Identification

Name
Fenoterol
Accession Number
DB01288
Type
Small Molecule
Groups
Approved, Investigational
Description

An adrenergic beta-2 agonist that is used as a bronchodilator and tocolytic. [PubChem]

Structure
Thumb
Synonyms
  • 1-(3,5-Dihydroxyphenyl)-1-hydroxy-2-((4-hydroxyphenyl)isopropylamino)ethane
  • 1-(P-Hydroxyphenyl)-2-((beta-hydroxy-beta-(3',5'-dihydroxyphenyl))ethyl)aminopropane
  • 3,5-Dihydroxy-alpha-(((P-hydroxy-alpha-methylphenethyl)amino)methyl)benzyl alcohol
  • 5-{1-hydroxy-2-[2-(4-hydroxy-phenyl)-1-methyl-ethylamino]-ethyl}-benzene-1,3-diol
  • Fenoterolum
  • Phenoterol
Product Ingredients
IngredientUNIICASInChI Key
Fenoterol hydrobromideRLI45Z99RB1944-12-3SGZRQMALQBXAIQ-NRNQBQMASA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Berotec 1mg/mlSolution1 mgRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1982-12-312008-12-16Canada
Berotec Aem 100mcg/doseAerosol, metered100 mcgOral; Respiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1992-12-312007-11-02Canada
Berotec Forte Metered AerAerosol, metered0.2 mgOral; Respiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1977-12-311997-08-14Canada
Berotec Tab 2.5mgTablet2.5 mgOralBoehringer Ingelheim (Canada) Ltd Ltee1979-12-312000-07-31Canada
Berotec Udv Inhalation Solution 0.25mg/mlSolution0.25 mgOral; Respiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1994-12-312005-02-10Canada
Berotec Udv Inhalation Soluton 0.625mg/mlSolution0.625 mgOral; Respiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1994-12-312004-07-16Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Duovent UdvFenoterol hydrobromide (0.3125 mg) + Ipratropium bromide (0.125 mg)SolutionOral; Respiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1995-12-312017-01-31Canada
International/Other Brands
Alveofen (Prieto) / Berotec (Boehringer Ingelheim) / Berotec N (Boehringer Ingelheim) / Cenfenol (Center) / Partusisten (Boehringer Ingelheim)
Categories
UNII
22M9P70OQ9
CAS number
13392-18-2
Weight
Average: 303.3529
Monoisotopic: 303.147058165
Chemical Formula
C17H21NO4
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

Pharmacology

Indication

Fenoterol is used for the treatment of asthma.

Associated Conditions
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
Human
UBeta-1 adrenergic receptor
agonist
Human
UBeta-3 adrenergic receptor
agonist
Human
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
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.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Fenoterol.
AcebutololThe therapeutic efficacy of Fenoterol can be decreased when used in combination with Acebutolol.
AcepromazineAcepromazine may decrease the vasoconstricting activities of Fenoterol.
AlclometasoneThe risk or severity of hypokalemia can be increased when Alclometasone is combined with Fenoterol.
AlfuzosinThe therapeutic efficacy of Fenoterol can be decreased when used in combination with Alfuzosin.
AlprenololAlprenolol may decrease the bronchodilatory activities of Fenoterol.
AmcinonideThe risk or severity of hypokalemia can be increased when Amcinonide is combined with Fenoterol.
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Fenoterol.
AmitriptylineThe therapeutic efficacy of Fenoterol can be decreased when used in combination with Amitriptyline.
AmitriptylinoxideThe risk or severity of adverse effects can be increased when Amitriptylinoxide is combined with Fenoterol.
Food Interactions
  • Take without regard to meals.

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
Not Available
External Links
Human Metabolome Database
HMDB0015405
PubChem Compound
3343
PubChem Substance
46509099
ChemSpider
3226
BindingDB
50131281
ChEBI
149226
ChEMBL
CHEMBL32800
Therapeutic Targets Database
DAP000946
PharmGKB
PA10079
IUPHAR
557
Guide to Pharmacology
GtP Drug Page
Wikipedia
Fenoterol
ATC Codes
R03AL01 — Fenoterol and ipratropium bromideR03AC04 — FenoterolR03CC04 — FenoterolG02CA03 — Fenoterol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAsthma Bronchial1
3CompletedTreatmentPulmonary Disease, Chronic Obstructive1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SolutionRespiratory (inhalation)1 mg
Aerosol, meteredOral; Respiratory (inhalation)100 mcg
Aerosol, meteredOral; Respiratory (inhalation)0.2 mg
TabletOral2.5 mg
SolutionOral; Respiratory (inhalation)0.25 mg
SolutionOral; Respiratory (inhalation)0.625 mg
SolutionOral; Respiratory (inhalation)
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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

Taxonomy

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
Amphetamine or derivatives / Phenylpropane / Resorcinol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine / 1,2-aminoalcohol / Secondary alcohol / Secondary aliphatic amine
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary alcohol, secondary amino compound, resorcinols (CHEBI:149226)

Targets

Kind
Protein
Organism
Human
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. [PubMed:11730729]
  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. [PubMed:16324695]
  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. [PubMed:6203844]
  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. [PubMed:8777955]
  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. [PubMed:8911881]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
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. [PubMed:14730417]
Kind
Protein
Organism
Human
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. [PubMed:14730417]

Drug created on June 28, 2007 09:56 / Updated on August 02, 2018 07:50