Identification

Name
Indacaterol
Accession Number
DB05039
Type
Small Molecule
Groups
Approved
Description

Indacaterol is a novel, ultra-long-acting, rapid onset β(2)-adrenoceptor agonist developed for Novartis for the once-daily management of asthma and chronic obstructive pulmonary disease. It was approved by the European Medicines Agency (EMA) under the trade name Onbrez on November 30, 2009, and by the United States Food and Drug Administration (FDA), under the trade name Arcapta Neohaler, on July 1, 2011. Indacaterol is provided as its maleate salt form. Indacaterol is also a chiral molecule but only the pure R-enantiomer is dispensed.

Structure
Thumb
Synonyms
  • 5-(2-(5,6-Diethylindan-2-ylamino)-1-hydroxyethyl)-8-hydroxy-1H-quinolin-2-one
  • QAB 149
  • QAB-149
  • QAB149
Product Ingredients
IngredientUNIICASInChI Key
Indacaterol Maleate2JEC1ITX7R753498-25-8IREJFXIHXRZFER-PCBAQXHCSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Arcapta NeohalerCapsule75 ug/1Oral; Respiratory (inhalation)Novartis2011-07-01Not applicableUs
Arcapta NeohalerCapsule75 ug/1Oral; Respiratory (inhalation)Sunovion2011-07-01Not applicableUs
Hirobriz BreezhalerCapsule150 μgRespiratory (inhalation)Novartis Europharm Limited2009-11-30Not applicableEu
Hirobriz BreezhalerCapsule300 μgRespiratory (inhalation)Novartis Europharm Limited2009-11-30Not applicableEu
Hirobriz BreezhalerCapsule300 μgRespiratory (inhalation)Novartis Europharm Limited2009-11-30Not applicableEu
Hirobriz BreezhalerCapsule150 μgRespiratory (inhalation)Novartis Europharm Limited2009-11-30Not applicableEu
Hirobriz BreezhalerCapsule150 μgRespiratory (inhalation)Novartis Europharm Limited2009-11-30Not applicableEu
Hirobriz BreezhalerCapsule300 μgRespiratory (inhalation)Novartis Europharm Limited2009-11-30Not applicableEu
Hirobriz BreezhalerCapsule150 μgRespiratory (inhalation)Novartis Europharm Limited2009-11-30Not applicableEu
Hirobriz BreezhalerCapsule300 μgRespiratory (inhalation)Novartis Europharm Limited2009-11-30Not applicableEu
International/Other Brands
Arcapta (Novartis) / Hirobriz / Onbrez (Novartis) / Onbrize
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ultibro BreezhalerIndacaterol (110 mcg) + Glycopyrronium (50 mcg)Capsule; KitRespiratory (inhalation)Novartis2014-03-05Not applicableCanada
Utibron NeohalerIndacaterol Maleate (27.5 ug/1) + Glycopyrronium bromide (15.6 ug/1)CapsuleRespiratory (inhalation)Sunovion2017-04-03Not applicableUs
Utibron NeohalerIndacaterol Maleate (27.5 ug/1) + Glycopyrronium bromide (15.6 ug/1)CapsuleRespiratory (inhalation)Novartis2015-10-29Not applicableUs
Categories
UNII
8OR09251MQ
CAS number
312753-06-3
Weight
Average: 392.4907
Monoisotopic: 392.209992772
Chemical Formula
C24H28N2O3
InChI Key
QZZUEBNBZAPZLX-QFIPXVFZSA-N
InChI
InChI=1S/C24H28N2O3/c1-3-14-9-16-11-18(12-17(16)10-15(14)4-2)25-13-22(28)19-5-7-21(27)24-20(19)6-8-23(29)26-24/h5-10,18,22,25,27-28H,3-4,11-13H2,1-2H3,(H,26,29)/t22-/m0/s1
IUPAC Name
5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-1,2-dihydroquinolin-2-one
SMILES
CCC1=C(CC)C=C2CC(CC2=C1)NC[[email protected]](O)C1=C2C=CC(=O)NC2=C(O)C=C1

Pharmacology

Indication

For the long term, once-daily-dosing maintenance of airflow obstruction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and/or emphysema.

