Identification

Name
Formoterol
Accession Number
DB00983  (APRD00641)
Type
Small Molecule
Groups
Approved, Investigational
Description

Formoterol is a long-acting (12 hours) beta2-agonist used in the management of asthma and/or chronic obstructive pulmonary disease (COPD). Inhaled formoterol works like other beta2-agonists, causing bronchodilatation through relaxation of the smooth muscle in the airway so as to treat the exacerbation of asthma.

Structure
Thumb
Synonyms
  • 2'-Hydroxy-5'-(1-hydroxy-2-((P-methoxy-alpha-methylphenethyl)amino)ethyl)formanilide
  • 2'-Hydroxy-5'-{1-hydroxy-2-[(P-methoxy-alpha-methylphenethyl)amino]ethyl}formanilide
  • Formoterolum
  • N-[2-Hydroxy-5-(1-hydroxy-2-{[2-(4-methoxyphenyl)-1-methylethyl]amino}ethyl)phenyl]formamide
Product Ingredients
IngredientUNIICASInChI Key
Formoterol fumarateW34SHF8J2K183814-30-4RATSWNOMCHFQGJ-AYJOUMQSSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ForadilCapsule12 ug/1Respiratory (inhalation)Physicians Total Care, Inc.2004-05-28Not applicableUs
ForadilCapsule12 ug/1Respiratory (inhalation)Merck Sharp & Dohme Limited2001-02-162017-01-31Us
ForadilCapsule12 ug/1Respiratory (inhalation)Merck Sharp & Dohme Limited2001-02-162017-01-31Us
Foradil Dry Powder Capsules for InhalationCapsule12 mcgRespiratory (inhalation)Novartis1997-07-08Not applicableCanada
Oxeze TurbuhalerPowder6 mcgRespiratory (inhalation)Astra Zeneca1998-03-12Not applicableCanada
Oxeze TurbuhalerPowder12 mcgRespiratory (inhalation)Astra Zeneca1998-03-12Not applicableCanada
PerforomistSolution20 ug/2mLRespiratory (inhalation)Mylan Specialty2007-10-01Not applicableUs
International/Other Brands
Foradile / Oxis Turbuhaler
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bevespi AerosphereFormoterol fumarate (4.8 ug/1) + Glycopyrronium bromide (9 ug/1)Aerosol, meteredRespiratory (inhalation)Astra Zeneca Lp2016-10-03Not applicableUs
DuleraFormoterol fumarate (5 ug/1) + Mometasone furoate (200 ug/1)AerosolRespiratory (inhalation)A S Medication Solutions2010-06-222017-06-20Us
DuleraFormoterol fumarate (5 ug/1) + Mometasone furoate (100 ug/1)AerosolRespiratory (inhalation)Merck Sharp & Dohme Limited2010-06-22Not applicableUs
DuleraFormoterol fumarate (5 ug/1) + Mometasone furoate (200 ug/1)AerosolRespiratory (inhalation)Merck Sharp & Dohme Limited2010-06-22Not applicableUs
SymbicortFormoterol fumarate (4.5 ug/1) + Budesonide (160 ug/1)AerosolRespiratory (inhalation)Astra Zeneca Lp2007-05-29Not applicableUs
SymbicortFormoterol fumarate (4.5 ug/1) + Budesonide (160 ug/1)AerosolRespiratory (inhalation)A S Medication Solutions2007-05-292017-06-20Us
SymbicortFormoterol fumarate (4.5 ug/1) + Budesonide (80 ug/1)AerosolRespiratory (inhalation)Astra Zeneca Lp2007-05-29Not applicableUs
SymbicortFormoterol fumarate (4.5 ug/1) + Budesonide (160 ug/1)AerosolRespiratory (inhalation)Remedy Repack2016-04-042017-02-23Us
Categories
UNII
5ZZ84GCW8B
CAS number
73573-87-2
Weight
Average: 344.4049
Monoisotopic: 344.173607266
Chemical Formula
C19H24N2O4
InChI Key
BPZSYCZIITTYBL-UHFFFAOYSA-N
InChI
InChI=1S/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)
IUPAC Name
N-[2-hydroxy-5-(1-hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)phenyl]formamide
SMILES
COC1=CC=C(CC(C)NCC(O)C2=CC(NC=O)=C(O)C=C2)C=C1

Pharmacology

Indication

For use as long-term maintenance treatment of asthma in patients 6 years of age and older with reversible obstructive airways disease, including patients with symptoms of nocturnal asthma, who are using optimal corticosteroid treatment and experiencing regular or frequent breakthrough symptoms requiring use of a short-acting bronchodilator. Not indicated for asthma that can be successfully managed with occasional use of an inhaled, short-acting beta2-adrenergic agonist. Also used for the prevention of exercise-induced bronchospasm, as well as long-term treatment of bronchospasm associated with COPD.

Structured Indications
Pharmacodynamics

Formoterol is a long-acting selective beta2-adrenergic receptor agonist (beta2-agonist). Inhaled formoterol fumarate acts locally in the lung as a bronchodilator. In vitro studies have shown that formoterol has more than 200-fold greater agonist activity at beta2-receptors than at beta1- receptors. Although beta2-receptors are the predominant adrenergic receptors in bronchial smooth muscle and beta1-receptors are the predominant receptors in the heart, there are also beta2-receptors in the human heart comprising 10%-50% of the total beta-adrenergic receptors. The precise function of these receptors has not been established, but they raise the possibility that even highly selective beta2- agonists may have cardiac effects.

