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Identification
NameArformoterol
Accession NumberDB01274
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionArformoterol is a bronchodilator. It works by relaxing muscles in the airways to improve breathing. Arformoterol inhalation is used to prevent bronchoconstriction in people with chronic obstructive pulmonary disease, including chronic bronchitis and emphysema. The use of arformoterol is pending revision due to safety concerns in regards to an increased risk of severe exacerbation of asthma symptoms, leading to hospitalization as well as death in some patients using long acting beta agonists for the treatment of asthma.
Structure
Thumb
Synonyms
(-)-Formoterol
(R,R)-formoterol
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Brovanasolution15 ug/2mLrespiratory (inhalation)Sunovion Pharmaceuticals Inc.2007-04-01Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Arformoterol tartrate
ThumbNot applicableDBSALT001387
Categories
UNIIF91H02EBWT
CAS number67346-49-0
WeightAverage: 344.4049
Monoisotopic: 344.173607266
Chemical FormulaC19H24N2O4
InChI KeyInChIKey=BPZSYCZIITTYBL-YJYMSZOUSA-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)/t13-,19+/m1/s1
IUPAC Name
N-{2-hydroxy-5-[(1R)-1-hydroxy-2-{[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]phenyl}formamide
SMILES
COC1=CC=C(C[C@@H](C)NC[[email protected]](O)C2=CC(NC=O)=C(O)C=C2)C=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
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Aralkylamine
  • Phenol
  • Alkyl aryl ether
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
  • N-[2-hydroxy-5-(1-hydroxy-2-\{[1-(4-methoxyphenyl)propan-2-yl]amino\}ethyl)phenyl]formamide (CHEBI:408174 )
Pharmacology
IndicationA bronchodilator used for the long term, symptomatic treatment of reversible bronchoconstriction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema.
PharmacodynamicsArformoterol, the active (R,R)-enantiomer of formoterol, is a selective long-acting β2-adrenergic receptor agonist (beta2-agonist) that has two-fold greater potency than racemic formoterol (which contains both the (S,S) and (R,R)-enantiomers). The (S,S)-enantiomer is about 1,000-fold less potent as a β2-agonist than the (R,R)-enantiomer. Arformoterol seems to have little or no effect on β1-adrenergic receptors.
Mechanism of actionWhile it is recognized that β2-receptors are the predominant adrenergic receptors in bronchial smooth muscle and β1-receptors are the predominant receptors in the heart, data indicate that there are also β2-receptors in the human heart comprising 10% to 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 β2-agonists may have cardiac effects. The pharmacologic effects of β2-adrenoceptor agonist drugs, including arformoterol, 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 intracellular cyclic AMP levels cause relaxation of bronchial smooth muscle and inhibition of release of proinflammatory mediators from cells, especially from mast cells. In vitro tests show that arformoterol is an inhibitor of the release of mast cell mediators, such as histamine and leukotrienes, from the human lung. Arformoterol also inhibits histamine-induced plasma albumin extravasation in anesthetized guinea pigs and inhibits allergen-induced eosinophil influx in dogs with airway hyper-response.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingThe binding of arformoterol to human plasma proteins in vitro was 52-65% at concentrations of 0.25, 0.5 and 1.0 ng/mL of radiolabeled arformoterol.
Metabolism

Arformoterol was almost entirely metabolized following oral administration of 35 mcg of radiolabeled arformoterol in eight healthy subjects. Direct conjugation of arformoterol with glucuronic acid was the major metabolic pathway. O-Desmethylation is a secondary route catalyzed by the CYP enzymes CYP2D6 and CYP2C19.

Route of eliminationAfter administration of a single oral dose of radiolabeled arformoterol to eight healthy male subjects, 63% of the total radioactive dose was recovered in urine and 11% in feces within 48 hours. Direct glucuronidation of arformoterol is mediated by several UGT enzymes and is the primary elimination route.
Half lifeIn COPD patients given 15 mcg inhaled arformoterol twice a day for 14 days, the mean terminal half-life of arformoterol was 26 hours.
Clearance
  • renal cl=8.9 L/hr [Healthy male subjects]
ToxicityA death was reported in dogs after a single oral dose of 5 mg/kg (approximately 4500 times the maximum recommended daily inhalation dose in adults on a mg/m2 basis). As with all inhaled sympathomimetic medications, cardiac arrest and even death may be associated with an overdose.
