Identification
NameOlodaterol
Accession NumberDB09080
TypeSmall Molecule
GroupsApproved
Description

Olodaterol is a novel, long-acting beta2-adrenergic agonist (LABA) that exerts its pharmacological effect by binding and activating beta2-adrenergic receptors located primarily in the lungs. Beta2-adrenergic receptors are membrane-bound receptors that are normally activated by endogenous epinephrine whose signalling, via a downstream L-type calcium channel interaction, mediates smooth muscle relaxation and bronchodilation. Activation of the receptor stimulates an associated G protein which then activates adenylate cyclase, catalyzing the formation of cyclic adenosine monophosphate (cAMP) and protein kinase A (PKA). Elevation of these two molecules induces bronchodilation by relaxation of airway smooth muscles. It is by this mechanism that olodaterol is used for the treatment of chronic obstructive pulmonary disease (COPD) and the progressive airflow obstruction that is characteristic of it. Treatment with bronchodilators helps to mitigate associated symptoms such as shortness of breath, cough, and sputum production. Single doses of olodaterol have been shown to improve forced expiratory volume in 1 sec (FEV1) for 24 h in patients with COPD, allowing once daily dosing. A once-a-day treatment with a LABA has several advantages over short-acting bronchodilators and twice-daily LABAs including improved convenience and compliance and improved airflow over a 24-hour period. Despite similarities in symptoms, olodaterol is not indicated for the treatment of acute exacerbations of COPD or for the treatment of asthma.

Structure
Thumb
SynonymsNot Available
External IDs BI 1744 / BI-1744 / BI1744
Product Ingredients
IngredientUNIICASInChI KeyDetails
Olodaterol hydrochloride65R445W3V9 869477-96-3KCEHVJZZIGJAAW-FERBBOLQSA-NDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Striverdi RespimatSolution2.5 mcgRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd LteeNot applicableNot applicableCanada
Striverdi RespimatSpray, metered2.5 ug/1Respiratory (inhalation)Boehringer Ingelheim2014-08-01Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Inspiolto RespimatSolutionRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee2015-05-29Not applicableCanada
Stiolto RespimatSpray, meteredRespiratory (inhalation)Boehringer Ingelheim2015-05-21Not applicableUs
Categories
UNIIVD2YSN1AFD
CAS number868049-49-4
WeightAverage: 386.448
Monoisotopic: 386.184171945
Chemical FormulaC21H26N2O5
InChI KeyCOUYJEVMBVSIHV-SFHVURJKSA-N
InChI
InChI=1S/C21H26N2O5/c1-21(2,10-13-4-6-15(27-3)7-5-13)22-11-18(25)16-8-14(24)9-17-20(16)28-12-19(26)23-17/h4-9,18,22,24-25H,10-12H2,1-3H3,(H,23,26)/t18-/m0/s1
IUPAC Name
6-hydroxy-8-[(1R)-1-hydroxy-2-{[1-(4-methoxyphenyl)-2-methylpropan-2-yl]amino}ethyl]-3,4-dihydro-2H-1,4-benzoxazin-3-one
SMILES
COC1=CC=C(CC(C)(C)NC[[email protected]](O)C2=C3OCC(=O)NC3=CC(O)=C2)C=C1
Pharmacology
Indication

Olodaterol is indicated for use in chronic obstructive pulmonary disease (COPD), including chronic bronchitis and/or emphysema. It is not indicated for the treatment of acute exacerbations of COPD or for the treatment of asthma.

Structured Indications
Pharmacodynamics

Olodaterol is a potent agonist of the human beta2-adrenergic receptor in vitro, and is highly selective for this receptor, with much lower levels of activity at the b1- and b3-adrenergic receptors that are commonly expressed on cardiac smooth muscle and adipose tissue, respectively. Binding to the receptor causes smooth muscle relaxation in the lungs and bronchodilation. It has also been shown to potently reverse active bronchoconstriction.