Structured Indications
Pharmacodynamics

Bronchodilator drugs are the foundation for the treatment of chronic obstructive pulmonary disease. The principal inhaled bronchodilator treatments used are β(2) -agonists and anticholinergics, either alone or in combination. Currently available β(2) -agonists are of either short duration and used multiple times/day, or of long duration, which requires twice-daily administration. Indacaterol is considered an ultra-long-acting β(2) -agonist and was recently approved for use in the United States. Its duration of action is approximately 24 hours, allowing for once-daily administration. Furthermore, this chiral compound it is given as the R-enantiomer and acts as a full agonist. Cough was the most commonly reported adverse effect with use of indacaterol. Compared to salmeterol, it has 35% more agonist activity. Cough usually occurred within 15 seconds of inhalation of the drug, lasted around 6 seconds, was not associated with bronchospasm, and did not cause discontinuation of the drug. Otherwise, the drug's safety profile was similar to that of other bronchodilators. [PMID: 22499359]

Mechanism of action

Indacaterol works by stimulating adrenergic beta-2 receptors in the smooth muscle of the airways. This causes relaxation of the muscle, thereby increasing the diameter of the airways, which become constricted in asthma and COPD. It is also long acting due to its high affinity to the lipid raft domains in the airway membrane so it slowly dissociates from the receptors. Indacaterol also has a high intrinsic efficacy so it is also very rapid acting - onset of action occurs within 5 minutes.

The pharmacological effects of beta2-adrenoceptor agonist drugs, including indacaterol, 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 monophosphate). Increased cyclic AMP levels cause relaxation of bronchial smooth muscle. In vitro studies have shown that indacaterol has more than 24-fold greater agonist activity at beta2-receptors compared to beta1-receptors and 20-fold greater agonist activity compared to beta3-receptors. This selectivity profile is similar to formoterol. The clinical significance of these findings is unknown.

TargetActionsOrganism
ABeta-2 adrenergic receptor
agonist
Human
Absorption

The median time to reach peak serum concentrations of indacaterol was approximately 15 minutes after single or repeated inhaled doses. Absolute bioavailability of indacaterol after an inhaled dose was on average 43-45%.

Volume of distribution

After intravenous infusion the volume of distribution (Vz) of indacaterol was 2,361 L to 2,557 L indicating an extensive distribution.

Protein binding

The in vitro human serum and plasma protein binding was 94.1-95.3% and 95.1-96.2%, respectively.

Metabolism

After oral administration of radiolabeled indacaterol, unchanged indacaterol was the main component in serum, accounting for about one third of total drug-related AUC over 24 hours. The monohydroxylated derivative, glucuronide conjugate, and the 8-O-glucuronide were the most prominent metabolites in serum. Other metabolites identified include a diastereomer of the hydroxylated derivative, a N-glucuronide of indacaterol, and C- and N-dealkylated products.

In vitro investigations indicated that UGT1A1 was the only UGT isoform that metabolized indacaterol to the phenolic O-glucuronide. CYP3A4 is the predominant isoenzyme responsible for hydroxylation of indacaterol.

Route of elimination

Renal clearance plays a minor role (about 2 to 6% of systemic clearance) in the elimination of systemically available indacaterol. In a human ADME study where indacaterol was given orally, the fecal route of excretion was dominant over the urinary route. Indacaterol was excreted into human feces primarily as unchanged parent drug (54% of the dose) and, to a lesser extent, hydroxylated indacaterol metabolites (23% of the dose).

Half life

Indacaterol serum concentrations declined in a multi-phasic manner with an average terminal half-life ranging from 45.5 to 126 hours. The effective half-life, calculated from the accumulation of indacaterol after repeated dosing with once daily doses between 75 mcg and 600 mcg ranged from 40 to 56 hours which is consistent with the observed time-to-steady state of approximately 12-15 days.

Clearance

Renal clearance of indacaterol is, on average, between 0.46 and 1.2 L/h. Serum clearance of indacaterol is 18.8 L/h to 23.3 L/h.

Toxicity

The expected signs and symptoms associated with overdosage of indacaterol are those of excessive beta-adrenergic stimulation and occurrence or exaggeration of any of the signs and symptoms, e.g., angina, hypertension or hypotension, tachycardia, with rates up to 200 bpm, arrhythmias, nervousness, headache, tremor, dry mouth, palpitation, muscle cramps, nausea, dizziness, fatigue, malaise, hypokalemia, hyperglycemia, metabolic acidosis and insomnia. As with all inhaled sympathomimetic medications, cardiac arrest and even death may be associated with an overdose of indacaterol.

