Fenoterol

Identification

Summary

Fenoterol is a beta-2 adrenergic agonist and bronchodilator used for the symptomatic treatment of asthma.

Generic Name
Fenoterol
DrugBank Accession Number
DB01288
Background

Fenoterol is an adrenergic beta-2 agonist that is used as a bronchodilator and tocolytic.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 303.3529
Monoisotopic: 303.147058165
Chemical Formula
C17H21NO4
Synonyms
  • 1-(3,5-dihydroxyphenyl)-1-hydroxy-2-((4-hydroxyphenyl)isopropylamino)ethane
  • 1-(p-hydroxyphenyl)-2-((β-hydroxy-β-(3',5'-dihydroxyphenyl))ethyl)aminopropane
  • 3,5-dihydroxy-α-(((p-hydroxy-α-methylphenethyl)amino)methyl)benzyl alcohol
  • 5-{1-Hydroxy-2-[2-(4-hydroxy-phenyl)-1-methyl-ethylamino]-ethyl}-benzene-1,3-diol
  • Fenoterol
  • Fenoterolum
  • Phenoterol
External IDs
  • TH-1165

Pharmacology

Indication

Fenoterol is used for the treatment of asthma.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Prophylaxis ofAsthma, exercise-induced••••••••••••
Symptomatic treatment ofAsthmatic attack••••••••••••
Adjunct therapy in treatment ofBronchial asthma••••••••••••
Used in combination to manageSevere copd exacerbationCombination Product in combination with: Ipratropium (DB00332)••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Fenoterol is a beta agonist designed to open up the airways to the lungs by decreasing bronchconstriction.

Mechanism of action

Beta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.

TargetActionsOrganism
ABeta-2 adrenergic receptor
agonist
Humans
UBeta-1 adrenergic receptor
agonist
Humans
UBeta-3 adrenergic receptor
agonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic.

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of overdose include angina (chest pain), dizziness, dry mouth, fatigue, flu-like symptoms, headache, heart irregularities, high or low blood pressure, high blood sugar, insomnia, muscle cramps, nausea, nervousness, rapid heartbeat, seizures, and tremor.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe therapeutic efficacy of Fenoterol can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Fenoterol is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Fenoterol is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Fenoterol.
AclidiniumThe risk or severity of adverse effects can be increased when Fenoterol is combined with Aclidinium.
Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Fenoterol hydrobromideRLI45Z99RB1944-12-3SGZRQMALQBXAIQ-NRNQBQMASA-N
International/Other Brands
Alveofen (Prieto) / Berotec (Boehringer Ingelheim) / Berotec N (Boehringer Ingelheim) / Cenfenol (Center) / Partusisten (Boehringer Ingelheim)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Berotec 1mg/mlSolution1 mg / mLRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1982-12-312008-12-16Canada flag
Berotec Aem 100mcg/doseAerosol, metered100 mcg / actRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1992-12-312007-11-02Canada flag
Berotec Forte Metered AerAerosol, metered0.2 mg / nsRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1977-12-311997-08-14Canada flag
Berotec Tab 2.5mgTablet2.5 mgOralBoehringer Ingelheim (Canada) Ltd Ltee1979-12-312000-07-31Canada flag
Berotec Udv Inhalation Solution 0.25mg/mlSolution0.25 mg / mLRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1994-12-312005-02-10Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Berodual - DosieraerosolFenoterol hydrobromide (0.05 mg) + Ipratropium bromide monohydrate (0.02 mg)Aerosol, meteredRespiratory (inhalation)Boehringer Ingelheim Rcv Gmb H & Co Kg1981-09-15Not applicableAustria flag
BERODUAL N METERED DOSE INHALERFenoterol hydrobromide (50 mcg) + Ipratropium bromide monohydrate (20 mcg)Aerosol, meteredRespiratory (inhalation)BOEHRINGER INGELHEIM (MALAYSIA) SDN. BHD.2020-09-08Not applicableMalaysia flag
BERODUAL N METERED DOSE INHALERFenoterol hydrobromide (50 mcg/dose) + Ipratropium bromide anhydrous (20 mcg/dose)Aerosol, sprayRespiratory (inhalation)BOEHRINGER INGELHEIM SINGAPORE PTE. LTD.2001-11-30Not applicableSingapore flag
BERODUAL SOLUTIONFenoterol hydrobromide (0.5 mg/ml) + Ipratropium bromide monohydrate (0.25 mg/ml)SolutionRespiratory (inhalation)BOEHRINGER INGELHEIM SINGAPORE PTE. LTD.1989-04-28Not applicableSingapore flag
BERODUAL® HFAFenoterol hydrobromide (0.05 mg) + Ipratropium (0.02 mg)SolutionRespiratory (inhalation)BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG.2006-11-10Not applicableColombia flag

