEROL

Official Name

English

FENOTEROL [MART.]

Common Name

English

FENOTEROL [VANDF]

Common Name

English

FENOTEROL HYDROBROMIDE IMPURITY A [EP IMPURITY]

Common Name

English

3,5-DIHYDROXY-.ALPHA.-(((P-HYDROXY-.ALPHA.-METHYLPHENETHYL)AMINO)METHYL)BENZYL ALCOHOL

Common Name

English

FENOTEROL [USAN]

Common Name

English

(1RS)-1-(3,5-DIHYDROXYPHENYL)-2-(((1RS)-2-(4-HYDROXYPHENYL)-1-METHYLETHYL)AMINO)ETHANOL

Systematic Name

English

1,3-BENZENEDIOL, 5-((1R)-1-HYDROXY-2-(((1R)-2-(4-HYDROXYPHENYL)-1-METHYLETHYL)AMINO)ETHYL)-, REL-

Systematic Name

English

1,3-BENZENEDIOL, 5-(1-HYDROXY-2-((2-(4-HYDROXYPHENYL)-1-METHYLETHYL)AMINO)ETHYL)-, (R*,R*)-(±)-

Systematic Name

English

FENOTEROL [MI]

Common Name

English

TH-1165

Code

English

fenoterol [INN]

Common Name

English

5-[(1RS)-2-[(1SR)-2-(4-hydroxyphenyl)-1-methylethyl]amino-1-hydroxyethyl]benzene-1,3-diol

Systematic Name

English

Fenoterol [WHO-DD]

Common Name

English

NSC-757811

Code

English

1,3-BENZENEDIOL, 5-(1-HYDROXY-2-((2-(4-HYDROXYPHENYL)-1-METHYLETHYL)AMINO)ETHYL)-

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

R03AL01