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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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Benztropine Mesylateinjection1 mg/mLintramuscular; intravenousAkorn, Inc.2012-08-08Not AvailableUs
Benztropine Mesylateinjection, solution1 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2011-05-31Not AvailableUs
Benztropine Mesylateinjection1 mg/mLintramuscular; intravenousTYA Pharmaceuticals2012-08-08Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Benztropine Mesylateinjection1 mg/mLintramuscular; intravenousWest ward Pharmaceutical Corp2009-09-01Not AvailableUs
Benztropine Mesylateinjection, solution1 mg/mLintramuscular; intravenousAmerican Regent, Inc.2011-02-04Not AvailableUs
Benztropine Mesylatetablet.5 mgoralQualitest Pharmaceuticals2007-08-27Not AvailableUs
Benztropine Mesylatetablet1 mgoralQualitest Pharmaceuticals2007-08-27Not AvailableUs
Benztropine Mesylatetablet2 mgoralQualitest Pharmaceuticals2007-08-27Not AvailableUs
Benztropine Mesylatetablet.5 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-02-28Not AvailableUs
Benztropine Mesylatetablet1 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-02-28Not AvailableUs
Benztropine Mesylatetablet2 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-02-28Not AvailableUs
Benztropine Mesylatetablet.5 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs1996-12-12Not AvailableUs
Benztropine Mesylatetablet1 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs1996-12-12Not AvailableUs
Benztropine Mesylatetablet2 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs1996-12-12Not AvailableUs
Benztropine Mesylatetablet.5 mgoralUpsher Smith Laboratories, Inc.1996-12-12Not AvailableUs
Benztropine Mesylatetablet1 mgoralUpsher Smith Laboratories, Inc.1996-12-12Not AvailableUs
Benztropine Mesylatetablet2 mgoralUpsher Smith Laboratories, Inc.1996-12-12Not AvailableUs
Benztropine Mesylatetablet.5 mgoralMajor Pharmaceuticals2006-02-23Not AvailableUs
Benztropine Mesylatetablet1 mgoralMajor Pharmaceuticals2006-02-16Not AvailableUs
Benztropine Mesylatetablet2 mgoralMajor Pharmaceuticals2006-02-16Not AvailableUs
Benztropine Mesylatetablet2 mgoralRebel Distributors Corp2002-08-13Not AvailableUs
Benztropine Mesylatetablet.5 mgoralREMEDYREPACK INC.2011-09-06Not AvailableUs
Benztropine Mesylatetablet2 mgoralREMEDYREPACK INC.2010-12-09Not AvailableUs
Benztropine Mesylatetablet.5 mgoralCamber Pharmaceutical, Inc.2013-08-01Not AvailableUs
Benztropine Mesylatetablet1 mgoralCamber Pharmaceutical, Inc.2013-08-01Not AvailableUs
Benztropine Mesylatetablet2 mgoralCamber Pharmaceutical, Inc.2013-08-01Not AvailableUs
Benztropine Mesylatetablet1 mgoralPd Rx Pharmaceuticals, Inc.2010-02-28Not AvailableUs
Benztropine Mesylatetablet1 mgoralAphena Pharma Solutions Tennessee, Llc2007-08-27Not AvailableUs
Benztropine Mesylatetablet.5 mgoralAphena Pharma Solutions Tennessee, Llc2007-08-27Not AvailableUs
Benztropine Mesylatetablet.5 mgoralREMEDYREPACK INC.2010-12-09Not AvailableUs
Benztropine Mesylatetablet2 mgoralREMEDYREPACK INC.2011-03-14Not AvailableUs
Benztropine Mesylatetablet1 mgoralREMEDYREPACK INC.2010-12-16Not AvailableUs
Benztropine Mesylatetablet.5 mgoralREMEDYREPACK INC.2011-09-20Not AvailableUs
Benztropine Mesylatetablet1 mgoralREMEDYREPACK INC.2011-05-18Not AvailableUs
Benztropine Mesylatetablet.5 mgoralREMEDYREPACK INC.2011-05-10Not AvailableUs
Benztropine Mesylatetablet1 mgoralREMEDYREPACK INC.2011-05-16Not AvailableUs
Benztropine Mesylatetablet2 mgoralREMEDYREPACK INC.2011-03-10Not AvailableUs
Benztropine Mesylatetablet2 mgoralREMEDYREPACK INC.2011-04-06Not AvailableUs
Benztropine Mesylatetablet1 mgoralREMEDYREPACK INC.2012-11-13Not AvailableUs
Benztropine Mesylatetablet.5 mgoralPliva Inc.1990-09-30Not AvailableUs
Benztropine Mesylatetablet1 mgoralPliva Inc.1990-09-30Not AvailableUs
Benztropine Mesylatetablet2 mgoralPliva Inc.1990-09-30Not AvailableUs
Benztropine Mesylatetablet1 mgoralREMEDYREPACK INC.2013-03-14Not AvailableUs
Benztropine Mesylatetablet2 mgoralREMEDYREPACK INC.2013-03-18Not AvailableUs
Benztropine Mesylatetablet1 mgoralREMEDYREPACK INC.2013-05-08Not AvailableUs
Benztropine Mesylatetablet2 mgoralREMEDYREPACK INC.2013-05-15Not AvailableUs
Benztropine Mesylatetablet1 mgoralREMEDYREPACK INC.2014-03-11Not AvailableUs
Benztropine Mesylatetablet1 mgoralREMEDYREPACK INC.2014-03-11Not AvailableUs
Benztropine Mesylatetablet1 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Benztropine Mesylatetablet1 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Benztropine Mesylatetablet2 mgoralState of Florida DOH Central Pharmacy2013-01-01Not AvailableUs