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

Interactions

Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneIndacaterol may increase the hypokalemic activities of 16-Bromoepiandrosterone.Investigational
19-norandrostenedioneIndacaterol may increase the hypokalemic activities of 19-norandrostenedione.Experimental, Illicit
5-androstenedioneIndacaterol may increase the hypokalemic activities of 5-androstenedione.Experimental, Illicit
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 Indacaterol.Experimental
AlclometasoneIndacaterol may increase the hypokalemic activities of Alclometasone.Approved
AldosteroneIndacaterol may increase the hypokalemic activities of Aldosterone.Experimental, Investigational
AlprenololAlprenolol may decrease the bronchodilatory activities of Indacaterol.Approved, Withdrawn
Ambroxol acefyllinateThe risk or severity of adverse effects can be increased when Ambroxol acefyllinate is combined with Indacaterol.Experimental, Investigational
AmcinonideIndacaterol may increase the hypokalemic activities of Amcinonide.Approved
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Indacaterol.Illicit, Withdrawn
AmiodaroneThe metabolism of Indacaterol can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Indacaterol.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Indacaterol.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Indacaterol.Approved, Illicit
AndrostenedioneIndacaterol may increase the hypokalemic activities of Androstenedione.Experimental, Illicit
AnecortaveIndacaterol may increase the hypokalemic activities of Anecortave.Investigational
anecortave acetateIndacaterol may increase the hypokalemic activities of anecortave acetate.Investigational
AprepitantThe serum concentration of Indacaterol can be increased when it is combined with Aprepitant.Approved, Investigational
AtamestaneIndacaterol may increase the hypokalemic activities of Atamestane.Investigational
AtazanavirThe metabolism of Indacaterol can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineAtomoxetine may increase the tachycardic activities of Indacaterol.Approved
AtosibanThe risk or severity of adverse effects can be increased when Indacaterol is combined with Atosiban.Approved, Investigational
Beclomethasone dipropionateIndacaterol may increase the hypokalemic activities of Beclomethasone dipropionate.Approved, Investigational
BendroflumethiazideIndacaterol may increase the hypokalemic activities of Bendroflumethiazide.Approved
BetahistineThe therapeutic efficacy of Indacaterol can be decreased when used in combination with Betahistine.Approved
BetamethasoneIndacaterol may increase the hypokalemic activities of Betamethasone.Approved, Vet Approved
BoceprevirThe metabolism of Indacaterol can be decreased when combined with Boceprevir.Approved, Withdrawn
BopindololBopindolol may decrease the bronchodilatory activities of Indacaterol.Approved
BortezomibThe metabolism of Indacaterol can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Indacaterol can be decreased when it is combined with Bosentan.Approved, Investigational
BrofaromineThe risk or severity of adverse effects can be increased when Brofaromine is combined with Indacaterol.Experimental
BudesonideIndacaterol may increase the hypokalemic activities of Budesonide.Approved
BumetanideIndacaterol may increase the hypokalemic activities of Bumetanide.Approved
BupranololBupranolol may decrease the bronchodilatory activities of Indacaterol.Approved
CarbamazepineThe metabolism of Indacaterol can be increased when combined with Carbamazepine.Approved, Investigational
CarteololCarteolol may decrease the bronchodilatory activities of Indacaterol.Approved
CeritinibThe serum concentration of Indacaterol can be increased when it is combined with Ceritinib.Approved
ChlorothiazideIndacaterol may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorthalidoneIndacaterol may increase the hypokalemic activities of Chlorthalidone.Approved
CiclesonideIndacaterol may increase the hypokalemic activities of Ciclesonide.Approved, Investigational
ClarithromycinThe metabolism of Indacaterol can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Indacaterol can be decreased when combined with Clemastine.Approved
ClobetasolIndacaterol may increase the hypokalemic activities of Clobetasol.Investigational
Clobetasol propionateIndacaterol may increase the hypokalemic activities of Clobetasol propionate.Approved
ClobetasoneIndacaterol may increase the hypokalemic activities of Clobetasone.Approved
ClocortoloneIndacaterol may increase the hypokalemic activities of Clocortolone.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Indacaterol.Approved, Vet Approved
CloranololCloranolol may decrease the bronchodilatory activities of Indacaterol.Experimental
ClotrimazoleThe metabolism of Indacaterol can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Indacaterol can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Indacaterol.Approved, Investigational