Mechanism of action

The pharmacologic effects of beta2-adrenoceptor agonist drugs, including formoterol, are at least in part attributable to stimulation of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3', 5'-adenosine monophosphate (cyclic AMP). Increased cyclic AMP levels cause relaxation of bronchial smooth muscle and inhibits the release of pro-inflammatory mast-cell mediators such as histamine and leukotrienes. Formoterol also inhibits histamine-induced plasma albumin extravasation in anesthetized guinea pigs and inhibits allergen-induced eosinophil influx in dogs with airway hyper-responsiveness. The relevance of these in vitro and animal findings to humans is unknown.

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

Rapidly absorbed into plasma following administration by oral inhalation. It is likely that the majority of the inhaled formoterol delivered is swallowed and then absorbed from the gastrointestinal tract.

Volume of distribution
Not Available
Protein binding

The binding of formoterol to human plasma proteins in vitro was 61%-64% at concentrations from 0.1 to 100 ng/mL. Binding to human serum albumin in vitro was 31%-38% over a range of 5 to 500 ng/mL. The concentrations of formoterol used to assess the plasma protein binding were higher than those achieved in plasma following inhalation of a single 120 µg dose.

Metabolism

Metabolized primarily by direct glucuronidation at either the phenolic or aliphatic hydroxyl group and O-demethylation followed by glucuronide conjugation at either phenolic hydroxyl groups. Minor pathways involve sulfate conjugation of formoterol and deformylation followed by sulfate conjugation. The most prominent pathway involves direct conjugation at the phenolic hydroxyl group. The second major pathway involves O-demethylation followed by conjugation at the phenolic 2'-hydroxyl group. Four cytochrome P450 isozymes (CYP2D6, CYP2C19, CYP2C9 and CYP2A6) are involved in the O-demethylation of formoterol.

Route of elimination

Following inhalation of a 12 mcg or 24 mcg dose by 16 patients with asthma, about 10% and 15%-18% of the total dose was excreted in the urine as unchanged formoterol and direct conjugates of formoterol, respectively.

Half life

10 hours

Clearance
  • Renal cl=150 mL/min [Healty subjects receiving oral administration of 80 mcg]
Toxicity

An overdosage is likely to lead to effects that are typical of ß2-adrenergic stimulants: nausea, vomiting, headache, tremor, somnolence, palpitations, tachycardia, ventricular arrhythmias, metabolic acidosis, hypokalemia, hyperglycemia.