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+0.8991
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Solutionrespiratory (inhalation)15 ug/2mL
Prices
Unit descriptionCostUnit
Brovana 15 mcg/2 ml solution3.41USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5795564 No1995-04-032012-04-03Us
US6040344 No1996-11-122016-11-12Us
US6472563 No2001-11-092021-11-09Us
US6667344 No2001-06-222021-06-22Us
US6720453 No2001-11-092021-11-09Us
US6814953 No2001-06-222021-06-22Us
US7145036 No2001-11-092021-11-09Us
US7348362 No2001-06-222021-06-22Us
US7462645 No2001-06-222021-06-22Us
US7465756 No2001-06-222021-06-22Us
US7473710 No2001-06-222021-06-22Us
US7541385 No2001-06-222021-06-22Us
US8110706 No2001-11-092021-11-09Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Vaman Vaishali Haldavanekar, Mangesh Prabhu, Dharmaraj Ramachandra Rao, Rajendra Narayanrao Kankan, “Process for the Synthesis of Arformoterol.” U.S. Patent US20110166237, issued July 07, 2011.

US20110166237
General References
  1. Hanania NA, Donohue JF, Nelson H, Sciarappa K, Goodwin E, Baumgartner RA, Hanrahan JP: The safety and efficacy of arformoterol and formoterol in COPD. COPD. 2010 Feb;7(1):17-31. doi: 10.3109/15412550903499498. [PubMed:20214460 ]
  2. Donohue JF, Hanania NA, Sciarappa KA, Goodwin E, Grogan DR, Baumgartner RA, Hanrahan JP: Arformoterol and salmeterol in the treatment of chronic obstructive pulmonary disease: a one year evaluation of safety and tolerance. Ther Adv Respir Dis. 2008 Apr;2(2):37-48. doi: 10.1177/1753465808089455. [PubMed:19124357 ]
  3. Cazzola M, Matera MG, Lotvall J: Ultra long-acting beta 2-agonists in development for asthma and chronic obstructive pulmonary disease. Expert Opin Investig Drugs. 2005 Jul;14(7):775-83. [PubMed:16022567 ]
  4. Panettieri RA Jr, MacIntyre N, Sims M, Kerwin E, Fogarty C, Noonan M, Claus R, Andrews WT: Comparison of the efficacy and safety of arformoterol 15 microg twice daily and arformoterol 30 microg once daily in COPD: a single-dose, multicenter, randomized, modified-blind, two-way crossover study. Clin Ther. 2009 Aug;31(8):1716-23. doi: 10.1016/j.clinthera.2009.08.012. [PubMed:19808130 ]
  5. Kharidia J, Fogarty CM, Laforce CF, Maier G, Hsu R, Dunnington KM, Curry L, Baumgartner RA, Hanrahan JP: A pharmacokinetic/pharmacodynamic study comparing arformoterol tartrate inhalation solution and racemic formoterol dry powder inhaler in subjects with chronic obstructive pulmonary disease. Pulm Pharmacol Ther. 2008 Aug;21(4):657-62. doi: 10.1016/j.pupt.2008.03.003. Epub 2008 Apr 7. [PubMed:18501650 ]
  6. Baumgartner RA, Hanania NA, Calhoun WJ, Sahn SA, Sciarappa K, Hanrahan JP: Nebulized arformoterol in patients with COPD: a 12-week, multicenter, randomized, double-blind, double-dummy, placebo- and active-controlled trial. Clin Ther. 2007 Feb;29(2):261-78. [PubMed:17472819 ]
External Links
ATC CodesNot Available
AHFS Codes
  • 12:12.08.12
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
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 Arformoterol.
AbirateroneThe metabolism of Arformoterol can be decreased when combined with Abiraterone.
AcebutololAcebutolol may decrease the bronchodilatory activities of Arformoterol.
AlprenololAlprenolol may decrease the bronchodilatory activities of Arformoterol.
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Arformoterol.
AmiodaroneArformoterol may increase the QTc-prolonging activities of Amiodarone.
AmiodaroneThe metabolism of Arformoterol can be decreased when combined with Amiodarone.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Arformoterol.
AnagrelideArformoterol may increase the QTc-prolonging activities of Anagrelide.
AprepitantThe metabolism of Arformoterol can be increased when combined with Aprepitant.
ArmodafinilThe metabolism of Arformoterol can be decreased when combined with Armodafinil.