Cortexolone 17α-propionateIndacaterol may increase the hypokalemic activities of Cortexolone 17α-propionate.Investigational
CorticosteroneIndacaterol may increase the hypokalemic activities of Corticosterone.Experimental
Cortisone acetateIndacaterol may increase the hypokalemic activities of Cortisone acetate.Approved
CrizotinibThe metabolism of Indacaterol can be decreased when combined with Crizotinib.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Indacaterol.Approved
CyclopenthiazideIndacaterol may increase the hypokalemic activities of Cyclopenthiazide.Experimental
CyclosporineThe metabolism of Indacaterol can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Indacaterol can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Indacaterol can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Indacaterol can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Indacaterol can be decreased when it is combined with Deferasirox.Approved, Investigational
DeflazacortIndacaterol may increase the hypokalemic activities of Deflazacort.Approved, Investigational
DelavirdineThe metabolism of Indacaterol can be decreased when combined with Delavirdine.Approved
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Indacaterol.Approved
DesonideIndacaterol may increase the hypokalemic activities of Desonide.Approved, Investigational
DesoximetasoneIndacaterol may increase the hypokalemic activities of Desoximetasone.Approved
Desoxycorticosterone acetateIndacaterol may increase the hypokalemic activities of Desoxycorticosterone acetate.Approved
Desoxycorticosterone PivalateIndacaterol may increase the hypokalemic activities of Desoxycorticosterone Pivalate.Experimental, Vet Approved
DexamethasoneIndacaterol may increase the hypokalemic activities of Dexamethasone.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateIndacaterol may increase the hypokalemic activities of Dexamethasone isonicotinate.Vet Approved
DibenzepinThe risk or severity of adverse effects can be increased when Dibenzepin is combined with Indacaterol.Experimental
DiflorasoneIndacaterol may increase the hypokalemic activities of Diflorasone.Approved
DifluocortoloneIndacaterol may increase the hypokalemic activities of Difluocortolone.Approved, Investigational, Withdrawn
DifluprednateIndacaterol may increase the hypokalemic activities of Difluprednate.Approved
DihydroergotamineThe metabolism of Indacaterol can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Indacaterol can be decreased when combined with Diltiazem.Approved
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Indacaterol.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Indacaterol.Approved
DoxycyclineThe metabolism of Indacaterol can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Indacaterol can be decreased when combined with Dronedarone.Approved
EnzalutamideThe serum concentration of Indacaterol can be decreased when it is combined with Enzalutamide.Approved
EquileninIndacaterol may increase the hypokalemic activities of Equilenin.Experimental
EquilinIndacaterol may increase the hypokalemic activities of Equilin.Approved
ErythromycinThe metabolism of Indacaterol can be decreased when combined with Erythromycin.Approved, Vet Approved
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Indacaterol.Investigational
EstroneIndacaterol may increase the hypokalemic activities of Estrone.Approved
Estrone sulfateIndacaterol may increase the hypokalemic activities of Estrone sulfate.Approved
Etacrynic acidIndacaterol may increase the hypokalemic activities of Etacrynic acid.Approved
FluasteroneIndacaterol may increase the hypokalemic activities of Fluasterone.Investigational
FluconazoleThe metabolism of Indacaterol can be decreased when combined with Fluconazole.Approved
FludrocortisoneIndacaterol may increase the hypokalemic activities of Fludrocortisone.Approved
FlumethasoneIndacaterol may increase the hypokalemic activities of Flumethasone.Approved, Vet Approved
FlunisolideIndacaterol may increase the hypokalemic activities of Flunisolide.Approved, Investigational
Fluocinolone AcetonideIndacaterol may increase the hypokalemic activities of Fluocinolone Acetonide.Approved, Investigational, Vet Approved
FluocinonideIndacaterol may increase the hypokalemic activities of Fluocinonide.Approved, Investigational
FluocortoloneIndacaterol may increase the hypokalemic activities of Fluocortolone.Approved, Withdrawn
FluorometholoneIndacaterol may increase the hypokalemic activities of Fluorometholone.Approved
FluprednideneIndacaterol may increase the hypokalemic activities of Fluprednidene.Approved, Withdrawn
FluprednisoloneIndacaterol may increase the hypokalemic activities of Fluprednisolone.Approved
FlurandrenolideIndacaterol may increase the hypokalemic activities of Flurandrenolide.Approved
Fluticasone furoateIndacaterol may increase the hypokalemic activities of Fluticasone furoate.Approved
Fluticasone propionateIndacaterol may increase the hypokalemic activities of Fluticasone propionate.Approved
