FENOTEROL

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H21NO4
Molecular Weight	303.3536
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]([H])(Cc1ccc(cc1)O)NC[C@@]([H])(c2cc(cc(c2)O)O)O

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	303.3536
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 194 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24454993	Agonist 2470	193.0 nM [Kd]
Beta-1 adrenergic receptor 153 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 2470	13600.0 nM [Ki]
Beta-3 adrenergic receptor 46 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 2470	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 8043	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 11 Sources: http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3466.1999.tb00006.x/pdf	Primary		Approved 8043	Unknown Approved Use Tocolysis with the aim to reduce premature labor and fetal mortality.

PubMed

Title	Date	PubMed
[NO synthase activity in epitheliocytes of the rat bronchi following inhalation administration of adrenergic agonists and guanosine triphosphate].	2001	11548639
Inhaled short-acting beta2-agonists versus ipratropium for acute exacerbations of chronic obstructive pulmonary disease.	2001	11406052
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
Effects of fenoterol on beta-adrenoceptor and muscarinic M2 receptor function in bovine tracheal smooth muscle.	2001 May 11	11426849
The predictive value of asthma medications to identify individuals with asthma--a study in German general practices.	2001 Nov	11761200
Sonographic cervical volumetry in higher order multiple gestation.	2001 Nov-Dec	11694737
[Nitroglycerin patch for tocolysis--a prospective randomized comparison with fenoterol by infusion].	2001 Sep-Oct	11727665
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
In vitro sensitization of human bronchus by beta2-adrenergic agonists.	2002 Nov	12376356
The beta2- and beta3-adrenoceptor-mediated relaxation induced by fenoterol in guinea pig taenia caecum.	2002 Oct	12596892
[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
Behaviour of beta 2-adrenoceptors on lymphocytes under continuous and pulsatile tocolysis with Fenoterol.	2003	12661144
Effect of stimulation of beta-adrenergic receptors on neuronal activity in primary motor cortex of the rat.	2003 Apr 10	12668246
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
Reproducibility of forced inspiratory and expiratory volumes after bronchodilation in patients with COPD or asthma.	2003 May	12735677
Supraventricular tachycardia after fenoterol inhalation: report of two cases.	2003 May-Jun	14521024
Science and physicianly practice: are they compatible?	2003 Nov	14678245
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	12967929
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	12975249
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
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
Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol.	2004 Apr 21	15080615
Mechanisms of beta-receptor stimulation-induced improvement of acute lung injury and pulmonary edema.	2004 Aug	15312205
Adrenergic regulation of vascular smooth muscle tone in calf digital artery.	2004 Aug	15305854
Clinical inquiries. Do inhaled beta-agonists control cough in URIs or acute bronchitis?	2004 Aug	15298845
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
Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells.	2004 Feb	14730417
[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
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
Beta 2-agonist treatment enhances uterine oxytocin receptor mRNA expression in pregnant rats.	2004 Sep	15278905
Respimat Soft Mist inhaler versus hydrofluoroalkane metered dose inhaler: patient preference and satisfaction.	2005	15725050
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
Short-acting inhaled beta-2-agonists increased the mortality from chronic obstructive pulmonary disease in observational designs.	2005 Jan	15649676
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
Beta2-agonist administration increases sarcoplasmic reticulum Ca2+-ATPase activity in aged rat skeletal muscle.	2005 Mar	15479951
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.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:51:19 UTC 2021` Edited by `admin` on `Fri Jun 25 21:51:19 UTC 2021`
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

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 [WHO-DD]

Common Name

English

FENOTEROL [INN]

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