Arsenic trioxideArformoterol may increase the QTc-prolonging activities of Arsenic trioxide.
ArtemetherArformoterol may increase the QTc-prolonging activities of Artemether.
ArtemetherThe metabolism of Arformoterol can be decreased when combined with Artemether.
AsenapineArformoterol may increase the QTc-prolonging activities of Asenapine.
AtenololAtenolol may decrease the bronchodilatory activities of Arformoterol.
AtomoxetineAtomoxetine may increase the tachycardic activities of Arformoterol.
AtosibanThe risk or severity of adverse effects can be increased when Arformoterol is combined with Atosiban.
AzithromycinArformoterol may increase the QTc-prolonging activities of Azithromycin.
BedaquilineArformoterol may increase the QTc-prolonging activities of Bedaquiline.
BendroflumethiazideArformoterol may increase the hypokalemic activities of Bendroflumethiazide.
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Arformoterol.
BetahistineThe therapeutic efficacy of Arformoterol can be decreased when used in combination with Betahistine.
BetaxololThe metabolism of Arformoterol can be decreased when combined with Betaxolol.
BisoprololBisoprolol may decrease the bronchodilatory activities of Arformoterol.
BopindololBopindolol may decrease the bronchodilatory activities of Arformoterol.
BortezomibThe metabolism of Arformoterol can be decreased when combined with Bortezomib.
BumetanideArformoterol may increase the hypokalemic activities of Bumetanide.
BupranololBupranolol may decrease the bronchodilatory activities of Arformoterol.
BupropionThe metabolism of Arformoterol can be decreased when combined with Bupropion.
CapecitabineThe metabolism of Arformoterol can be decreased when combined with Capecitabine.
CarbamazepineThe metabolism of Arformoterol can be increased when combined with Carbamazepine.
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Arformoterol.
CarteololCarteolol may decrease the bronchodilatory activities of Arformoterol.
CelecoxibThe metabolism of Arformoterol can be decreased when combined with Celecoxib.
CeliprololCeliprolol may decrease the bronchodilatory activities of Arformoterol.
CeritinibThe serum concentration of Arformoterol can be increased when it is combined with Ceritinib.
CeritinibArformoterol may increase the QTc-prolonging activities of Ceritinib.
ChloramphenicolThe metabolism of Arformoterol can be decreased when combined with Chloramphenicol.
ChloroquineArformoterol may increase the QTc-prolonging activities of Chloroquine.
ChloroquineThe metabolism of Arformoterol can be decreased when combined with Chloroquine.
ChlorothiazideArformoterol may increase the hypokalemic activities of Chlorothiazide.
ChlorpromazineArformoterol may increase the QTc-prolonging activities of Chlorpromazine.
ChlorpromazineThe metabolism of Arformoterol can be decreased when combined with Chlorpromazine.
ChlorthalidoneArformoterol may increase the hypokalemic activities of Chlorthalidone.
CholecalciferolThe metabolism of Arformoterol can be decreased when combined with Cholecalciferol.
CimetidineThe metabolism of Arformoterol can be decreased when combined with Cimetidine.
CinacalcetThe metabolism of Arformoterol can be decreased when combined with Cinacalcet.
CiprofloxacinArformoterol may increase the QTc-prolonging activities of Ciprofloxacin.
CisaprideArformoterol may increase the QTc-prolonging activities of Cisapride.
CitalopramArformoterol may increase the QTc-prolonging activities of Citalopram.
CitalopramThe metabolism of Arformoterol can be decreased when combined with Citalopram.
ClarithromycinArformoterol may increase the QTc-prolonging activities of Clarithromycin.
ClemastineThe metabolism of Arformoterol can be decreased when combined with Clemastine.
ClobazamThe metabolism of Arformoterol can be decreased when combined with Clobazam.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Arformoterol.
ClotrimazoleThe metabolism of Arformoterol can be decreased when combined with Clotrimazole.
ClozapineArformoterol may increase the QTc-prolonging activities of Clozapine.
ClozapineThe metabolism of Arformoterol can be decreased when combined with Clozapine.
CobicistatThe serum concentration of Arformoterol can be increased when it is combined with Cobicistat.
CocaineThe metabolism of Arformoterol can be decreased when combined with Cocaine.
CrizotinibArformoterol may increase the QTc-prolonging activities of Crizotinib.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Arformoterol.
