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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 of FENOTEROL

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
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

Sources: books.google.ru/books?id=W53vCAAAQBAJ&pg=PA379

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
193.0 nM [Kd]
Target ID: P08588
Gene ID: 153.0
Gene Symbol: ADRB1
Target Organism: Homo sapiens (Human)
13600.0 nM [Ki]
Target ID: P13945
Gene ID: 155.0
Gene Symbol: ADRB3
Target Organism: Homo sapiens (Human)
55700.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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.
Primary
Unknown

Approved Use

Tocolysis with the aim to reduce premature labor and fetal mortality.
PubMed

PubMed

TitleDatePubMed
[NO synthase activity in epitheliocytes of the rat bronchi following inhalation administration of adrenergic agonists and guanosine triphosphate].
2001
Inhaled short-acting beta2-agonists versus ipratropium for acute exacerbations of chronic obstructive pulmonary disease.
2001
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
Effects of fenoterol on beta-adrenoceptor and muscarinic M2 receptor function in bovine tracheal smooth muscle.
2001 May 11
The predictive value of asthma medications to identify individuals with asthma--a study in German general practices.
2001 Nov
Sonographic cervical volumetry in higher order multiple gestation.
2001 Nov-Dec
[Nitroglycerin patch for tocolysis--a prospective randomized comparison with fenoterol by infusion].
2001 Sep-Oct
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
Airway responsiveness and airway remodeling after chronic exposure to procaterol and fenoterol in guinea pigs in vivo.
2002 Dec
In vitro sensitization of human bronchus by beta2-adrenergic agonists.
2002 Nov
The beta2- and beta3-adrenoceptor-mediated relaxation induced by fenoterol in guinea pig taenia caecum.
2002 Oct
[Continuous fenoterol inhalation by children with severe acute asthma: immediate clinical effects].
2002 Sep-Oct
[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
Behaviour of beta 2-adrenoceptors on lymphocytes under continuous and pulsatile tocolysis with Fenoterol.
2003
Effect of stimulation of beta-adrenergic receptors on neuronal activity in primary motor cortex of the rat.
2003 Apr 10
Maternal and fetal side effects of tocolysis using transdermal nitroglycerin or intravenous fenoterol combined with magnesium sulfate.
2003 Jan 10
[Side effects of fenoterol inhalation in asthmatic children].
2003 Jul-Aug
Reproducibility of forced inspiratory and expiratory volumes after bronchodilation in patients with COPD or asthma.
2003 May
Supraventricular tachycardia after fenoterol inhalation: report of two cases.
2003 May-Jun
Science and physicianly practice: are they compatible?
2003 Nov
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
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
Inhibition by reproterol of cAMP PDE in intact mastocytoma P-815 cells.
2004
[Effect of high doses of broncholytics on the state of cardiovascular system during treatment of sever exacerbation of bronchial asthma].
2004
[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
Effects of dopexamine in comparison with fenoterol on carbohydrate, fat and protein metabolism in healthy volunteers.
2004 Apr
Effect of Bryophyllum pinnatum versus fenoterol on uterine contractility.
2004 Apr 15
Enzyme-linked immunosorbent assay development for the beta-adrenergic agonist zilpaterol.
2004 Apr 21
Mechanisms of beta-receptor stimulation-induced improvement of acute lung injury and pulmonary edema.
2004 Aug
Adrenergic regulation of vascular smooth muscle tone in calf digital artery.
2004 Aug
Clinical inquiries. Do inhaled beta-agonists control cough in URIs or acute bronchitis?
2004 Aug
Suboptimal management of subclinical hypothyroidism.
2004 Aug 16
Beneficial effects of chronic pharmacological manipulation of beta-adrenoreceptor subtype signaling in rodent dilated ischemic cardiomyopathy.
2004 Aug 31
G-protein-coupled receptor chromatographic stationary phases. 2. Ligand-induced conformational mobility in an immobilized beta2-adrenergic receptor.
2004 Dec 15
Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells.
2004 Feb
[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
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
Improved delivery of ipratropium bromide/fenoterol from Respimat Soft Mist Inhaler in patients with COPD.
2004 May
Differential effects of beta2-adrenoceptor desensitization on the IgE-dependent release of chemical mediators from cultured human mast cells.
2004 Oct
Betamimetics for inhibiting preterm labour.
2004 Oct 18
Nociceptin inhibits vanilloid TRPV-1-mediated neurosensitization induced by fenoterol in human isolated bronchi.
2004 Sep
Beta 2-agonist treatment enhances uterine oxytocin receptor mRNA expression in pregnant rats.
2004 Sep
Respimat Soft Mist inhaler versus hydrofluoroalkane metered dose inhaler: patient preference and satisfaction.
2005
N-coumaroyldopamine and N-caffeoyldopamine increase cAMP via beta 2-adrenoceptors in myelocytic U937 cells.
2005 Apr
Past, present and future--beta2-adrenoceptor agonists in asthma management.
2005 Feb
Short-acting inhaled beta-2-agonists increased the mortality from chronic obstructive pulmonary disease in observational designs.
2005 Jan
Exposure to TARC alters beta2-adrenergic receptor signaling in human peripheral blood T lymphocytes.
2005 Jul
Chronic beta-agonist administration affects cardiac function of adult but not old rats, independent of beta-adrenoceptor density.
2005 Jul
Beta2-agonist administration increases sarcoplasmic reticulum Ca2+-ATPase activity in aged rat skeletal muscle.
2005 Mar
Self-limitation of intravenous tocolysis with beta2-adrenergic agonists is mediated through receptor G protein uncoupling.
2005 May
Patents

Sample Use Guides

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
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
  • Download
Name Type Language
FENOTEROL
INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
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
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
WHO-ATC G02CA03
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
NCI_THESAURUS C48149
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
WHO-VATC QG02CA03
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
WHO-VATC QR03AL01
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
WHO-ATC R03CC04
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
WHO-VATC QR03CC04
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
NCI_THESAURUS C319
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
WHO-VATC QR03AC04
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
WHO-ATC R03AC04
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
Code System Code Type Description
CAS
13392-18-2
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
IUPHAR
557
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY
ChEMBL
CHEMBL32800
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY
EPA CompTox
13392-18-2
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY
NCI_THESAURUS
C65659
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY
MESH
D005280
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY
RXCUI
4333
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY RxNorm
EVMPD
SUB07579MIG
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY
MERCK INDEX
M5282
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY Merck Index
INN
3073
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY
WIKIPEDIA
FENOTEROL
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY
DRUG BANK
DB01288
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY
DRUG CENTRAL
1155
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY
FDA UNII
22M9P70OQ9
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY
CAS
130156-24-0
Created by admin on Fri Jun 25 21:51:19 UTC 2021 , Edited by admin on Fri Jun 25 21:51:19 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE ENANTIOMER->RACEMATE
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY