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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
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
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Berotec 1mg/mlsolution1 mginhalationBoehringer Ingelheim (Canada) Ltd Ltee1982-12-312008-12-16Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Berotec Aem 100mcg/dosemetered-dose aerosol100 mcginhalation; oralBoehringer Ingelheim (Canada) Ltd Ltee1992-12-312007-11-02Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Berotec Forte Metered Aermetered-dose aerosol0.2 mginhalation; oralBoehringer Ingelheim (Canada) Ltd Ltee1977-12-311997-08-14Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Berotec Tab 2.5mgtablet2.5 mgoralBoehringer Ingelheim (Canada) Ltd Ltee1979-12-312000-07-31Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Berotec Udv Inhalation Solution 0.25mg/mlsolution0.25 mginhalation; oralBoehringer Ingelheim (Canada) Ltd Ltee1994-12-312005-02-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Berotec Udv Inhalation Soluton 0.625mg/mlsolution0.625 mginhalation; oralBoehringer Ingelheim (Canada) Ltd Ltee1994-12-312004-07-16Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
AlveofenPrieto
BerotecBoehringer Ingelheim
Berotec NBoehringer Ingelheim
CenfenolCenter
PartusistenBoehringer Ingelheim
Brand mixtures
NameLabellerIngredients
Duovent UdvBoehringer Ingelheim (Canada) Ltd Ltee
Salts
Name/CASStructureProperties
Fenoterol hydrobromide
ThumbNot applicableDBSALT001185
Categories
UNII22M9P70OQ9
CAS number13392-18-2
WeightAverage: 303.3529
Monoisotopic: 303.147058165
Chemical FormulaC17H21NO4
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Resorcinol
  • Aralkylamine
  • Phenol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Solutioninhalation1 mg
Metered-dose aerosolinhalation; oral100 mcg
Metered-dose aerosolinhalation; oral0.2 mg
Tabletoral2.5 mg
Solutioninhalation; oral0.25 mg
Solutioninhalation; oral0.625 mg
Solutioninhalation; oral
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 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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 ReferencesNot Available
External Links
ATC CodesG02CA03R03AC04R03CC04
AHFS Codes
  • 12:12.08.12
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Fenoterol.
AcetaminophenThe risk or severity of adverse effects can be increased when Fenoterol is combined with Acetaminophen.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Fenoterol is combined with Acetylsalicylic acid.
AminophyllineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Aminophylline.
AmphetamineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Amphetamine.
ArformoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Arformoterol.
ArmodafinilThe risk or severity of adverse effects can be increased when Fenoterol is combined with Armodafinil.
ArticaineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Articaine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Fenoterol.
BenzphetamineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Benzphetamine.
ButalbitalThe risk or severity of adverse effects can be increased when Fenoterol is combined with Butalbital.
CaffeineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Caffeine.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Fenoterol.
Cimetropium BromideFenoterol may increase the anticholinergic activities of Cimetropium Bromide.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Fenoterol.
CocaineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Cocaine.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Fenoterol is combined with Dexmethylphenidate.
DextroamphetamineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Dextroamphetamine.
DiethylpropionThe risk or severity of adverse effects can be increased when Fenoterol is combined with Diethylpropion.
DihydrocodeineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Dihydrocodeine.
DipivefrinThe risk or severity of adverse effects can be increased when Fenoterol is combined with Dipivefrin.
DobutamineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Dobutamine.
DopamineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Dopamine.
DoxapramThe risk or severity of adverse effects can be increased when Fenoterol is combined with Doxapram.
DoxofyllineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Fenoterol.
DyphyllineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Dyphylline.
EluxadolineFenoterol may increase the activities of Eluxadoline.
EphedrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Ephedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Epinephrine.
EsmololEsmolol may decrease the activities of Fenoterol.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Fenoterol is combined with Fluticasone Propionate.
FormoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Formoterol.
IndacaterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Indacaterol.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Fenoterol.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Fenoterol is combined with Ipratropium bromide.
IsomethepteneThe risk or severity of adverse effects can be increased when Fenoterol is combined with Isometheptene.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Fenoterol.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Fenoterol.
LevonordefrinThe risk or severity of adverse effects can be increased when Fenoterol is combined with Levonordefrin.
LinezolidLinezolid may increase the hypertensive activities of Fenoterol.
LisdexamfetamineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Lisdexamfetamine.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Fenoterol.
MepivacaineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Mepivacaine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Fenoterol.
MethamphetamineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Methamphetamine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Fenoterol.
MethylphenidateThe risk or severity of adverse effects can be increased when Fenoterol is combined with Methylphenidate.
MidodrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Midodrine.
ModafinilThe risk or severity of adverse effects can be increased when Fenoterol is combined with Modafinil.
MorphineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Morphine.
NabiloneNabilone may increase the tachycardic activities of Fenoterol.
NadololNadolol may decrease the activities of Fenoterol.
NaphazolineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Naphazoline.
NorepinephrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Norepinephrine.
OlodaterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Olodaterol.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Fenoterol.
OxymetazolineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Oxymetazoline.
PhendimetrazineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Phendimetrazine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Fenoterol.
PheniramineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Pheniramine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Fenoterol.
PhentermineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Phentermine.
PhenylephrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Phenylephrine.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Fenoterol.
PirbuterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Pirbuterol.
ProcyclidineFenoterol may increase the anticholinergic activities of Procyclidine.
PropylhexedrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Propylhexedrine.
PseudoephedrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Pseudoephedrine.
RacepinephrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Racepinephrine.
RamosetronFenoterol may increase the activities of Ramosetron.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Fenoterol.
SalbutamolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Salbutamol.
SalmeterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Salmeterol.
TacrineThe therapeutic efficacy of Fenoterol can be decreased when used in combination with Tacrine.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Fenoterol.
TerbutalineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Terbutaline.
TheophyllineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Theophylline.
TorasemideFenoterol may increase the hypokalemic activities of Torasemide.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Fenoterol.
TrichlormethiazideFenoterol may increase the hypokalemic activities of Trichlormethiazide.
TriprolidineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Triprolidine.
VilanterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Vilanterol.
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