CyclosporineThe metabolism of Arformoterol can be decreased when combined with Cyclosporine.
DabrafenibThe serum concentration of Arformoterol can be decreased when it is combined with Dabrafenib.
DarifenacinThe metabolism of Arformoterol can be decreased when combined with Darifenacin.
DarunavirThe serum concentration of Arformoterol can be increased when it is combined with Darunavir.
DelavirdineThe metabolism of Arformoterol can be decreased when combined with Delavirdine.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Arformoterol.
DiphenhydramineThe metabolism of Arformoterol can be decreased when combined with Diphenhydramine.
DisopyramideArformoterol may increase the QTc-prolonging activities of Disopyramide.
DofetilideArformoterol may increase the QTc-prolonging activities of Dofetilide.
DolasetronArformoterol may increase the QTc-prolonging activities of Dolasetron.
DomperidoneArformoterol may increase the QTc-prolonging activities of Domperidone.
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Arformoterol.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Arformoterol.
DronedaroneArformoterol may increase the QTc-prolonging activities of Dronedarone.
DronedaroneThe metabolism of Arformoterol can be decreased when combined with Dronedarone.
DroperidolArformoterol may increase the QTc-prolonging activities of Droperidol.
DuloxetineThe metabolism of Arformoterol can be decreased when combined with Duloxetine.
EfavirenzThe metabolism of Arformoterol can be decreased when combined with Efavirenz.
EliglustatArformoterol may increase the QTc-prolonging activities of Eliglustat.
EliglustatThe metabolism of Arformoterol can be decreased when combined with Eliglustat.
ErythromycinArformoterol may increase the QTc-prolonging activities of Erythromycin.
EscitalopramArformoterol may increase the QTc-prolonging activities of Escitalopram.
Eslicarbazepine acetateThe metabolism of Arformoterol can be decreased when combined with Eslicarbazepine acetate.
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Arformoterol.
EsmololEsmolol may decrease the bronchodilatory activities of Arformoterol.
EsomeprazoleThe metabolism of Arformoterol can be decreased when combined with Esomeprazole.
Etacrynic acidArformoterol may increase the hypokalemic activities of Etacrynic acid.
EtravirineThe metabolism of Arformoterol can be decreased when combined with Etravirine.
FlecainideArformoterol may increase the QTc-prolonging activities of Flecainide.
FloxuridineThe metabolism of Arformoterol can be decreased when combined with Floxuridine.
FluconazoleThe metabolism of Arformoterol can be decreased when combined with Fluconazole.
FluorouracilThe metabolism of Arformoterol can be decreased when combined with Fluorouracil.
FluoxetineArformoterol may increase the QTc-prolonging activities of Fluoxetine.
FluoxetineThe metabolism of Arformoterol can be decreased when combined with Fluoxetine.
FlupentixolArformoterol may increase the QTc-prolonging activities of Flupentixol.
FluvastatinThe metabolism of Arformoterol can be decreased when combined with Fluvastatin.
FluvoxamineThe metabolism of Arformoterol can be decreased when combined with Fluvoxamine.
FosphenytoinThe metabolism of Arformoterol can be increased when combined with Fosphenytoin.
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Arformoterol.
FurosemideArformoterol may increase the hypokalemic activities of Furosemide.
Gadobenic acidArformoterol may increase the QTc-prolonging activities of Gadobenic acid.
GemfibrozilThe metabolism of Arformoterol can be decreased when combined with Gemfibrozil.
GemifloxacinArformoterol may increase the QTc-prolonging activities of Gemifloxacin.
GoserelinArformoterol may increase the QTc-prolonging activities of Goserelin.
GranisetronArformoterol may increase the QTc-prolonging activities of Granisetron.
HaloperidolArformoterol may increase the QTc-prolonging activities of Haloperidol.
HaloperidolThe metabolism of Arformoterol can be decreased when combined with Haloperidol.
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Arformoterol.
HydrochlorothiazideArformoterol may increase the hypokalemic activities of Hydrochlorothiazide.
HydroflumethiazideArformoterol may increase the hypokalemic activities of Hydroflumethiazide.
IbutilideArformoterol may increase the QTc-prolonging activities of Ibutilide.
IloperidoneArformoterol may increase the QTc-prolonging activities of Iloperidone.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Arformoterol.
IndapamideArformoterol may increase the hypokalemic activities of Indapamide.
