FENOTEROL

Possibly Marketed Outside US

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

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

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 209 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24454993	Agonist 2752	193.0 nM [Kd]
Beta-1 adrenergic receptor 163 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 2752	13600.0 nM [Ki]
Beta-3 adrenergic receptor 54 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 2752	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 8583	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 8583	Unknown Approved Use Tocolysis with the aim to reduce premature labor and fetal mortality.

PubMed

Title	Date	PubMed
Exposure to TARC alters beta2-adrenergic receptor signaling in human peripheral blood T lymphocytes.	2005-07	15749741
Chronic beta-agonist administration affects cardiac function of adult but not old rats, independent of beta-adrenoceptor density.	2005-07	15734875
Self-limitation of intravenous tocolysis with beta2-adrenergic agonists is mediated through receptor G protein uncoupling.	2005-05	15728216
N-coumaroyldopamine and N-caffeoyldopamine increase cAMP via beta 2-adrenoceptors in myelocytic U937 cells.	2005-04	15790999
Beta2-agonist administration increases sarcoplasmic reticulum Ca2+-ATPase activity in aged rat skeletal muscle.	2005-03	15479951
Past, present and future--beta2-adrenoceptor agonists in asthma management.	2005-02	15715182
Short-acting inhaled beta-2-agonists increased the mortality from chronic obstructive pulmonary disease in observational designs.	2005-01	15649676
Respimat Soft Mist inhaler versus hydrofluoroalkane metered dose inhaler: patient preference and satisfaction.	2005	15725050
G-protein-coupled receptor chromatographic stationary phases. 2. Ligand-induced conformational mobility in an immobilized beta2-adrenergic receptor.	2004-12-15	15595859
Betamimetics for inhibiting preterm labour.	2004-10-18	15495104
Differential effects of beta2-adrenoceptor desensitization on the IgE-dependent release of chemical mediators from cultured human mast cells.	2004-10	15467193
Nociceptin inhibits vanilloid TRPV-1-mediated neurosensitization induced by fenoterol in human isolated bronchi.	2004-09	15351928
Altered beta2-adrenergic regulation of T cell activity after allergen challenge in asthma.	2004-09	15347367
Beta 2-agonist treatment enhances uterine oxytocin receptor mRNA expression in pregnant rats.	2004-09	15278905
Beneficial effects of chronic pharmacological manipulation of beta-adrenoreceptor subtype signaling in rodent dilated ischemic cardiomyopathy.	2004-08-31	15313944
Suboptimal management of subclinical hypothyroidism.	2004-08-16	15310268
Mechanisms of beta-receptor stimulation-induced improvement of acute lung injury and pulmonary edema.	2004-08	15312205
Adrenergic regulation of vascular smooth muscle tone in calf digital artery.	2004-08	15305854
Clinical inquiries. Do inhaled beta-agonists control cough in URIs or acute bronchitis?	2004-08	15298845
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.	2004-07-30	15337638
Modulation of beta2- and beta3-adrenoceptor-mediated relaxation of rat oesophagus smooth muscle by protein kinase C.	2004-07-08	15219823
Improved delivery of ipratropium bromide/fenoterol from Respimat Soft Mist Inhaler in patients with COPD.	2004-05	15139567
Atypical beta-adrenoceptor subtypes mediate relaxations of rabbit corpus cavernosum.	2004-05	14752060
Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol.	2004-04-21	15080615
Effect of Bryophyllum pinnatum versus fenoterol on uterine contractility.	2004-04-15	15063954
Effects of dopexamine in comparison with fenoterol on carbohydrate, fat and protein metabolism in healthy volunteers.	2004-04	14985966
Beta2-adrenoceptor agonist fenoterol enhances functional repair of regenerating rat skeletal muscle after injury.	2004-04	14607853
[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].	2004-03	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.	2004-03	14966821
The function profile of compressed-air and ultrasonic nebulizers.	2004-02-18	14964980
Beta 2-agonist administration reverses muscle wasting and improves muscle function in aged rats.	2004-02-15	14617677
Bench-to-bedside review: beta2-Agonists and the acute respiratory distress syndrome.	2004-02	14975042
Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells.	2004-02	14730417
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.	2004-01	14722251
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
Inhibition by reproterol of cAMP PDE in intact mastocytoma P-815 cells.	2004	15219266
[Effect of high doses of broncholytics on the state of cardiovascular system during treatment of sever exacerbation of bronchial asthma].	2004	15125428
[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	15106417
[Continuous fenoterol inhalation by children with severe acute asthma: immediate clinical effects].	2003-12-04	14647750
Science and physicianly practice: are they compatible?	2003-11	14678245
Supraventricular tachycardia after fenoterol inhalation: report of two cases.	2003-10-03	14521024
Spectrophotometric determination of fenoterol hydrobromide in pure form and dosage forms.	2003-10	14505735
Enhanced G(i) signaling selectively negates beta2-adrenergic receptor (AR)--but not beta1-AR-mediated positive inotropic effect in myocytes from failing rat hearts.	2003-09-30	12975249
[Side effects of fenoterol inhalation in asthmatic children].	2003-09-27	14513141
Fenoterol delivery by Respimat soft mist inhaler versus CFC metered dose inhaler: cumulative dose-response study in asthma patients.	2003-09	14580004
Role of Src in hypersensitization to phosphodiesterase inhibitors in beta2-adrenoceptor-desensitized eosinophils.	2003-09	14571280
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.	2003-09	12967929
Adverse effects of beta-agonists: are they clinically relevant?	2003	14719995
[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	14669617
Efficacy, safety, and acceptance of beclomethasone dipropionate administered via a new dry powder Inhaler or a standard CFC metered-dose inhaler in asthma patients.	2001-05-31	14512676

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:40:17 GMT 2025` Edited by `admin` on `Wed Apr 02 08:40:17 GMT 2025`
Record UNII	22M9P70OQ9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FENOTEROL

Official Name

English

FENOTEROL [MI]

Preferred 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

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