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Identification
NameFenoterol
Accession NumberDB01288
Typesmall molecule
Groupsapproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
1-(3,5-Dihydroxyphenyl)-1-hydroxy-2-((4-hydroxyphenyl)isopropylamino)ethaneNot AvailableNot Available
1-(P-Hydroxyphenyl)-2-((beta-hydroxy-beta-(3',5'-dihydroxyphenyl))ethyl)aminopropaneNot AvailableNot Available
3,5-Dihydroxy-alpha-(((P-hydroxy-alpha-methylphenethyl)amino)methyl)benzyl alcoholNot AvailableNot Available
5-{1-hydroxy-2-[2-(4-hydroxy-phenyl)-1-methyl-ethylamino]-ethyl}-benzene-1,3-diolNot AvailableNot Available
FenoterolumLatinINN
PhenoterolNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
AlveofenPrieto
Benztropine MesylateBoehringer Ingelheim
BerotecBoehringer Ingelheim
Berotec NBoehringer Ingelheim
CenfenolCenter
PartusistenBoehringer Ingelheim
Brand mixtures
Brand NameIngredients
Duovent UDVFenoterol Hydrobromide + Ipratropium Bromide
Categories
CAS number13392-18-2
WeightAverage: 303.3529
Monoisotopic: 303.147058165
Chemical FormulaC17H21NO4
InChI KeyLSLYOANBFKQKPT-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenethylamines
Direct parentAmphetamines and Derivatives
Alternative parentsResorcinols; Secondary Alcohols; Polyols; 1,2-Aminoalcohols; Enols; Dialkylamines; Polyamines
Substituentsresorcinol; phenol derivative; 1,2-aminoalcohol; secondary alcohol; polyol; polyamine; secondary amine; secondary aliphatic amine; enol; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Pharmacology
IndicationFenoterol is used for the treatment of asthma.
PharmacodynamicsFenoterol is a beta agonist designed to open up the airways to the lungs by decreasing bronchconstriction.
Mechanism of actionBeta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.987
Blood Brain Barrier - 0.9294
Caco-2 permeable - 0.8957
P-glycoprotein substrate Substrate 0.7292
P-glycoprotein inhibitor I Non-inhibitor 0.9064
P-glycoprotein inhibitor II Non-inhibitor 0.946
Renal organic cation transporter Non-inhibitor 0.7992
CYP450 2C9 substrate Non-substrate 0.7004
CYP450 2D6 substrate Non-substrate 0.7055
CYP450 3A4 substrate Non-substrate 0.625
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.8308
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8681
Ames test Non AMES toxic 0.8609
Carcinogenicity Non-carcinogens 0.9011
Biodegradation Not ready biodegradable 0.9174
Rat acute toxicity 2.1550 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.813
hERG inhibition (predictor II) Non-inhibitor 0.7963
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Aerosol, meteredRespiratory (inhalation)
Aerosol, meteredRespiratory (inhalation)
SolutionRespiratory (inhalation)
SolutionRespiratory (inhalation)
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point222-223Zeile, 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 solubility1.62e-01 g/lALOGPS
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 area92.95ChemAxon
rotatable bond count6ChemAxon
refractivity85ChemAxon
polarizability31.75ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
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 ReferenceNot Available
External Links
ResourceLink
PubChem Compound3343
PubChem Substance46509099
ChemSpider3226
BindingDB50131281
ChEBI149226
ChEMBLCHEMBL32800
Therapeutic Targets DatabaseDAP000946
PharmGKBPA10079
IUPHAR557
Guide to Pharmacology557
Drug Product Database541389
WikipediaFenoterol
ATC CodesR03CC04G02CA03R03AC04
AHFS Codes
  • 12:12.08.12
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololAntagonism
AlseroxylonIncreased arterial pressure
AmitriptylineThe tricyclic antidepressant, amitriptyline, may increase the sympathomimetic effect of fenoterol.
AmoxapineThe tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of fenoterol.
AtenololAntagonism
BetaxololBeta-Blockers (Beta-1 Selective) like betaxolol may diminish the bronchodilatory effect of Beta2-Agonists like fenoterol. Therapy should be monitored.
BevantololAntagonism
BisoprololAntagonism
CarteololAntagonism
CarvedilolAntagonism
ClomipramineThe tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of fenoterol.
DeserpidineIncreased arterial pressure
DesipramineThe tricyclic antidepressant, desipramine, increases the sympathomimetic effect of fenoterol.
DoxepinThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of fenoterol.
EsmololAntagonism
ImipramineThe tricyclic antidepressant, imipramine, increases the sympathomimetic effect of fenoterol.
IsocarboxazidIncreased arterial pressure
LabetalolAntagonism
LinezolidPossible increase of arterial pressure
MethyldopaIncreased arterial pressure
MetoprololAntagonism
MidodrineIncreased arterial pressure
MoclobemideMoclobemide increases the sympathomimetic effect of fenoterol.
NadololAntagonism
NortriptylineThe tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of fenoterol.
OxprenololAntagonism
PargylineIncreased arterial pressure
PenbutololAntagonism
PhenelzineIncreased arterial pressure
PindololAntagonism
PractololAntagonism
PropranololAntagonism
ProtriptylineThe tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of fenoterol.
RasagilineIncreased arterial pressure
ReserpineIncreased arterial pressure
SotalolAntagonism
TimololAntagonism
TranylcypromineIncreased arterial pressure
TrimipramineThe tricyclic antidepressant, trimipramine, increases the sympathomimetic effect of fenoterol.
Food Interactions
  • Take without regard to meals.

Targets

1. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

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
  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
  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
  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
  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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Beta-1 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

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

3. Beta-3 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Beta-3 adrenergic receptor P13945 Details

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

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Drug created on June 28, 2007 09:56 / Updated on April 22, 2014 13:56