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

Interactions

Drug Interactions
DrugInteractionDrug group
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 Formoterol.Experimental
AbirateroneThe serum concentration of Formoterol can be increased when it is combined with Abiraterone.Approved
AcebutololAcebutolol may decrease the bronchodilatory activities of Formoterol.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Formoterol.Approved, Investigational
AlprenololAlprenolol may decrease the bronchodilatory activities of Formoterol.Approved, Withdrawn
Ambroxol acefyllinateThe risk or severity of adverse effects can be increased when Ambroxol acefyllinate is combined with Formoterol.Experimental, Investigational
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Formoterol.Illicit, Withdrawn
AminophyllineThe risk or severity of adverse effects can be increased when Aminophylline is combined with Formoterol.Approved
AmiodaroneFormoterol may increase the QTc-prolonging activities of Amiodarone.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Formoterol.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Formoterol.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Formoterol.Approved, Illicit
AnagrelideFormoterol may increase the QTc-prolonging activities of Anagrelide.Approved
AprepitantThe metabolism of Formoterol can be increased when combined with Aprepitant.Approved, Investigational
ArmodafinilThe metabolism of Formoterol can be decreased when combined with Armodafinil.Approved, Investigational
Arsenic trioxideFormoterol may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherFormoterol may increase the QTc-prolonging activities of Artemether.Approved
AsenapineFormoterol may increase the QTc-prolonging activities of Asenapine.Approved
AtenololAtenolol may decrease the bronchodilatory activities of Formoterol.Approved
AtomoxetineAtomoxetine may increase the tachycardic activities of Formoterol.Approved
AtosibanThe risk or severity of adverse effects can be increased when Formoterol is combined with Atosiban.Approved, Investigational
AzithromycinFormoterol may increase the QTc-prolonging activities of Azithromycin.Approved
BedaquilineFormoterol may increase the QTc-prolonging activities of Bedaquiline.Approved
BendroflumethiazideFormoterol may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Formoterol.Withdrawn
Benzylpenicilloyl PolylysineFormoterol may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Formoterol can be decreased when used in combination with Betahistine.Approved
BetaxololThe metabolism of Formoterol can be decreased when combined with Betaxolol.Approved
BisoprololBisoprolol may decrease the bronchodilatory activities of Formoterol.Approved
BopindololBopindolol may decrease the bronchodilatory activities of Formoterol.Approved
BortezomibThe metabolism of Formoterol can be decreased when combined with Bortezomib.Approved, Investigational
BrofaromineThe risk or severity of adverse effects can be increased when Brofaromine is combined with Formoterol.Experimental
BromocriptineBromocriptine may increase the hypertensive activities of Formoterol.Approved, Investigational
BucindololBucindolol may decrease the vasoconstricting activities of Formoterol.Investigational
BumetanideFormoterol may increase the hypokalemic activities of Bumetanide.Approved
BunazosinBunazosin may decrease the vasoconstricting activities of Formoterol.Investigational
BupranololBupranolol may decrease the bronchodilatory activities of Formoterol.Approved
BupropionThe metabolism of Formoterol can be decreased when combined with Bupropion.Approved
CabergolineCabergoline may increase the hypertensive activities of Formoterol.Approved
CaffeineThe risk or severity of adverse effects can be increased when Caffeine is combined with Formoterol.Approved
CapecitabineThe metabolism of Formoterol can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Formoterol can be increased when combined with Carbamazepine.Approved, Investigational
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Formoterol.Withdrawn
CarteololCarteolol may decrease the bronchodilatory activities of Formoterol.Approved
CarvedilolCarvedilol may decrease the vasoconstricting activities of Formoterol.Approved, Investigational
CelecoxibThe metabolism of Formoterol can be decreased when combined with Celecoxib.Approved, Investigational
CeliprololCeliprolol may decrease the bronchodilatory activities of Formoterol.Approved, Investigational
CeritinibThe serum concentration of Formoterol can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Formoterol can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChloroquineFormoterol may increase the QTc-prolonging activities of Chloroquine.Approved, Vet Approved
ChlorothiazideFormoterol may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorpromazineFormoterol may increase the QTc-prolonging activities of Chlorpromazine.Approved, Vet Approved
ChlorthalidoneFormoterol may increase the hypokalemic activities of Chlorthalidone.Approved
CholecalciferolThe metabolism of Formoterol can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Formoterol can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Formoterol can be decreased when combined with Cinacalcet.Approved
CiprofloxacinFormoterol may increase the QTc-prolonging activities of Ciprofloxacin.Approved, Investigational
CisaprideFormoterol may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CitalopramFormoterol may increase the QTc-prolonging activities of Citalopram.Approved
ClarithromycinFormoterol may increase the QTc-prolonging activities of Clarithromycin.Approved
ClemastineThe metabolism of Formoterol can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Formoterol can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Formoterol can be decreased when combined with Clomipramine.Approved, Vet Approved
CloranololCloranolol may decrease the bronchodilatory activities of Formoterol.Experimental
ClotrimazoleThe metabolism of Formoterol can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineFormoterol may increase the QTc-prolonging activities of Clozapine.Approved
CobicistatThe serum concentration of Formoterol can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Formoterol can be decreased when combined with Cocaine.Approved, Illicit
CrisaboroleThe metabolism of Formoterol can be decreased when combined with Crisaborole.Approved
CrizotinibFormoterol may increase the QTc-prolonging activities of Crizotinib.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Formoterol.Approved
CyclopenthiazideFormoterol may increase the hypokalemic activities of Cyclopenthiazide.Experimental