Categories

ATC Codes
R03CC04 — FenoterolR03AL01 — Fenoterol and ipratropium bromideG02CA03 — FenoterolR03AC04 — Fenoterol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Phenylpropanes / Resorcinols / Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
show 1 more
Substituents
1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Amphetamine or derivatives / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary alcohol, secondary amino compound, resorcinols (CHEBI:149226)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
22M9P70OQ9
CAS number
13392-18-2
InChI Key
LSLYOANBFKQKPT-UHFFFAOYSA-N
InChI
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
IUPAC Name
5-(1-hydroxy-2-{[1-(4-hydroxyphenyl)propan-2-yl]amino}ethyl)benzene-1,3-diol
SMILES
CC(CC1=CC=C(O)C=C1)NCC(O)C1=CC(O)=CC(O)=C1

References

Synthesis Reference

Zeile, K., Thoma, O. and Mentrup, A,; U.S. Patent 3,341,593; September 12, 1967; assigned to Boehringer lngelheim GmbH, Germany.

General References
  1. AIFA Product Information: Dosberotec (fenoterol hydrobromide) for inhalation [Link]
Human Metabolome Database
HMDB0015405
KEGG Drug
D04157
PubChem Compound
3343
PubChem Substance
46509099
ChemSpider
3226
BindingDB
50131281
RxNav
4333
ChEBI
149226
ChEMBL
CHEMBL32800
Therapeutic Targets Database
DAP000946
PharmGKB
PA10079
Guide to Pharmacology
GtP Drug Page
Wikipedia
Fenoterol

