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
Catecholamines suppress leptin release from in vitro differentiated subcutaneous human adipocytes in primary culture via beta1- and beta2-adrenergic receptors.	2000 Sep	11022189
[Significance of bronchospasm in the development of bronchial obstruction in exogenous allergic alveolitis].	2001	11508233
[Effect of ipratropium bromide on histamine-induced bronchoconstriction in subjects with chronic airway obstruction].	2001	11474870
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
Improved delivery of fenoterol plus ipratropium bromide using Respimat compared with a conventional metered dose inhaler.	2001 Feb	11334124
Screening of beta-2 agonists and confirmation of fenoterol, orciprenaline, reproterol and terbutaline with gas chromatography-mass spectrometry as tetrahydroisoquinoline derivatives.	2001 Feb 10	11232861
High-performance liquid chromatographic determination of the beta2-selective adrenergic agonist fenoterol in human plasma after fluorescence derivatization.	2001 Feb 10	11232847
Functional properties of atypical beta-adrenoceptors on the guinea pig duodenum.	2001 Mar 23	11282125
Effects of fenoterol on beta-adrenoceptor and muscarinic M2 receptor function in bovine tracheal smooth muscle.	2001 May 11	11426849
[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
[Pharmacodynamics of inhalation broncholytic agents introduced in a single dose by nebulizer in patients with severe exacerbation of bronchial asthma].	2002	11980113
Beta 2-agonist fenoterol has greater effects on contractile function of rat skeletal muscles than clenbuterol.	2002 Dec	12388476
What is the optimal treatment strategy for chronic obstructive pulmonary disease exacerbations?	2002 May	12030735
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
Behaviour of beta 2-adrenoceptors on lymphocytes under continuous and pulsatile tocolysis with Fenoterol.	2003	12661144
Synthesis and preliminary evaluation of (R,R)(S,S) 5-(2-(2-[4-(2-[(18)F]fluoroethoxy)phenyl]-1-methylethylamino)-1-hydroxyethyl)-benzene-1,3-diol ([(18)F]FEFE) for the in vivo visualisation and quantification of the beta2-adrenergic receptor status in lung.	2003 Aug 18	12873495
Inhaling beta(2)-agonist with heliox-driven in bronchial asthma.	2003 Jul	12890374
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
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
Clinical inquiries. Do inhaled beta-agonists control cough in URIs or acute bronchitis?	2004 Aug	15298845
G-protein-coupled receptor chromatographic stationary phases. 2. Ligand-induced conformational mobility in an immobilized beta2-adrenergic receptor.	2004 Dec 15	15595859
Atypical beta-adrenoceptor subtypes mediate relaxations of rabbit corpus cavernosum.	2004 May	14752060
Betamimetics for inhibiting preterm labour.	2004 Oct 18	15495104
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
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