Benztropine Mesylatetablet.5 mgoralState of Florida DOH Central Pharmacy2013-01-01Not AvailableUs
Benztropine Mesylatetablet2 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Benztropine Mesylatetablet.5 mgoralState of Florida DOH Central Pharmacy2014-11-01Not AvailableUs
Benztropine Mesylatetablet2 mgoralState of Florida DOH Central Pharmacy2014-11-01Not AvailableUs
Benztropine Mesylatetablet1 mgoralState of Florida DOH Central Pharmacy2014-11-01Not AvailableUs
Benztropine Mesylatetablet1 mgoralCardinal Health2002-08-13Not AvailableUs
Benztropine Mesylatetablet.5 mgoralCardinal Health2002-08-13Not AvailableUs
Benztropine Mesylatetablet1 mgoralCardinal Health2010-01-14Not AvailableUs
Benztropine Mesylatetablet1 mgoralCardinal Health2009-10-16Not AvailableUs
Benztropine Mesylatetablet.5 mgoralClinical Solutions Wholesale2007-08-27Not AvailableUs
Benztropine Mesylatetablet1 mgoralClinical Solutions Wholesale2007-08-27Not AvailableUs
Benztropine Mesylatetablet2 mgoralClinical Solutions Wholesale2007-08-27Not AvailableUs
Benztropine Mesylatetablet1 mgoralREMEDYREPACK INC.2014-08-13Not AvailableUs
Benztropine Mesylatetablet.5 mgoralREMEDYREPACK INC.2014-08-25Not AvailableUs
Benztropine Mesylatetablet.5 mgoralREMEDYREPACK INC.2014-12-10Not AvailableUs
Benztropine Mesylatetablet2 mgoralREMEDYREPACK INC.2014-08-28Not AvailableUs
Benztropine Mesylatetablet1 mgoralREMEDYREPACK INC.2014-09-30Not AvailableUs
Benztropine Mesylatetablet2 mgoralDIRECT RX2014-01-01Not AvailableUs
Benztropine Mesylatetablet1 mgoralbryant ranch prepack2007-08-27Not AvailableUs
Benztropine Mesylatetablet2 mgoralbryant ranch prepack2007-08-27Not AvailableUs
Benztropine Mesylatetablet.5 mgoralExcellium Pharmaceutical, Inc,2012-12-01Not AvailableUs
Benztropine Mesylatetablet1 mgoralExcellium Pharmaceutical, Inc,2012-12-01Not AvailableUs
Benztropine Mesylatetablet2 mgoralExcellium Pharmaceutical, Inc,2012-12-01Not AvailableUs
Benztropine Mesylatetablet.5 mgoralCorepharma LLC.2002-08-13Not AvailableUs
Benztropine Mesylatetablet1 mgoralCorepharma LLC.2002-08-13Not AvailableUs
Benztropine Mesylatetablet2 mgoralCorepharma LLC.2002-08-13Not AvailableUs
Benztropine Mesylatetablet1 mgoralTYA Pharmaceuticals2007-08-27Not AvailableUs
Benztropine Mesylatetablet2 mgoralTYA Pharmaceuticals2007-08-27Not AvailableUs
Benztropine Mesylatetablet.5 mgoralRising Pharmaceuticals Inc2002-08-13Not AvailableUs
Benztropine Mesylatetablet1 mgoralRising Pharmaceuticals Inc2002-08-13Not AvailableUs
Benztropine Mesylatetablet2 mgoralRising Pharmaceuticals Inc2002-08-13Not AvailableUs
Benztropine Mesylatetablet1 mgoralDispensing Solutions, Inc.2007-08-27Not AvailableUs
Benztropine Mesylatetablet1 mgoralContract Pharmacy Services Pa2010-06-28Not AvailableUs
Benztropine Mesylatetablet2 mgoralContract Pharmacy Services Pa2010-06-28Not AvailableUs
Benztropine Mesylatetablet.5 mgoralAmerican Health Packaging2010-01-14Not AvailableUs
Benztropine Mesylatetablet1 mgoralAmerican Health Packaging2010-01-14Not AvailableUs
Benztropine Mesylatetablet2 mgoralAmerican Health Packaging2010-01-14Not AvailableUs
Benztropine Mesylatetablet1 mgoralMc Kesson Contract Packaging2011-12-08Not AvailableUs
Benztropine Mesylatetablet.5 mgoralMc Kesson Contract Packaging2013-02-21Not AvailableUs
Benztropine Mesylatetablet1 mgoralMc Kesson Contract Packaging2012-02-07Not AvailableUs
Benztropine Mesylatetablet.5 mgoralBayshore Pharmaceuticals, LLC2014-01-31Not AvailableUs
Benztropine Mesylatetablet1 mgoralBayshore Pharmaceuticals, LLC2014-01-31Not AvailableUs
Benztropine Mesylatetablet2 mgoralBayshore Pharmaceuticals, LLC2014-01-31Not AvailableUs
Over the Counter ProductsNot Available
International Brands
NameCompany
AlveofenPrieto
BerotecBoehringer Ingelheim
Berotec NBoehringer Ingelheim
CenfenolCenter
PartusistenBoehringer Ingelheim
Brand mixtures
Brand NameIngredients
Duovent UDVFenoterol Hydrobromide + Ipratropium Bromide
SaltsNot Available
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
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 substrateNon-inhibitor0.9071
CYP450 2D6 substrateInhibitor0.8932
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Injectionintramuscular; intravenous1 mg/mL
Injection, solutionintramuscular; intravenous1 mg/mL
Tabletoral.5 mg
Tabletoral1 mg
Tabletoral2 mg
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 ReferenceNot Available
External Links
ATC CodesG02CA03R03AC04R03CC04
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

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