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
4CompletedTreatmentAcute Bronchial Obstruction, Asthma1somestatusstop reasonjust information to hide
4Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1somestatusstop reasonjust information to hide
3CompletedTreatmentAsthma3somestatusstop reasonjust information to hide
3CompletedTreatmentAsthma / Chronic Obstructive Pulmonary Disease (COPD)1somestatusstop reasonjust information to hide
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)2somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
AerosolBuccal
AerosolRespiratory (inhalation)
SolutionRespiratory (inhalation)
Aerosol, sprayRespiratory (inhalation)50 mcg/dose
SolutionRespiratory (inhalation)0.5 mg/ml
AerosolRespiratory (inhalation)
Aerosol, meteredRespiratory (inhalation)100 µg
SolutionRespiratory (inhalation)1 mg / mL
Aerosol, meteredRespiratory (inhalation)100 mcg / act
Aerosol, meteredRespiratory (inhalation)0.2 mg / ns
GasRespiratory (inhalation)100 UG
TabletOral2.5 mg
SolutionRespiratory (inhalation)0.25 mg / mL
SolutionRespiratory (inhalation)0.625 mg / mL
AerosolRespiratory (inhalation)15 ML
Aerosol, meteredRespiratory (inhalation)100 MCG
Aerosol, meteredRespiratory (inhalation)200 MCG
Powder, meteredRespiratory (inhalation)0.2 MG
SolutionOral1 MG/ML
SolutionRespiratory (inhalation)200 MCG
SprayRespiratory (inhalation)0.5 MG/2ML
SprayRespiratory (inhalation)1.25 MG/2ML
SprayRespiratory (inhalation)5 MG/ML
Syrup0.5 MG/ML
Aerosol, meteredRespiratory (inhalation)
SolutionNasal1.25 mg/4ml
AerosolRespiratory (inhalation)100000 Mcg
SyrupOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)222-223Zeile, K., Thoma, O. and Mentrup, A,; U.S. Patent 3,341,593; September 12, 1967; assigned to Boehringer lngelheim GmbH, Germany.
Predicted Properties
PropertyValueSource
Water Solubility0.162 mg/mLALOGPS
logP1.36ALOGPS
logP1.47Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.85Chemaxon
pKa (Strongest Basic)9.63Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area92.95 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity85 m3·mol-1Chemaxon
Polarizability31.75 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.987
Blood Brain Barrier-0.9294
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.7292
P-glycoprotein inhibitor INon-inhibitor0.9064
P-glycoprotein inhibitor IINon-inhibitor0.946
Renal organic cation transporterNon-inhibitor0.7992
CYP450 2C9 substrateNon-substrate0.7004
CYP450 2D6 substrateNon-substrate0.7055
CYP450 3A4 substrateNon-substrate0.625
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8681
Ames testNon AMES toxic0.8609
CarcinogenicityNon-carcinogens0.9011
BiodegradationNot ready biodegradable0.9174
Rat acute toxicity2.1550 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.813
hERG inhibition (predictor II)Non-inhibitor0.7963
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000i-2900000000-41b22ffada47796cccca
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-7c86ed90b231db502424
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-cbe10ada4ea45a1c990b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-d901c2f8d4959edd3fb8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-5c754c51c284fa4a611f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-3900000000-8521f3088ff1f180cc5b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udr-0927000000-3bbfb7c5db84766576df
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0906000000-834141424313103bb39e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-2930000000-10623fe53f788342c6da
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-4962000000-a66a74324066e07a73ce
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-1910000000-5aea992cbefad6dada12
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-2910000000-b25d04f58d52ad324251
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-175.5997035
predicted
DarkChem Lite v0.1.0
[M-H]-171.78706
predicted
DeepCCS 1.0 (2019)
[M+H]+176.5030035
predicted
DarkChem Lite v0.1.0
[M+H]+174.14507
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.1321035
predicted
DarkChem Lite v0.1.0
[M+Na]+180.2382
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. de Vries B, Roffel AF, Zaagsma J, Meurs H: Effect of fenoterol-induced constitutive beta(2)-adrenoceptor activity on contractile receptor function in airway smooth muscle. Eur J Pharmacol. 2001 Nov 23;431(3):353-9. [Article]
  2. Boterman M, Smits SR, Meurs H, Zaagsma J: Protein kinase C potentiates homologous desensitization of the beta2-adrenoceptor in bovine tracheal smooth muscle. Eur J Pharmacol. 2006 Jan 4;529(1-3):151-6. Epub 2005 Dec 1. [Article]
  3. Marone G, Ambrosio G, Bonaduce D, Genovese A, Triggiani M, Condorelli M: Inhibition of IgE-mediated histamine release from human basophils and mast cells by fenoterol. Int Arch Allergy Appl Immunol. 1984;74(4):356-61. [Article]
  4. Coqueret O, Demarquay D, Lagente V: Role of cyclic AMP in the modulation of IgE production by the beta 2-adrenoceptor agonist, fenoterol. Eur Respir J. 1996 Feb;9(2):220-5. [Article]
  5. Bouillon T, Meineke I, Port R, Hildebrandt R, Gunther K, Gundert-Remy U: Concentration-effect relationship of the positive chronotropic and hypokalaemic effects of fenoterol in healthy women of childbearing age. Eur J Clin Pharmacol. 1996;51(2):153-60. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name
ADRB3
Uniprot ID
P13945
Uniprot Name
Beta-3 adrenergic receptor
Molecular Weight
43518.615 Da
References
  1. Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. [Article]

Drug created at June 28, 2007 15:56 / Updated at June 02, 2024 21:53