CyclosporineThe metabolism of Formoterol can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Formoterol can be decreased when it is combined with Dabrafenib.Approved
DarifenacinThe metabolism of Formoterol can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Formoterol can be increased when it is combined with Darunavir.Approved
DelavirdineThe metabolism of Formoterol can be decreased when combined with Delavirdine.Approved
DesfluraneDesflurane may increase the arrhythmogenic activities of Formoterol.Approved
DesipramineThe metabolism of Formoterol can be decreased when combined with Desipramine.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Formoterol.Approved
DibenzepinThe risk or severity of adverse effects can be increased when Dibenzepin is combined with Formoterol.Experimental
Diethyl etherDiethyl ether may increase the arrhythmogenic activities of Formoterol.Experimental
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Formoterol.Approved
DiphenhydramineThe metabolism of Formoterol can be decreased when combined with Diphenhydramine.Approved
DisopyramideFormoterol may increase the QTc-prolonging activities of Disopyramide.Approved
DofetilideFormoterol may increase the QTc-prolonging activities of Dofetilide.Approved
DolasetronFormoterol may increase the QTc-prolonging activities of Dolasetron.Approved
DomperidoneFormoterol may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DosulepinThe metabolism of Formoterol can be decreased when combined with Dosulepin.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Formoterol.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Formoterol.Approved
DronedaroneFormoterol may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolFormoterol may increase the QTc-prolonging activities of Droperidol.Approved, Vet Approved
DuloxetineDuloxetine may increase the tachycardic activities of Formoterol.Approved
DyphyllineThe risk or severity of adverse effects can be increased when Dyphylline is combined with Formoterol.Approved
EfavirenzThe metabolism of Formoterol can be decreased when combined with Efavirenz.Approved, Investigational
EliglustatFormoterol may increase the QTc-prolonging activities of Eliglustat.Approved
EnfluraneEnflurane may increase the arrhythmogenic activities of Formoterol.Approved, Investigational, Vet Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Formoterol.Approved
ErgonovineErgonovine may increase the hypertensive activities of Formoterol.Approved
ErgotamineErgotamine may increase the hypertensive activities of Formoterol.Approved
ErythromycinFormoterol may increase the QTc-prolonging activities of Erythromycin.Approved, Vet Approved
EscitalopramFormoterol may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
Eslicarbazepine acetateThe metabolism of Formoterol can be decreased when combined with Eslicarbazepine acetate.Approved
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Formoterol.Investigational
EsmololEsmolol may decrease the bronchodilatory activities of Formoterol.Approved
EsomeprazoleThe metabolism of Formoterol can be decreased when combined with Esomeprazole.Approved, Investigational
Etacrynic acidFormoterol may increase the hypokalemic activities of Etacrynic acid.Approved
EtravirineThe metabolism of Formoterol can be decreased when combined with Etravirine.Approved
FlecainideFormoterol may increase the QTc-prolonging activities of Flecainide.Approved, Withdrawn
FloxuridineThe metabolism of Formoterol can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Formoterol can be decreased when combined with Fluconazole.Approved
FluorouracilThe metabolism of Formoterol can be decreased when combined with Fluorouracil.Approved
FluoxetineFormoterol may increase the QTc-prolonging activities of Fluoxetine.Approved, Vet Approved
FlupentixolFormoterol may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
FluvastatinThe metabolism of Formoterol can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Formoterol can be decreased when combined with Fluvoxamine.Approved, Investigational
FosphenytoinThe metabolism of Formoterol can be increased when combined with Fosphenytoin.Approved
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Formoterol.Approved, Investigational, Vet Approved
FurosemideFormoterol may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
Gadobenic acidFormoterol may increase the QTc-prolonging activities of Gadobenic acid.Approved
GemfibrozilThe metabolism of Formoterol can be decreased when combined with Gemfibrozil.Approved
GemifloxacinFormoterol may increase the QTc-prolonging activities of Gemifloxacin.Approved, Investigational
GoserelinFormoterol may increase the QTc-prolonging activities of Goserelin.Approved
GranisetronFormoterol may increase the QTc-prolonging activities of Granisetron.Approved, Investigational
HaloperidolFormoterol may increase the QTc-prolonging activities of Haloperidol.Approved
HalothaneHalothane may increase the arrhythmogenic activities of Formoterol.Approved, Vet Approved
HarmalineThe risk or severity of adverse effects can be increased when Harmaline is combined with Formoterol.Experimental
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Formoterol.Experimental
HydrochlorothiazideFormoterol may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideFormoterol may increase the hypokalemic activities of Hydroflumethiazide.Approved, Investigational
IbutilideFormoterol may increase the QTc-prolonging activities of Ibutilide.Approved
IloperidoneFormoterol may increase the QTc-prolonging activities of Iloperidone.Approved
ImipramineThe metabolism of Formoterol can be decreased when combined with Imipramine.Approved
IndapamideFormoterol may increase the hypokalemic activities of Indapamide.Approved
IndinavirThe metabolism of Formoterol can be decreased when combined with Indinavir.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Formoterol.Withdrawn
IprindoleThe risk or severity of adverse effects can be increased when Iprindole is combined with Formoterol.Experimental
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Formoterol.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Formoterol.Withdrawn
IrbesartanThe metabolism of Formoterol can be decreased when combined with Irbesartan.Approved, Investigational
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Formoterol.Approved
IsofluraneIsoflurane may increase the arrhythmogenic activities of Formoterol.Approved, Vet Approved
IsoniazidThe metabolism of Formoterol can be decreased when combined with Isoniazid.Approved
KetoconazoleThe metabolism of Formoterol can be decreased when combined with Ketoconazole.Approved, Investigational
LabetalolLabetalol may decrease the vasoconstricting activities of Formoterol.Approved
LeflunomideThe metabolism of Formoterol can be decreased when combined with Leflunomide.Approved, Investigational
LenvatinibFormoterol may increase the QTc-prolonging activities of Lenvatinib.Approved
LeuprolideFormoterol may increase the QTc-prolonging activities of Leuprolide.Approved, Investigational
LevofloxacinFormoterol may increase the QTc-prolonging activities of Levofloxacin.Approved, Investigational
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Formoterol.Approved
LobeglitazoneThe metabolism of Formoterol can be decreased when combined with Lobeglitazone.Approved, Investigational
LofepramineThe risk or severity of adverse effects can be increased when Lofepramine is combined with Formoterol.Experimental
LopinavirFormoterol may increase the QTc-prolonging activities of Lopinavir.Approved
LorcaserinThe metabolism of Formoterol can be decreased when combined with Lorcaserin.Approved
LosartanThe metabolism of Formoterol can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Formoterol can be decreased when combined with Lovastatin.Approved, Investigational
LoxapineThe risk or severity of adverse effects can be increased when Formoterol is combined with Loxapine.Approved
LuliconazoleThe serum concentration of Formoterol can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Formoterol can be decreased when it is combined with Lumacaftor.Approved
LumefantrineFormoterol may increase the QTc-prolonging activities of Lumefantrine.Approved
ManidipineThe metabolism of Formoterol can be decreased when combined with Manidipine.Approved, Investigational
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Formoterol.Withdrawn
MepindololMepindolol may decrease the bronchodilatory activities of Formoterol.Experimental
MethadoneFormoterol may increase the QTc-prolonging activities of Methadone.Approved
MethotrimeprazineThe metabolism of Formoterol can be decreased when combined with Methotrimeprazine.Approved
MethoxyfluraneMethoxyflurane may increase the arrhythmogenic activities of Formoterol.Approved, Investigational, Vet Approved
MethyclothiazideFormoterol may increase the hypokalemic activities of Methyclothiazide.Approved
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Formoterol.Approved, Investigational
MethylergometrineMethylergometrine may increase the hypertensive activities of Formoterol.Approved
MetolazoneFormoterol may increase the hypokalemic activities of Metolazone.Approved
MetoprololThe metabolism of Formoterol can be decreased when combined with Metoprolol.Approved, Investigational
MidostaurinThe metabolism of Formoterol can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Formoterol can be increased when it is combined with Mifepristone.Approved, Investigational
MilnacipranMilnacipran may increase the tachycardic activities of Formoterol.Approved
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Formoterol.Approved
MirabegronThe metabolism of Formoterol can be decreased when combined with Mirabegron.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Formoterol.Approved
MoclobemideThe metabolism of Formoterol can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Formoterol can be decreased when combined with Modafinil.Approved, Investigational
MoxifloxacinFormoterol may increase the QTc-prolonging activities of Moxifloxacin.Approved, Investigational
NebivololNebivolol may decrease the bronchodilatory activities of Formoterol.Approved, Investigational
NelfinavirThe metabolism of Formoterol can be decreased when combined with Nelfinavir.Approved
NevirapineThe metabolism of Formoterol can be decreased when combined with Nevirapine.Approved
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Formoterol.Withdrawn
NicardipineThe metabolism of Formoterol can be decreased when combined with Nicardipine.Approved
NicotineThe metabolism of Formoterol can be decreased when combined with Nicotine.Approved
NilotinibFormoterol may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
Nitrous oxideNitrous oxide may increase the arrhythmogenic activities of Formoterol.Approved, Vet Approved
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Formoterol.Approved
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Formoterol.Withdrawn
OfloxacinFormoterol may increase the QTc-prolonging activities of Ofloxacin.Approved
OmeprazoleThe metabolism of Formoterol can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OndansetronFormoterol may increase the QTc-prolonging activities of Ondansetron.Approved
OpipramolThe risk or severity of adverse effects can be increased when Opipramol is combined with Formoterol.Investigational
OxprenololOxprenolol may decrease the bronchodilatory activities of Formoterol.Approved
PaliperidoneFormoterol may increase the QTc-prolonging activities of Paliperidone.Approved
PanobinostatThe serum concentration of Formoterol can be increased when it is combined with Panobinostat.Approved, Investigational
PantoprazoleThe metabolism of Formoterol can be decreased when combined with Pantoprazole.Approved
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Formoterol.Approved
ParoxetineThe metabolism of Formoterol can be decreased when combined with Paroxetine.Approved, Investigational
PazopanibFormoterol may increase the QTc-prolonging activities of Pazopanib.Approved
Peginterferon alfa-2bThe serum concentration of Formoterol can be decreased when it is combined with Peginterferon alfa-2b.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Formoterol.Approved, Investigational
PentamidineFormoterol may increase the QTc-prolonging activities of Pentamidine.Approved
PentobarbitalThe metabolism of Formoterol can be increased when combined with Pentobarbital.Approved, Vet Approved
PerflutrenFormoterol may increase the QTc-prolonging activities of Perflutren.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Formoterol.Approved
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Formoterol.Withdrawn
PhenobarbitalThe metabolism of Formoterol can be increased when combined with Phenobarbital.Approved
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Formoterol.Withdrawn
PhenytoinThe metabolism of Formoterol can be increased when combined with Phenytoin.Approved, Vet Approved
PimozideFormoterol may increase the QTc-prolonging activities of Pimozide.Approved
PiretanideFormoterol may increase the hypokalemic activities of Piretanide.Experimental
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Formoterol.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Formoterol.Withdrawn
PolythiazideFormoterol may increase the hypokalemic activities of Polythiazide.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Formoterol.Approved
PrimaquineFormoterol may increase the QTc-prolonging activities of Primaquine.Approved
PrimidoneThe metabolism of Formoterol can be increased when combined with Primidone.Approved, Vet Approved
ProcainamideFormoterol may increase the QTc-prolonging activities of Procainamide.Approved
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Formoterol.Approved
PromazineFormoterol may increase the QTc-prolonging activities of Promazine.Approved, Vet Approved
PropafenoneFormoterol may increase the QTc-prolonging activities of Propafenone.Approved
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Formoterol.Approved
PyrimethamineThe metabolism of Formoterol can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuetiapineFormoterol may increase the QTc-prolonging activities of Quetiapine.Approved
QuinethazoneFormoterol may increase the hypokalemic activities of Quinethazone.Approved
QuinidineFormoterol may increase the QTc-prolonging activities of Quinidine.Approved
QuinineFormoterol may increase the QTc-prolonging activities of Quinine.Approved
RanolazineThe metabolism of Formoterol can be decreased when combined with Ranolazine.Approved, Investigational
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Formoterol.Approved
RifampicinThe metabolism of Formoterol can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Formoterol can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Formoterol can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Formoterol can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Formoterol can be decreased when combined with Ropinirole.Approved, Investigational
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Formoterol.Withdrawn
SaquinavirFormoterol may increase the QTc-prolonging activities of Saquinavir.Approved, Investigational
SecobarbitalThe metabolism of Formoterol can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Formoterol.Approved, Investigational, Vet Approved
SertralineThe metabolism of Formoterol can be decreased when combined with Sertraline.Approved
SevofluraneSevoflurane may increase the arrhythmogenic activities of Formoterol.Approved, Vet Approved
SildenafilThe metabolism of Formoterol can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinSilodosin may decrease the vasoconstricting activities of Formoterol.Approved
SorafenibThe metabolism of Formoterol can be decreased when combined with Sorafenib.Approved, Investigational
SotalolFormoterol may increase the QTc-prolonging activities of Sotalol.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Formoterol.Approved
StiripentolThe metabolism of Formoterol can be decreased when combined with Stiripentol.Approved
SulfadiazineThe metabolism of Formoterol can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Formoterol can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Formoterol can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TamsulosinTamsulosin may decrease the vasoconstricting activities of Formoterol.Approved, Investigational
TelavancinFormoterol may increase the QTc-prolonging activities of Telavancin.Approved
TelithromycinFormoterol may increase the QTc-prolonging activities of Telithromycin.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Formoterol.Approved
TerbinafineThe metabolism of Formoterol can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TertatololTertatolol may decrease the bronchodilatory activities of Formoterol.Experimental
TetrabenazineFormoterol may increase the QTc-prolonging activities of Tetrabenazine.Approved
TheophyllineThe risk or severity of adverse effects can be increased when Theophylline is combined with Formoterol.Approved
ThioridazineFormoterol may increase the QTc-prolonging activities of Thioridazine.Approved, Withdrawn
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Formoterol.Approved, Investigational
TicagrelorThe metabolism of Formoterol can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Formoterol can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Formoterol can be decreased when combined with Tipranavir.Approved, Investigational
TolbutamideThe metabolism of Formoterol can be decreased when combined with Tolbutamide.Approved
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Formoterol.Approved
TopiramateThe metabolism of Formoterol can be decreased when combined with Topiramate.Approved
TopiroxostatThe metabolism of Formoterol can be decreased when combined with Topiroxostat.Approved, Investigational
TorasemideFormoterol may increase the hypokalemic activities of Torasemide.Approved
ToremifeneFormoterol may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Formoterol.Experimental
TranylcypromineThe metabolism of Formoterol can be decreased when combined with Tranylcypromine.Approved
TrichlormethiazideFormoterol may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrichloroethyleneTrichloroethylene may increase the arrhythmogenic activities of Formoterol.Experimental
TrimazosinTrimazosin may decrease the vasoconstricting activities of Formoterol.Experimental
TrimethoprimThe metabolism of Formoterol can be decreased when combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Formoterol.Approved
UrapidilUrapidil may decrease the vasoconstricting activities of Formoterol.Investigational
Valproic AcidThe metabolism of Formoterol can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Formoterol can be decreased when combined with Valsartan.Approved, Investigational
VandetanibFormoterol may increase the QTc-prolonging activities of Vandetanib.Approved
VemurafenibFormoterol may increase the QTc-prolonging activities of Vemurafenib.Approved
VenlafaxineVenlafaxine may increase the tachycardic activities of Formoterol.Approved
VoriconazoleThe metabolism of Formoterol can be decreased when combined with Voriconazole.Approved, Investigational
XenonXenon may increase the arrhythmogenic activities of Formoterol.Experimental
ZafirlukastThe metabolism of Formoterol can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneFormoterol may increase the QTc-prolonging activities of Ziprasidone.Approved
ZucapsaicinThe metabolism of Formoterol can be decreased when combined with Zucapsaicin.Approved
ZuclopenthixolFormoterol may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Jan W. Trofast, Edib Jakupovic, Katarina L. Mansson, "Process for preparing formoterol and related compounds." U.S. Patent US5434304, issued August, 1992.