IndinavirThe metabolism of Arformoterol can be decreased when combined with Indinavir.
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Arformoterol.
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Arformoterol.
IrbesartanThe metabolism of Arformoterol can be decreased when combined with Irbesartan.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Arformoterol.
IsoniazidThe metabolism of Arformoterol can be decreased when combined with Isoniazid.
KetoconazoleThe metabolism of Arformoterol can be decreased when combined with Ketoconazole.
LeflunomideThe metabolism of Arformoterol can be decreased when combined with Leflunomide.
LenvatinibArformoterol may increase the QTc-prolonging activities of Lenvatinib.
LeuprolideArformoterol may increase the QTc-prolonging activities of Leuprolide.
LevofloxacinArformoterol may increase the QTc-prolonging activities of Levofloxacin.
LopinavirArformoterol may increase the QTc-prolonging activities of Lopinavir.
LopinavirThe metabolism of Arformoterol can be decreased when combined with Lopinavir.
LorcaserinThe metabolism of Arformoterol can be decreased when combined with Lorcaserin.
LosartanThe metabolism of Arformoterol can be decreased when combined with Losartan.
LovastatinThe metabolism of Arformoterol can be decreased when combined with Lovastatin.
LuliconazoleThe serum concentration of Arformoterol can be increased when it is combined with Luliconazole.
LumacaftorThe serum concentration of Arformoterol can be decreased when it is combined with Lumacaftor.
LumefantrineArformoterol may increase the QTc-prolonging activities of Lumefantrine.
LumefantrineThe metabolism of Arformoterol can be decreased when combined with Lumefantrine.
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Arformoterol.
MethadoneArformoterol may increase the QTc-prolonging activities of Methadone.
MethadoneThe metabolism of Arformoterol can be decreased when combined with Methadone.
MethotrimeprazineThe metabolism of Arformoterol can be decreased when combined with Methotrimeprazine.
MethyclothiazideArformoterol may increase the hypokalemic activities of Methyclothiazide.
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Arformoterol.
MetolazoneArformoterol may increase the hypokalemic activities of Metolazone.
MetoprololThe metabolism of Arformoterol can be decreased when combined with Metoprolol.
MifepristoneMifepristone may increase the QTc-prolonging activities of Arformoterol.
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Arformoterol.
MirabegronThe metabolism of Arformoterol can be decreased when combined with Mirabegron.
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Arformoterol.
MoclobemideThe metabolism of Arformoterol can be decreased when combined with Moclobemide.
ModafinilThe metabolism of Arformoterol can be decreased when combined with Modafinil.
MoxifloxacinArformoterol may increase the QTc-prolonging activities of Moxifloxacin.
NadololNadolol may decrease the bronchodilatory activities of Arformoterol.
NebivololNebivolol may decrease the bronchodilatory activities of Arformoterol.
NelfinavirThe metabolism of Arformoterol can be decreased when combined with Nelfinavir.
NevirapineThe metabolism of Arformoterol can be decreased when combined with Nevirapine.
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Arformoterol.
NicardipineThe metabolism of Arformoterol can be decreased when combined with Nicardipine.
NicotineThe metabolism of Arformoterol can be decreased when combined with Nicotine.
NilotinibArformoterol may increase the QTc-prolonging activities of Nilotinib.
NilotinibThe metabolism of Arformoterol can be decreased when combined with Nilotinib.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Arformoterol.
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Arformoterol.
OfloxacinArformoterol may increase the QTc-prolonging activities of Ofloxacin.
OmeprazoleThe metabolism of Arformoterol can be decreased when combined with Omeprazole.
OndansetronArformoterol may increase the QTc-prolonging activities of Ondansetron.
OxprenololOxprenolol may decrease the bronchodilatory activities of Arformoterol.
PaliperidoneArformoterol may increase the QTc-prolonging activities of Paliperidone.
PanobinostatArformoterol may increase the QTc-prolonging activities of Panobinostat.
PanobinostatThe metabolism of Arformoterol can be decreased when combined with Panobinostat.
PantoprazoleThe metabolism of Arformoterol can be decreased when combined with Pantoprazole.
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Arformoterol.
ParoxetineThe metabolism of Arformoterol can be decreased when combined with Paroxetine.
PazopanibArformoterol may increase the QTc-prolonging activities of Pazopanib.
