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

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 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
Structure-activity relationship studies of (+/-)-terbutaline and (+/-)-fenoterol on beta3-adrenoceptors in the guinea pig gastric fundus.	2001 Aug	11885748
RANTES release by human airway smooth muscle: effects of prostaglandin E(2) and fenoterol.	2001 Dec 21	11755157
The predictive value of asthma medications to identify individuals with asthma--a study in German general practices.	2001 Nov	11761200
Effect of fenoterol-induced constitutive beta(2)-adrenoceptor activity on contractile receptor function in airway smooth muscle.	2001 Nov 23	11730729
[Drug prescription for hospitalized pediatric patients: how can the quality be evaluated?].	2001 Oct-Dec	11813049
Fenoterol-induced erythema exudativum multiforme-like exanthem: demonstration of drug-specific lymphocyte reactivity in vivo and in vitro.	2001 Oct-Nov	11800149
[Nitroglycerin patch for tocolysis--a prospective randomized comparison with fenoterol by infusion].	2001 Sep-Oct	11727665
[Pharmacodynamics of inhalation broncholytic agents introduced in a single dose by nebulizer in patients with severe exacerbation of bronchial asthma].	2002	11980113
Alfa 1 adrenergic potentiation of progesterone accumulation stimulated by vasoactive intestinal peptide (VIP) and pituitary adenylate cyclase-activating polypeptide (PACAP) in cultured rat granulosa cells.	2002 Apr	12011800
Airway responsiveness and airway remodeling after chronic exposure to procaterol and fenoterol in guinea pigs in vivo.	2002 Dec	12483037
Adverse effects of beta-agonists.	2002 Dec	12464943
Inhibition by fenoterol of human eosinophil functions including beta2-adrenoceptor-independent actions.	2002 Dec	12452831
Beta 2-agonist fenoterol has greater effects on contractile function of rat skeletal muscles than clenbuterol.	2002 Dec	12388476
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
[Anaphylactic shock following intravenous hydrocortisone succinate administration].	2002 Mar	11993080
In vitro sensitization of human bronchus by beta2-adrenergic agonists.	2002 Nov	12376356
Diagnostic evidence for the presence of beta-agonists using two consecutive derivatization procedures and gas chromatography-mass spectrometric analysis.	2002 Nov 15	12383481
The beta2- and beta3-adrenoceptor-mediated relaxation induced by fenoterol in guinea pig taenia caecum.	2002 Oct	12596892
Use of a novel cation-exchange restricted-access material for automated sample clean-up prior to the determination of basic drugs in plasma by liquid chromatography.	2002 Oct 25	12458755
[Continuous fenoterol inhalation by children with severe acute asthma: immediate clinical effects].	2002 Sep-Oct	14647750
[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
Maternal and fetal side effects of tocolysis using transdermal nitroglycerin or intravenous fenoterol combined with magnesium sulfate.	2003 Jan 10	12475575
[Side effects of fenoterol inhalation in asthmatic children].	2003 Jul-Aug	14513141
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
Supraventricular tachycardia after fenoterol inhalation: report of two cases.	2003 May-Jun	14521024
Science and physicianly practice: are they compatible?	2003 Nov	14678245
Spectrophotometric determination of fenoterol hydrobromide in pure form and dosage forms.	2003 Oct	14505735
Fenoterol delivery by Respimat soft mist inhaler versus CFC metered dose inhaler: cumulative dose-response study in asthma patients.	2003 Sep	14580004
Role of Src in hypersensitization to phosphodiesterase inhibitors in beta2-adrenoceptor-desensitized eosinophils.	2003 Sep	14571280
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 dopexamine in comparison with fenoterol on carbohydrate, fat and protein metabolism in healthy volunteers.	2004 Apr	14985966
Effect of Bryophyllum pinnatum versus fenoterol on uterine contractility.	2004 Apr 15	15063954
Clinical inquiries. Do inhaled beta-agonists control cough in URIs or acute bronchitis?	2004 Aug	15298845
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
Beta 2-agonist administration reverses muscle wasting and improves muscle function in aged rats.	2004 Feb 15	14617677
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	15337638
Modulation of beta2- and beta3-adrenoceptor-mediated relaxation of rat oesophagus smooth muscle by protein kinase C.	2004 Jul 8	15219823
[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
Improved delivery of ipratropium bromide/fenoterol from Respimat Soft Mist Inhaler in patients with COPD.	2004 May	15139567
Differential effects of beta2-adrenoceptor desensitization on the IgE-dependent release of chemical mediators from cultured human mast cells.	2004 Oct	15467193
Betamimetics for inhibiting preterm labour.	2004 Oct 18	15495104
Nociceptin inhibits vanilloid TRPV-1-mediated neurosensitization induced by fenoterol in human isolated bronchi.	2004 Sep	15351928
Altered beta2-adrenergic regulation of T cell activity after allergen challenge in asthma.	2004 Sep	15347367
Beta 2-agonist treatment enhances uterine oxytocin receptor mRNA expression in pregnant rats.	2004 Sep	15278905
N-coumaroyldopamine and N-caffeoyldopamine increase cAMP via beta 2-adrenoceptors in myelocytic U937 cells.	2005 Apr	15790999
Short-acting inhaled beta-2-agonists increased the mortality from chronic obstructive pulmonary disease in observational designs.	2005 Jan	15649676
Beta2-agonist administration increases sarcoplasmic reticulum Ca2+-ATPase activity in aged rat skeletal muscle.	2005 Mar	15479951

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 `Sat Dec 16 16:58:52 GMT 2023` Edited by `admin` on `Sat Dec 16 16:58:52 GMT 2023`
Record UNII	22M9P70OQ9
Record Status	`Validated (UNII)`
Record Version

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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