US5434304
General References
  1. Bartow RA, Brogden RN: Formoterol. An update of its pharmacological properties and therapeutic efficacy in the management of asthma. Drugs. 1998 Feb;55(2):303-22. [PubMed:9506248]
  2. Cheer SM, Scott LJ: Formoterol: a review of its use in chronic obstructive pulmonary disease. Am J Respir Med. 2002;1(4):285-300. [PubMed:14720051]
  3. Steiropoulos P, Tzouvelekis A, Bouros D: Formoterol in the management of chronic obstructive pulmonary disease. Int J Chron Obstruct Pulmon Dis. 2008;3(2):205-15. [PubMed:18686730]
  4. Faulds D, Hollingshead LM, Goa KL: Formoterol. A review of its pharmacological properties and therapeutic potential in reversible obstructive airways disease. Drugs. 1991 Jul;42(1):115-37. [PubMed:1718682]
  5. Op't Holt TB: Inhaled beta agonists. Respir Care. 2007 Jul;52(7):820-32. [PubMed:17594727]
External Links
Human Metabolome Database
HMDB15118
KEGG Compound
C07805
PubChem Compound
3410
PubChem Substance
46507099
ChemSpider
3292
BindingDB
86453
ChEBI
63082
ChEMBL
CHEMBL1256786
Therapeutic Targets Database
DAP000247
PharmGKB
PA134687907
IUPHAR
3465
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Formoterol
ATC Codes
R03AL05 — Formoterol and aclidinium bromideR03AK07 — Formoterol and budesonideR03AK11 — Formoterol and fluticasoneR03AK08 — Formoterol and beclometasoneR03AK09 — Formoterol and mometasoneR03AC13 — Formoterol
AHFS Codes
  • 12:12.08.12 — Selective Beta 2-adrenergic Agonists
FDA label
Download (1.48 MB)
MSDS
Download (36.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
1CompletedTreatmentAsthma Bronchial5
1CompletedTreatmentAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)1
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)2
1CompletedTreatmentHealthy Volunteers2
1, 2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2CompletedPreventionAcute Respiratory Distress Syndrome (ARDS)1
2CompletedTreatmentAirway Obstruction / Asthma Bronchial1
2CompletedTreatmentAllogeneic Stem Cell Transplantation / Obliterative Bronchiolitis1
2CompletedTreatmentAsthma Bronchial10
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)20
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Chronic Obstructive Pulmonary Disease - COPD1
2CompletedTreatmentExercised Induced Asthma1
2CompletedTreatmentIdiopathic Pulmonary Fibrosis (IPF)1
2CompletedTreatmentMild Persistent Asthma1
2CompletedTreatmentObstructive Airway Disease1
2CompletedTreatmentPulmonary Disease, Chronic Obstructive2
2CompletedTreatmentStable Asthma1
2RecruitingTreatmentAsthma Bronchial1
2RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2TerminatedPreventionCryptogenic Organizing Pneumonia / Lung Diseases, Interstitial / Obliterative Bronchiolitis / Respiratory Tract Infections (RTI)1
2Unknown StatusTreatmentAsthma Bronchial1
2WithdrawnTreatmentAsthma Bronchial1
2WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2, 3CompletedTreatmentAllergies1
2, 3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Lung Diseases, Obstructive / Pulmonary Disease, Chronic Obstructive1
3Active Not RecruitingTreatmentAsthma Bronchial1
3Active Not RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3CompletedNot AvailableAsthma Bronchial1
3CompletedTreatmentAsthma Bronchial38
3CompletedTreatmentBronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Emphysema1
3CompletedTreatmentCOPD Patients1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)21
3CompletedTreatmentMild or Moderate Asthma1
3CompletedTreatmentPulmonary Disease, Chronic Obstructive6
3RecruitingTreatmentAsthma Bronchial2
3RecruitingTreatmentAsthma Bronchial / Bioequivalence1
3RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)2
3RecruitingTreatmentSmoking1
3Unknown StatusTreatmentEmphysema / Poor Sleeping Quality1
3Unknown StatusTreatmentPulmonary Disease, Chronic Obstructive1
3WithdrawnPreventionExercise-Induced Bronchoconstriction (EIB)1
4CompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)2
4CompletedTreatmentAcute Bronchial Obstruction, Asthma1
4CompletedTreatmentAsthma Bronchial9
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)11
4CompletedTreatmentPersistent Asthma1
4CompletedTreatmentPulmonary Disease, Chronic Obstructive3
4Not Yet RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingNot AvailableAsthma Bronchial1
4RecruitingBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentBronchial Asthma1
4RecruitingTreatmentBronchiectasis / Chronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentPulmonary Disease,Chronic Obstructive1
4RecruitingTreatmentSevere IgE-mediated Asthma1
4TerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD)2
4TerminatedTreatmentExercised Induced Asthma1
4TerminatedTreatmentSafety of Long Acting Beta Agnoists1
4Unknown StatusDiagnosticChronic Obstructive Pulmonary Disease (COPD) / Emphysema / Small Airway Disease1
4Unknown StatusTreatmentAsthma Bronchial1
4Unknown StatusTreatmentBronchial Asthma1
4WithdrawnTreatmentAsthma Bronchial1
4WithdrawnTreatmentChronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Emphysema1
4WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)2
Not AvailableCompletedNot AvailableAsthma Bronchial4
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailablePerception of Physicians & Patients of AMD1
Not AvailableCompletedNot AvailablePulmonary Disease, Chronic Obstructive1
Not AvailableCompletedDiagnosticAsthma Bronchial1
Not AvailableCompletedSupportive CareChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedTreatmentAsthma Bronchial1
Not AvailableCompletedTreatmentDiabetes, Diabetes Mellitus Type 11
Not AvailableNot Yet RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableRecruitingNot AvailableAsthma Bronchial1
Not AvailableRecruitingNot AvailablePulmonary Disease, Chronic Obstructive1
Not AvailableRecruitingPreventionAcute Exacerbation of Chronic Obstructive Pulmonary Disease / Air Pollution1
Not AvailableTerminatedTreatmentAsthma Bronchial1
Not AvailableUnknown StatusNot AvailableAllergic Rhinitis (AR) / Asthma Bronchial1
Not AvailableUnknown StatusTreatmentAcute Exacerbation of Chronic Obstructive Pulmonary Disease1
Not AvailableUnknown StatusTreatmentAsthma Bronchial1