Peginterferon alfa-2bThe serum concentration of Arformoterol can be decreased when it is combined with Peginterferon alfa-2b.
PenbutololPenbutolol may decrease the bronchodilatory activities of Arformoterol.
PentamidineArformoterol may increase the QTc-prolonging activities of Pentamidine.
PentobarbitalThe metabolism of Arformoterol can be increased when combined with Pentobarbital.
PerflutrenArformoterol may increase the QTc-prolonging activities of Perflutren.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Arformoterol.
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Arformoterol.
PhenobarbitalThe metabolism of Arformoterol can be increased when combined with Phenobarbital.
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Arformoterol.
PhenytoinThe metabolism of Arformoterol can be increased when combined with Phenytoin.
PimozideArformoterol may increase the QTc-prolonging activities of Pimozide.
PindololPindolol may decrease the bronchodilatory activities of Arformoterol.
PiretanideArformoterol may increase the hypokalemic activities of Piretanide.
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Arformoterol.
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Arformoterol.
PolythiazideArformoterol may increase the hypokalemic activities of Polythiazide.
PrimaquineArformoterol may increase the QTc-prolonging activities of Primaquine.
PrimidoneThe metabolism of Arformoterol can be increased when combined with Primidone.
ProcainamideArformoterol may increase the QTc-prolonging activities of Procainamide.
PromazineArformoterol may increase the QTc-prolonging activities of Promazine.
PromazineThe metabolism of Arformoterol can be decreased when combined with Promazine.
PropafenoneArformoterol may increase the QTc-prolonging activities of Propafenone.
PropranololPropranolol may decrease the bronchodilatory activities of Arformoterol.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Arformoterol.
PyrimethamineThe metabolism of Arformoterol can be decreased when combined with Pyrimethamine.
QuetiapineArformoterol may increase the QTc-prolonging activities of Quetiapine.
QuinethazoneArformoterol may increase the hypokalemic activities of Quinethazone.
QuinidineArformoterol may increase the QTc-prolonging activities of Quinidine.
QuinidineThe metabolism of Arformoterol can be decreased when combined with Quinidine.
QuinineArformoterol may increase the QTc-prolonging activities of Quinine.
QuinineThe metabolism of Arformoterol can be decreased when combined with Quinine.
RanolazineThe metabolism of Arformoterol can be decreased when combined with Ranolazine.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Arformoterol.
RifampicinThe metabolism of Arformoterol can be increased when combined with Rifampicin.
RifapentineThe metabolism of Arformoterol can be increased when combined with Rifapentine.
RitonavirThe metabolism of Arformoterol can be decreased when combined with Ritonavir.
RolapitantThe metabolism of Arformoterol can be decreased when combined with Rolapitant.
RopiniroleThe metabolism of Arformoterol can be decreased when combined with Ropinirole.
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Arformoterol.
SaquinavirArformoterol may increase the QTc-prolonging activities of Saquinavir.
SecobarbitalThe metabolism of Arformoterol can be increased when combined with Secobarbital.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Arformoterol.
SertralineThe metabolism of Arformoterol can be decreased when combined with Sertraline.
SildenafilThe metabolism of Arformoterol can be decreased when combined with Sildenafil.
SorafenibThe metabolism of Arformoterol can be decreased when combined with Sorafenib.
SotalolSotalol may decrease the bronchodilatory activities of Arformoterol.
SotalolArformoterol may increase the QTc-prolonging activities of Sotalol.
StiripentolThe metabolism of Arformoterol can be decreased when combined with Stiripentol.
SulfadiazineThe metabolism of Arformoterol can be decreased when combined with Sulfadiazine.
SulfamethoxazoleThe metabolism of Arformoterol can be decreased when combined with Sulfamethoxazole.
SulfisoxazoleArformoterol may increase the QTc-prolonging activities of Sulfisoxazole.
SulfisoxazoleThe metabolism of Arformoterol can be decreased when combined with Sulfisoxazole.
TelavancinArformoterol may increase the QTc-prolonging activities of Telavancin.
TelithromycinArformoterol may increase the QTc-prolonging activities of Telithromycin.
TerbinafineThe metabolism of Arformoterol can be decreased when combined with Terbinafine.
TetrabenazineArformoterol may increase the QTc-prolonging activities of Tetrabenazine.
ThioridazineArformoterol may increase the QTc-prolonging activities of Thioridazine.