Mechanism of action

Olodaterol is a long-acting beta2-adrenergic agonist (LABA) that exerts its pharmacological effect by binding and activating beta2-adrenergic receptors located primarily in the lungs. Beta2-adrenergic receptors are membrane-bound receptors that are normally activated by endogenous epinephrine whose signalling, via a downstream L-type calcium channel interaction, mediates smooth muscle relaxation and bronchodilation. Activation of the receptor stimulates an associated G protein which then activates adenylate cyclase, catalyzing the formation of cyclic adenosine monophosphate (cAMP) and protein kinase A (PKA). Elevation of these two molecules induces bronchodilation by relaxation of airway smooth muscles.

TargetKindPharmacological actionActionsOrganismUniProt ID
Beta-2 adrenergic receptorProteinyes
agonist
HumanP07550 details
Related Articles
Absorption

Olodaterol reaches maximum plasma concentrations generally within 10 to 20 minutes following drug inhalation. In healthy volunteers, the absolute bioavailability of olodaterol following inhalation was estimated to be approximately 30%, whereas the absolute bioavailability was below 1% when given as an oral solution. Thus, the systemic availability of olodaterol after inhalation is mainly determined by lung absorption, while any swallowed portion of the dose only negligibly contributes to systemic exposure.

Volume of distribution

The volume of distribution is high (1110 L), suggesting extensive distribution into tissue.

Protein binding

In vitro binding of olodaterol to human plasma proteins is independent of concentration and is approximately 60%.

Metabolism

Olodaterol is substantially metabolized by direct glucuronidation and by O-demethylation at the methoxy moiety followed by conjugation. Of the six metabolites identified, only the unconjugated demethylation product binds to beta2-receptors. This metabolite, however, is not detectable in plasma after chronic inhalation of the recommended therapeutic dose. Cytochrome P450 isozymes CYP2C9 and CYP2C8, with negligible contribution of CYP3A4, are involved in the O-demethylation of olodaterol, while uridine diphosphate glycosyl transferase isoforms UGT2B7, UGT1A1, 1A7, and 1A9 were shown to be involved in the formation of olodaterol glucuronides.

SubstrateEnzymesProduct
Olodaterol
O-demethylated olodaterolDetails
Route of elimination

Following intravenous administration of [14C]-labeled olodaterol, 38% of the radioactive dose was recovered in the urine and 53% was recovered in feces. The amount of unchanged olodaterol recovered in the urine after intravenous administration was 19%. Following oral administration, only 9% of olodaterol and/or its metabolites was recovered in urine, while the major portion was recovered in feces (84%).

Half life

The terminal half-life following intravenous administration is 22 hours. The terminal half-life following inhalation in contrast is about 45 hours, indicating that the latter is determined by absorption rather than by elimination processes.

Clearance

Total clearance of olodaterol in healthy volunteers is 872 mL/min, and renal clearance is 173 mL/min.

Toxicity

Adverse drug reactions that occurred at a frequency greater than 2% include nasopharyngitis (11.3%), upper respiratory tract infection (8.2%), bronchitis (4.7%), urinary tract infection (2.5%), cough (4.2%), dizziness (2.3%), rash (2.2%), diarrhea (2.9%), back pain (3.5%), and arthralgia (2.1%).

Affected organismsNot Available
PathwaysNot 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 Olodaterol.Experimental
AbirateroneThe serum concentration of Olodaterol can be increased when it is combined with Abiraterone.Approved
AcebutololAcebutolol may decrease the bronchodilatory activities of Olodaterol.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Olodaterol.Approved, Investigational
AlprenololAlprenolol may decrease the bronchodilatory activities of Olodaterol.Approved, Withdrawn
Ambroxol acefyllinateThe risk or severity of adverse effects can be increased when Ambroxol acefyllinate is combined with Olodaterol.Experimental
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Olodaterol.Illicit, Withdrawn
AminophyllineThe risk or severity of adverse effects can be increased when Aminophylline is combined with Olodaterol.Approved
AmiodaroneOlodaterol 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 Olodaterol.Approved
AnagrelideOlodaterol may increase the QTc-prolonging activities of Anagrelide.Approved
AprepitantThe metabolism of Olodaterol can be increased when combined with Aprepitant.Approved, Investigational
Arsenic trioxideOlodaterol may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherOlodaterol may increase the QTc-prolonging activities of Artemether.Approved
AsenapineOlodaterol may increase the QTc-prolonging activities of Asenapine.Approved
AtenololAtenolol may decrease the bronchodilatory activities of Olodaterol.Approved
AtomoxetineAtomoxetine may increase the tachycardic activities of Olodaterol.Approved
AtosibanThe risk or severity of adverse effects can be increased when Olodaterol is combined with Atosiban.Approved
AzithromycinOlodaterol may increase the QTc-prolonging activities of Azithromycin.Approved
BedaquilineOlodaterol may increase the QTc-prolonging activities of Bedaquiline.Approved
BendroflumethiazideOlodaterol may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Olodaterol.Withdrawn
Benzylpenicilloyl PolylysineOlodaterol may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Olodaterol can be decreased when used in combination with Betahistine.Approved
BetaxololBetaxolol may decrease the bronchodilatory activities of Olodaterol.Approved
BisoprololBisoprolol may decrease the bronchodilatory activities of Olodaterol.Approved
BopindololBopindolol may decrease the bronchodilatory activities of Olodaterol.Approved
BromocriptineBromocriptine may increase the hypertensive activities of Olodaterol.Approved, Investigational
BucindololBucindolol may decrease the vasoconstricting activities of Olodaterol.Investigational
BumetanideOlodaterol may increase the hypokalemic activities of Bumetanide.Approved
BupranololBupranolol may decrease the bronchodilatory activities of Olodaterol.Approved
CabergolineCabergoline may increase the hypertensive activities of Olodaterol.Approved
CaffeineThe risk or severity of adverse effects can be increased when Caffeine is combined with Olodaterol.Approved
CapecitabineThe metabolism of Olodaterol can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Olodaterol can be increased when combined with Carbamazepine.Approved, Investigational
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Olodaterol.Withdrawn
CarteololCarteolol may decrease the bronchodilatory activities of Olodaterol.Approved
CarvedilolCarvedilol may decrease the vasoconstricting activities of Olodaterol.Approved, Investigational
CelecoxibThe metabolism of Olodaterol can be decreased when combined with Celecoxib.Approved, Investigational
CeliprololCeliprolol may decrease the bronchodilatory activities of Olodaterol.Approved, Investigational
CeritinibThe serum concentration of Olodaterol can be increased when it is combined with Ceritinib.Approved
ChloroquineOlodaterol may increase the QTc-prolonging activities of Chloroquine.Approved, Vet Approved
ChlorothiazideOlodaterol may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorpromazineOlodaterol may increase the QTc-prolonging activities of Chlorpromazine.Approved, Vet Approved
ChlorthalidoneOlodaterol may increase the hypokalemic activities of Chlorthalidone.Approved
CholecalciferolThe metabolism of Olodaterol can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CiprofloxacinOlodaterol may increase the QTc-prolonging activities of Ciprofloxacin.Approved, Investigational
CisaprideOlodaterol may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CitalopramOlodaterol may increase the QTc-prolonging activities of Citalopram.Approved
ClarithromycinOlodaterol may increase the QTc-prolonging activities of Clarithromycin.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Olodaterol.Approved, Vet Approved
ClopidogrelThe metabolism of Olodaterol can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe metabolism of Olodaterol can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineOlodaterol may increase the QTc-prolonging activities of Clozapine.Approved
CrizotinibOlodaterol may increase the QTc-prolonging activities of Crizotinib.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Olodaterol.Approved
CyclosporineThe metabolism of Olodaterol can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Olodaterol can be decreased when it is combined with Dabrafenib.Approved
DeferasiroxThe serum concentration of Olodaterol can be increased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Olodaterol can be decreased when combined with Delavirdine.Approved
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Olodaterol.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Olodaterol.Approved
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Olodaterol.Approved
DisopyramideOlodaterol may increase the QTc-prolonging activities of Disopyramide.Approved
DofetilideOlodaterol may increase the QTc-prolonging activities of Dofetilide.Approved
DolasetronOlodaterol may increase the QTc-prolonging activities of Dolasetron.Approved
DomperidoneOlodaterol may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Olodaterol.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Olodaterol.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Olodaterol.Approved
DronedaroneOlodaterol may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolOlodaterol may increase the QTc-prolonging activities of Droperidol.Approved, Vet Approved
DuloxetineDuloxetine may increase the tachycardic activities of Olodaterol.Approved
DyphyllineThe risk or severity of adverse effects can be increased when Dyphylline is combined with Olodaterol.Approved
EfavirenzThe metabolism of Olodaterol can be decreased when combined with Efavirenz.Approved, Investigational
EliglustatOlodaterol may increase the QTc-prolonging activities of Eliglustat.Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Olodaterol.Approved
ErgonovineErgonovine may increase the hypertensive activities of Olodaterol.Approved
ErgotamineErgotamine may increase the hypertensive activities of Olodaterol.Approved
ErythromycinOlodaterol may increase the QTc-prolonging activities of Erythromycin.Approved, Vet Approved
EscitalopramOlodaterol may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Olodaterol.Investigational
EsmololEsmolol may decrease the bronchodilatory activities of Olodaterol.Approved
Etacrynic acidOlodaterol may increase the hypokalemic activities of Etacrynic acid.Approved
EtravirineThe metabolism of Olodaterol can be decreased when combined with Etravirine.Approved
FelodipineThe metabolism of Olodaterol can be decreased when combined with Felodipine.Approved, Investigational
FlecainideOlodaterol may increase the QTc-prolonging activities of Flecainide.Approved, Withdrawn
FloxuridineThe metabolism of Olodaterol can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Olodaterol can be decreased when combined with Fluconazole.Approved
FluorouracilThe metabolism of Olodaterol can be decreased when combined with Fluorouracil.Approved
FluoxetineOlodaterol may increase the QTc-prolonging activities of Fluoxetine.Approved, Vet Approved
FlupentixolOlodaterol may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
FluvastatinThe metabolism of Olodaterol can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Olodaterol can be decreased when combined with Fluvoxamine.Approved, Investigational
FosphenytoinThe metabolism of Olodaterol can be increased when combined with Fosphenytoin.Approved
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Olodaterol.Approved, Vet Approved
FurosemideOlodaterol may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
Gadobenic acidOlodaterol may increase the QTc-prolonging activities of Gadobenic acid.Approved
GemfibrozilThe metabolism of Olodaterol can be decreased when combined with Gemfibrozil.Approved
GemifloxacinOlodaterol may increase the QTc-prolonging activities of Gemifloxacin.Approved, Investigational
GoserelinOlodaterol may increase the QTc-prolonging activities of Goserelin.Approved
GranisetronOlodaterol may increase the QTc-prolonging activities of Granisetron.Approved, Investigational
HaloperidolOlodaterol may increase the QTc-prolonging activities of Haloperidol.Approved
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Olodaterol.Experimental
HydrochlorothiazideOlodaterol may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideOlodaterol may increase the hypokalemic activities of Hydroflumethiazide.Approved
IbutilideOlodaterol may increase the QTc-prolonging activities of Ibutilide.Approved
IloperidoneOlodaterol may increase the QTc-prolonging activities of Iloperidone.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Olodaterol.Approved
IndapamideOlodaterol may increase the hypokalemic activities of Indapamide.Approved
IndinavirThe metabolism of Olodaterol can be decreased when combined with Indinavir.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Olodaterol.Withdrawn
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Olodaterol.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Olodaterol.Withdrawn
IrbesartanThe metabolism of Olodaterol can be decreased when combined with Irbesartan.Approved, Investigational
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Olodaterol.Approved
KetoconazoleThe metabolism of Olodaterol can be decreased when combined with Ketoconazole.Approved, Investigational
LabetalolLabetalol may decrease the vasoconstricting activities of Olodaterol.Approved
LapatinibThe metabolism of Olodaterol can be decreased when combined with Lapatinib.Approved, Investigational
LeflunomideThe metabolism of Olodaterol can be decreased when combined with Leflunomide.Approved, Investigational
LenvatinibOlodaterol may increase the QTc-prolonging activities of Lenvatinib.Approved
LeuprolideOlodaterol may increase the QTc-prolonging activities of Leuprolide.Approved, Investigational
LevofloxacinOlodaterol may increase the QTc-prolonging activities of Levofloxacin.Approved, Investigational
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Olodaterol.Approved
LopinavirOlodaterol may increase the QTc-prolonging activities of Lopinavir.Approved
LosartanThe metabolism of Olodaterol can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Olodaterol can be decreased when combined with Lovastatin.Approved, Investigational
LoxapineThe risk or severity of adverse effects can be increased when Olodaterol is combined with Loxapine.Approved
LumacaftorThe serum concentration of Olodaterol can be increased when it is combined with Lumacaftor.Approved
LumefantrineOlodaterol may increase the QTc-prolonging activities of Lumefantrine.Approved
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Olodaterol.Withdrawn
MethadoneOlodaterol may increase the QTc-prolonging activities of Methadone.Approved
MethyclothiazideOlodaterol 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 Olodaterol.Investigational
MetolazoneOlodaterol may increase the hypokalemic activities of Metolazone.Approved
MetoprololMetoprolol may decrease the bronchodilatory activities of Olodaterol.Approved, Investigational
MifepristoneThe serum concentration of Olodaterol can be increased when it is combined with Mifepristone.Approved, Investigational
MilnacipranMilnacipran may increase the tachycardic activities of Olodaterol.Approved
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Olodaterol.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Olodaterol.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Olodaterol.Approved
MoxifloxacinOlodaterol may increase the QTc-prolonging activities of Moxifloxacin.Approved, Investigational
NadololNadolol may decrease the bronchodilatory activities of Olodaterol.Approved
NebivololNebivolol may decrease the bronchodilatory activities of Olodaterol.Approved, Investigational
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Olodaterol.Withdrawn
NicardipineThe metabolism of Olodaterol can be decreased when combined with Nicardipine.Approved
NilotinibOlodaterol may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Olodaterol.Approved
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Olodaterol.Withdrawn
OfloxacinOlodaterol may increase the QTc-prolonging activities of Ofloxacin.Approved
OmeprazoleThe metabolism of Olodaterol can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OndansetronOlodaterol may increase the QTc-prolonging activities of Ondansetron.Approved
OpipramolThe risk or severity of adverse effects can be increased when Opipramol is combined with Olodaterol.Investigational
OxprenololOxprenolol may decrease the bronchodilatory activities of Olodaterol.Approved
PaliperidoneOlodaterol may increase the QTc-prolonging activities of Paliperidone.Approved
PanobinostatOlodaterol may increase the QTc-prolonging activities of Panobinostat.Approved, Investigational
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Olodaterol.Approved
PazopanibOlodaterol may increase the QTc-prolonging activities of Pazopanib.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Olodaterol.Approved, Investigational
PentamidineOlodaterol may increase the QTc-prolonging activities of Pentamidine.Approved
PerflutrenOlodaterol may increase the QTc-prolonging activities of Perflutren.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Olodaterol.Approved
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Olodaterol.Withdrawn
PhenobarbitalThe metabolism of Olodaterol can be increased when combined with Phenobarbital.Approved
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Olodaterol.Withdrawn
PhenytoinThe metabolism of Olodaterol can be increased when combined with Phenytoin.Approved, Vet Approved
PimozideOlodaterol may increase the QTc-prolonging activities of Pimozide.Approved
PindololPindolol may decrease the bronchodilatory activities of Olodaterol.Approved
PioglitazoneThe metabolism of Olodaterol can be decreased when combined with Pioglitazone.Approved, Investigational
PiretanideOlodaterol may increase the hypokalemic activities of Piretanide.Experimental
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Olodaterol.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Olodaterol.Withdrawn
PolythiazideOlodaterol may increase the hypokalemic activities of Polythiazide.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Olodaterol.Approved
PrimaquineOlodaterol may increase the QTc-prolonging activities of Primaquine.Approved
PrimidoneThe metabolism of Olodaterol can be increased when combined with Primidone.Approved, Vet Approved
ProcainamideOlodaterol may increase the QTc-prolonging activities of Procainamide.Approved
PromazineOlodaterol may increase the QTc-prolonging activities of Promazine.Approved, Vet Approved
PropafenoneOlodaterol may increase the QTc-prolonging activities of Propafenone.Approved
PropranololPropranolol may decrease the bronchodilatory activities of Olodaterol.Approved, Investigational
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Olodaterol.Approved
PyrimethamineThe metabolism of Olodaterol can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuetiapineOlodaterol may increase the QTc-prolonging activities of Quetiapine.Approved
QuinethazoneOlodaterol may increase the hypokalemic activities of Quinethazone.Approved
QuinidineOlodaterol may increase the QTc-prolonging activities of Quinidine.Approved
QuinineOlodaterol may increase the QTc-prolonging activities of Quinine.Approved
RabeprazoleThe metabolism of Olodaterol can be decreased when combined with Rabeprazole.Approved, Investigational
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Olodaterol.Approved
RifampicinThe metabolism of Olodaterol can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Olodaterol can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Olodaterol can be decreased when combined with Ritonavir.Approved, Investigational
RosiglitazoneThe metabolism of Olodaterol can be decreased when combined with Rosiglitazone.Approved, Investigational
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Olodaterol.Withdrawn
SaquinavirOlodaterol may increase the QTc-prolonging activities of Saquinavir.Approved, Investigational
SecobarbitalThe metabolism of Olodaterol 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 Olodaterol.Approved, Investigational, Vet Approved
SildenafilThe metabolism of Olodaterol can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinSilodosin may decrease the vasoconstricting activities of Olodaterol.Approved
SorafenibThe metabolism of Olodaterol can be decreased when combined with Sorafenib.Approved, Investigational
SotalolSotalol may decrease the bronchodilatory activities of Olodaterol.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Olodaterol.Approved
StiripentolThe metabolism of Olodaterol can be decreased when combined with Stiripentol.Approved
SulfadiazineThe metabolism of Olodaterol can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Olodaterol can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Olodaterol can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TamoxifenThe metabolism of Olodaterol can be decreased when combined with Tamoxifen.Approved
TamsulosinTamsulosin may decrease the vasoconstricting activities of Olodaterol.Approved, Investigational
TelavancinOlodaterol may increase the QTc-prolonging activities of Telavancin.Approved
TelithromycinOlodaterol may increase the QTc-prolonging activities of Telithromycin.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Olodaterol.Approved
TeriflunomideThe metabolism of Olodaterol can be decreased when combined with Teriflunomide.Approved
TetrabenazineOlodaterol may increase the QTc-prolonging activities of Tetrabenazine.Approved
TheophyllineThe risk or severity of adverse effects can be increased when Theophylline is combined with Olodaterol.Approved
ThioridazineOlodaterol may increase the QTc-prolonging activities of Thioridazine.Withdrawn
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Olodaterol.Approved
TicagrelorThe metabolism of Olodaterol can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Olodaterol can be decreased when combined with Ticlopidine.Approved
TimololTimolol may decrease the bronchodilatory activities of Olodaterol.Approved
TolbutamideThe metabolism of Olodaterol can be decreased when combined with Tolbutamide.Approved
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Olodaterol.Approved
TorasemideOlodaterol may increase the hypokalemic activities of Torasemide.Approved
ToremifeneOlodaterol 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 Olodaterol.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Olodaterol.Approved
TrichlormethiazideOlodaterol may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinTrimazosin may decrease the vasoconstricting activities of Olodaterol.Experimental
TrimethoprimThe metabolism of Olodaterol 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 Olodaterol.Approved
Valproic AcidThe metabolism of Olodaterol can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Olodaterol can be decreased when combined with Valsartan.Approved, Investigational
VandetanibOlodaterol may increase the QTc-prolonging activities of Vandetanib.Approved
VemurafenibOlodaterol may increase the QTc-prolonging activities of Vemurafenib.Approved
VenlafaxineVenlafaxine may increase the tachycardic activities of Olodaterol.Approved
VoriconazoleThe metabolism of Olodaterol can be decreased when combined with Voriconazole.Approved, Investigational
ZafirlukastThe metabolism of Olodaterol can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneOlodaterol may increase the QTc-prolonging activities of Ziprasidone.Approved
ZuclopenthixolOlodaterol may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Bouyssou T, Casarosa P, Naline E, Pestel S, Konetzki I, Devillier P, Schnapp A: Pharmacological characterization of olodaterol, a novel inhaled beta2-adrenoceptor agonist exerting a 24-hour-long duration of action in preclinical models. J Pharmacol Exp Ther. 2010 Jul;334(1):53-62. doi: 10.1124/jpet.110.167007. Epub 2010 Apr 6. [PubMed:20371707 ]
  2. Bouyssou T, Hoenke C, Rudolf K, Lustenberger P, Pestel S, Sieger P, Lotz R, Heine C, Buttner FH, Schnapp A, Konetzki I: Discovery of olodaterol, a novel inhaled beta2-adrenoceptor agonist with a 24 h bronchodilatory efficacy. Bioorg Med Chem Lett. 2010 Feb 15;20(4):1410-4. doi: 10.1016/j.bmcl.2009.12.087. Epub 2010 Jan 4. [PubMed:20096576 ]
  3. Koch A, Pizzichini E, Hamilton A, Hart L, Korducki L, De Salvo MC, Paggiaro P: Lung function efficacy and symptomatic benefit of olodaterol once daily delivered via Respimat(R) versus placebo and formoterol twice daily in patients with GOLD 2-4 COPD: results from two replicate 48-week studies. Int J Chron Obstruct Pulmon Dis. 2014 Jul 5;9:697-714. doi: 10.2147/COPD.S62502. eCollection 2014. [PubMed:25045258 ]
  4. Gibb A, Yang LP: Olodaterol: first global approval. Drugs. 2013 Nov;73(16):1841-6. doi: 10.1007/s40265-013-0137-9. [PubMed:24158691 ]
  5. Deeks ED: Olodaterol: a review of its use in chronic obstructive pulmonary disease. Drugs. 2015 Apr;75(6):665-73. doi: 10.1007/s40265-015-0371-4. [PubMed:25773742 ]
External Links
ATC CodesR03AL06 — Olodaterol and tiotropium bromideR03AC19 — Olodaterol
AHFS Codes
  • 12:12.08.12
PDB EntriesNot Available
FDA labelDownload (746 KB)
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers / Pulmonary Disease, Chronic Obstructive2
1CompletedTreatmentPulmonary Disease, Chronic Obstructive2
2CompletedTreatmentAsthma Bronchial2
2CompletedTreatmentPulmonary Disease, Chronic Obstructive3
2WithdrawnTreatmentAsthma Bronchial1
3CompletedTreatmentPulmonary Disease, Chronic Obstructive25
4Active Not RecruitingTreatmentPulmonary Disease, Chronic Obstructive1
4CompletedTreatmentPulmonary Disease, Chronic Obstructive1
4Not Yet RecruitingBasic ScienceChronic Obstructive Pulmonary Disease (COPD)2
4Not Yet RecruitingTreatmentPulmonary Disease, Chronic Obstructive1
4RecruitingTreatmentAsthma Bronchial1
4RecruitingTreatmentPulmonary Disease, Chronic Obstructive2
Not AvailableRecruitingNot AvailablePulmonary Disease, Chronic Obstructive2
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
SolutionRespiratory (inhalation)
Spray, meteredRespiratory (inhalation)
SolutionRespiratory (inhalation)2.5 mcg
Spray, meteredRespiratory (inhalation)2.5 ug/1
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
USRE39820 Yes1998-07-302018-07-30Us
US6453795 Yes1997-06-052017-06-05Us
US8733341 Yes2011-04-162031-04-16Us
US9027967 Yes2007-10-012027-10-01Us
US7104470 Yes1997-04-042017-04-04Us
US7246615 Yes1996-12-012016-12-01Us
US7896264 Yes2005-11-262025-11-26Us
US7988001 Yes2002-02-042022-02-04Us
US7802568 Yes1999-08-262019-08-26Us
US6149054 Yes1997-06-162017-06-16Us
US6726124 Yes1997-04-042017-04-04Us
US7396341 Yes2007-04-102027-04-10Us
US6846413 Yes1999-02-282019-02-28Us
US6176442 Yes1996-12-012016-12-01Us
US7837235 Yes2008-09-132028-09-13Us
US5964416 Yes1997-04-042017-04-04Us
US7284474 Yes2005-02-262025-02-26Us
US6977042 Yes1999-02-282019-02-28Us
US6988496 Yes2000-08-232020-08-23Us
US8044046 No2003-11-102023-11-10Us
US8034809 No2005-05-122025-05-12Us
US7220742 No2005-05-122025-05-12Us
US7491719 No2003-11-102023-11-10Us
US7056916 No2003-12-072023-12-07Us
US7727984 No2003-11-102023-11-10Us
US7786111 No2003-11-102023-11-10Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0703 mg/mLALOGPS
logP2.02ALOGPS
logP1.19ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.22ChemAxon
pKa (Strongest Basic)9.84ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area100.05 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity106.9 m3·mol-1ChemAxon
Polarizability41.34 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET featuresNot Available
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazines
Sub ClassBenzoxazinones
Direct ParentBenzoxazinones
Alternative ParentsAmphetamines and derivatives / Benzomorpholines / Phenylpropanes / Phenoxy compounds / Methoxybenzenes / Anisoles / 1-hydroxy-2-unsubstituted benzenoids / Alkyl aryl ethers / Aralkylamines / Secondary carboxylic acid amides
SubstituentsBenzoxazinone / Amphetamine or derivatives / Benzomorpholine / Phenylpropane / Phenoxy compound / Anisole / Phenol ether / Methoxybenzene / Alkyl aryl ether / 1-hydroxy-2-unsubstituted benzenoid
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsaromatic ether, secondary alcohol, phenols, secondary amino compound, benzoxazine (CHEBI:82700 )

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
Uniprot Name:
Beta-2 adrenergic receptor
Molecular Weight:
46458.32 Da
References
  1. Bouyssou T, Casarosa P, Naline E, Pestel S, Konetzki I, Devillier P, Schnapp A: Pharmacological characterization of olodaterol, a novel inhaled beta2-adrenoceptor agonist exerting a 24-hour-long duration of action in preclinical models. J Pharmacol Exp Ther. 2010 Jul;334(1):53-62. doi: 10.1124/jpet.110.167007. Epub 2010 Apr 6. [PubMed:20371707 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
no
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
Uniprot Name:
Cytochrome P450 2C9
Molecular Weight:
55627.365 Da
Kind
Protein
Organism
Human
Pharmacological action
no
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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Uniprot Name:
Cytochrome P450 2C8
Molecular Weight:
55824.275 Da
Drug created on June 26, 2015 12:38 / Updated on September 01, 2017 12:02