Pharmacoeconomics

Manufacturers
  • Novartis pharmaceuticals corp
  • Dey pharma lp
Packagers
Dosage forms
FormRouteStrength
Aerosol, meteredRespiratory (inhalation)
AerosolRespiratory (inhalation)
CapsuleRespiratory (inhalation)12 ug/1
CapsuleRespiratory (inhalation)12 mcg
PowderRespiratory (inhalation)12 mcg
PowderRespiratory (inhalation)6 mcg
SolutionRespiratory (inhalation)20 ug/2mL
Prices
Unit descriptionCostUnit
Formoterol fumarate powder1346.4USD g
Foradil Aerolizer 60 12 mcg capsule Box170.72USD box
Foradil aerolizer 12 mcg cap2.83USD each
Foradil 12 mcg Capsule0.88USD capsule
Oxeze Turbuhaler 12 mcg/dose Metered Inhalation Powder0.82USD dose
Oxeze Turbuhaler 6 mcg/dose Metered Inhalation Powder0.61USD dose
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6182655No1996-12-052016-12-05Us
US6887459No2000-11-282020-11-28Us
US6488027No1999-03-082019-03-08Us
US6814953No2001-06-222021-06-22Us
US7348362No2001-06-222021-06-22Us
US7462645No2001-06-222021-06-22Us
US6667344No2001-06-222021-06-22Us
US7759328Yes2003-07-292023-07-29Us
US7897646Yes1999-03-092019-03-09Us
US8143239Yes2003-07-292023-07-29Us
US8461211Yes1999-03-092019-03-09Us
US8575137Yes2003-07-292023-07-29Us
US6123924No1997-09-262017-09-26Us
US7967011Yes2002-02-112022-02-11Us
US8616196Yes2009-10-072029-10-07Us
US8387615Yes2005-05-102025-05-10Us
US7587988Yes2006-10-102026-10-10Us
US7367333Yes1999-05-112019-05-11Us
US8528545Yes2009-04-162029-04-16Us
US8875699Yes2005-05-102025-05-10Us
US8623922No2001-06-222021-06-22Us
US6068832No1997-08-272017-08-27Us
US7067502No2000-05-212020-05-21Us
US7566705No2000-05-212020-05-21Us
US9463161No2010-05-282030-05-28Us
US9415009No2010-05-282030-05-28Us
US8808713No2010-05-282030-05-28Us
US8324266No2010-05-282030-05-28Us
US8703806No2010-05-282030-05-28Us
US8815258No2011-03-172031-03-17Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySlightly (as fumarate salt)Not Available
logP2.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0416 mg/mLALOGPS
logP1.91ALOGPS
logP1.06ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.61ChemAxon
pKa (Strongest Basic)9.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.82 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity97.87 m3·mol-1ChemAxon
Polarizability36.56 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8991
Blood Brain Barrier-0.8026
Caco-2 permeable-0.6916
P-glycoprotein substrateSubstrate0.747
P-glycoprotein inhibitor INon-inhibitor0.8773
P-glycoprotein inhibitor IINon-inhibitor0.8561
Renal organic cation transporterNon-inhibitor0.8818
CYP450 2C9 substrateNon-substrate0.714
CYP450 2D6 substrateNon-substrate0.7086
CYP450 3A4 substrateSubstrate0.5556
CYP450 1A2 substrateNon-inhibitor0.6609
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8757
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8442
Ames testNon AMES toxic0.7517
CarcinogenicityNon-carcinogens0.8704
BiodegradationNot ready biodegradable0.992
Rat acute toxicity2.4047 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9611
hERG inhibition (predictor II)Non-inhibitor0.6602
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

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 / Phenoxy compounds / Methoxybenzenes / Anisoles / Aralkylamines / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / 1,2-aminoalcohols / Propargyl-type 1,3-dipolar organic compounds
show 5 more
Substituents
Amphetamine or derivatives / Phenylpropane / Phenoxy compound / Anisole / Phenol ether / Methoxybenzene / Alkyl aryl ether / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenylethanolamines, secondary alcohol, phenols, formamides, secondary amino compound (CHEBI:63082)

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. Handley DA, Senanayake CH, Dutczak W, Benovic JL, Walle T, Penn RB, Wilkinson HS, Tanoury GJ, Andersson RG, Johansson F, Morley J: Biological actions of formoterol isomers. Pulm Pharmacol Ther. 2002;15(2):135-45. [PubMed:12090787]
  2. Scola AM, Chong LK, Suvarna SK, Chess-Williams R, Peachell PT: Desensitisation of mast cell beta2-adrenoceptor-mediated responses by salmeterol and formoterol. Br J Pharmacol. 2004 Jan;141(1):163-71. Epub 2003 Dec 8. [PubMed:14662724]
  3. Ryall JG, Sillence MN, Lynch GS: Systemic administration of beta2-adrenoceptor agonists, formoterol and salmeterol, elicit skeletal muscle hypertrophy in rats at micromolar doses. Br J Pharmacol. 2006 Mar;147(6):587-95. [PubMed:16432501]
  4. Lofdahl CG, Svedmyr N: Formoterol fumarate, a new beta 2-adrenoceptor agonist. Acute studies of selectivity and duration of effect after inhaled and oral administration. Allergy. 1989 May;44(4):264-71. [PubMed:2544117]
  5. Kompa AR, Molenaar P, Summers RJ: Beta-adrenoceptor regulation and functional responses in the guinea-pig following chronic administration of the long-acting beta 2-adrenoceptor agonist formoterol. Naunyn Schmiedebergs Arch Pharmacol. 1995 Jun;351(6):576-88. [PubMed:7675115]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. Bartow RA, Brogden RN: Formoterol. An update of its pharmacological properties and therapeutic efficacy in the management of asthma. Drugs. 1998 Feb;55(2):303-22. [PubMed:9506248]
  8. Cheer SM, Scott LJ: Formoterol: a review of its use in chronic obstructive pulmonary disease. Am J Respir Med. 2002;1(4):285-300. [PubMed:14720051]
  9. Steiropoulos P, Tzouvelekis A, Bouros D: Formoterol in the management of chronic obstructive pulmonary disease. Int J Chron Obstruct Pulmon Dis. 2008;3(2):205-15. [PubMed:18686730]
  10. Faulds D, Hollingshead LM, Goa KL: Formoterol. A review of its pharmacological properties and therapeutic potential in reversible obstructive airways disease. Drugs. 1991 Jul;42(1):115-37. [PubMed:1718682]
  11. Op't Holt TB: Inhaled beta agonists. Respir Care. 2007 Jul;52(7):820-32. [PubMed:17594727]
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]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [PubMed:17627976]
  2. Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [PubMed:10671910]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [PubMed:17627976]
  2. Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [PubMed:10671910]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [PubMed:17627976]
  2. Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [PubMed:10671910]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, Manchee GR: A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos. 2007 Oct;35(10):1797-805. Epub 2007 Jul 12. [PubMed:17627976]
  2. Zhang M, Fawcett JP, Kennedy JM, Shaw JP: Stereoselective glucuronidation of formoterol by human liver microsomes. Br J Clin Pharmacol. 2000 Feb;49(2):152-7. [PubMed:10671910]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33