ThioridazineThe metabolism of Arformoterol can be decreased when combined with Thioridazine.
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Arformoterol.
TicagrelorThe metabolism of Arformoterol can be decreased when combined with Ticagrelor.
TiclopidineThe metabolism of Arformoterol can be decreased when combined with Ticlopidine.
TimololTimolol may decrease the bronchodilatory activities of Arformoterol.
TipranavirThe metabolism of Arformoterol can be decreased when combined with Tipranavir.
TolbutamideThe metabolism of Arformoterol can be decreased when combined with Tolbutamide.
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Arformoterol.
TopiramateThe metabolism of Arformoterol can be decreased when combined with Topiramate.
TorasemideArformoterol may increase the hypokalemic activities of Torasemide.
ToremifeneArformoterol may increase the QTc-prolonging activities of Toremifene.
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Arformoterol.
TranylcypromineThe metabolism of Arformoterol can be decreased when combined with Tranylcypromine.
TrichlormethiazideArformoterol may increase the hypokalemic activities of Trichlormethiazide.
TrimethoprimThe metabolism of Arformoterol can be decreased when combined with Trimethoprim.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Arformoterol.
Valproic AcidThe metabolism of Arformoterol can be decreased when combined with Valproic Acid.
ValsartanThe metabolism of Arformoterol can be decreased when combined with Valsartan.
VandetanibArformoterol may increase the QTc-prolonging activities of Vandetanib.
VemurafenibArformoterol may increase the QTc-prolonging activities of Vemurafenib.
VenlafaxineThe metabolism of Arformoterol can be decreased when combined with Venlafaxine.
VoriconazoleThe metabolism of Arformoterol can be decreased when combined with Voriconazole.
ZafirlukastThe metabolism of Arformoterol can be decreased when combined with Zafirlukast.
ZiprasidoneArformoterol may increase the QTc-prolonging activities of Ziprasidone.
ZiprasidoneThe metabolism of Arformoterol can be decreased when combined with Ziprasidone.
ZuclopenthixolArformoterol may increase the QTc-prolonging activities of Zuclopenthixol.
Food InteractionsNot Available

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 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
References
  1. Authors unspecified: Arformoterol: (R,R)-eformoterol, (R,R)-formoterol, arformoterol tartrate, eformoterol-sepracor, formoterol-sepracor, R,R-eformoterol, R,R-formoterol. Drugs R D. 2004;5(1):25-7. [PubMed:14725487 ]
  2. Op't Holt TB: Inhaled beta agonists. Respir Care. 2007 Jul;52(7):820-32. [PubMed:17594727 ]
  3. Matera MG, Cazzola M: ultra-long-acting beta2-adrenoceptor agonists: an emerging therapeutic option for asthma and COPD? Drugs. 2007;67(4):503-15. [PubMed:17352511 ]
  4. Cazzola M, Hanania NA, Matera MG: Arformoterol tartrate in the treatment of COPD. Expert Rev Respir Med. 2010 Apr;4(2):155-62. doi: 10.1586/ers.10.16. [PubMed:20406080 ]
  5. Cazzola M, Matera MG, Lotvall J: Ultra long-acting beta 2-agonists in development for asthma and chronic obstructive pulmonary disease. Expert Opin Investig Drugs. 2005 Jul;14(7):775-83. [PubMed:16022567 ]
  6. Kharidia J, Fogarty CM, Laforce CF, Maier G, Hsu R, Dunnington KM, Curry L, Baumgartner RA, Hanrahan JP: A pharmacokinetic/pharmacodynamic study comparing arformoterol tartrate inhalation solution and racemic formoterol dry powder inhaler in subjects with chronic obstructive pulmonary disease. Pulm Pharmacol Ther. 2008 Aug;21(4):657-62. doi: 10.1016/j.pupt.2008.03.003. Epub 2008 Apr 7. [PubMed:18501650 ]
  7. Baumgartner RA, Hanania NA, Calhoun WJ, Sahn SA, Sciarappa K, Hanrahan JP: Nebulized arformoterol in patients with COPD: a 12-week, multicenter, randomized, double-blind, double-dummy, placebo- and active-controlled trial. Clin Ther. 2007 Feb;29(2):261-78. [PubMed:17472819 ]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
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:
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. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
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 ]
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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 ]
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Drug created on May 16, 2007 14:28 / Updated on September 30, 2016 02:25