FluvoxamineThe metabolism of Indacaterol can be decreased when combined with Fluvoxamine.Approved, Investigational
FormestaneIndacaterol may increase the hypokalemic activities of Formestane.Approved, Investigational, Withdrawn
FosamprenavirThe metabolism of Indacaterol can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Indacaterol can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Indacaterol can be increased when combined with Fosphenytoin.Approved
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Indacaterol.Approved, Investigational, Vet Approved
FurosemideIndacaterol may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
Fusidic AcidThe serum concentration of Indacaterol can be increased when it is combined with Fusidic Acid.Approved
HalcinonideIndacaterol may increase the hypokalemic activities of Halcinonide.Approved, Investigational, Withdrawn
HarmalineThe risk or severity of adverse effects can be increased when Harmaline is combined with Indacaterol.Experimental
HE3286Indacaterol may increase the hypokalemic activities of HE3286.Investigational
HydrochlorothiazideIndacaterol may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydrocortisoneIndacaterol may increase the hypokalemic activities of Hydrocortisone.Approved, Vet Approved
HydroflumethiazideIndacaterol may increase the hypokalemic activities of Hydroflumethiazide.Approved, Investigational
IdelalisibThe metabolism of Indacaterol can be decreased when combined with Idelalisib.Approved
ImatinibThe metabolism of Indacaterol can be decreased when combined with Imatinib.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Indacaterol.Approved
IndapamideIndacaterol may increase the hypokalemic activities of Indapamide.Approved
IndinavirThe metabolism of Indacaterol can be decreased when combined with Indinavir.Approved
IprindoleThe risk or severity of adverse effects can be increased when Iprindole is combined with Indacaterol.Experimental
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Indacaterol.Withdrawn
IsavuconazoniumThe metabolism of Indacaterol can be decreased when combined with Isavuconazonium.Approved, Investigational
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Indacaterol.Approved
IsradipineThe metabolism of Indacaterol can be decreased when combined with Isradipine.Approved
IstaroximeIndacaterol may increase the hypokalemic activities of Istaroxime.Investigational
ItraconazoleThe metabolism of Indacaterol can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Indacaterol can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Indacaterol can be decreased when combined with Ketoconazole.Approved, Investigational
LofepramineThe risk or severity of adverse effects can be increased when Lofepramine is combined with Indacaterol.Experimental
LopinavirThe metabolism of Indacaterol can be decreased when combined with Lopinavir.Approved
LorpiprazoleThe serum concentration of Indacaterol can be increased when it is combined with Lorpiprazole.Approved
LoteprednolIndacaterol may increase the hypokalemic activities of Loteprednol.Approved
LovastatinThe metabolism of Indacaterol can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Indacaterol can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Indacaterol can be decreased when it is combined with Lumacaftor.Approved
ME-609Indacaterol may increase the hypokalemic activities of ME-609.Investigational
MedrysoneIndacaterol may increase the hypokalemic activities of Medrysone.Approved
MelengestrolIndacaterol may increase the hypokalemic activities of Melengestrol.Vet Approved
MepindololMepindolol may decrease the bronchodilatory activities of Indacaterol.Experimental
MethyclothiazideIndacaterol may increase the hypokalemic activities of Methyclothiazide.Approved
MethylprednisoloneIndacaterol may increase the hypokalemic activities of Methylprednisolone.Approved, Vet Approved
MetolazoneIndacaterol may increase the hypokalemic activities of Metolazone.Approved
MifepristoneThe serum concentration of Indacaterol can be increased when it is combined with Mifepristone.Approved, Investigational
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Indacaterol.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Indacaterol.Approved
MitotaneThe serum concentration of Indacaterol can be decreased when it is combined with Mitotane.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Indacaterol.Approved
MometasoneIndacaterol may increase the hypokalemic activities of Mometasone.Approved, Vet Approved
NCX 1022Indacaterol may increase the hypokalemic activities of NCX 1022.Investigational
NefazodoneThe metabolism of Indacaterol can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Indacaterol can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Indacaterol can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Indacaterol can be increased when combined with Nevirapine.Approved
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Indacaterol.Withdrawn
NilotinibThe metabolism of Indacaterol can be decreased when combined with Nilotinib.Approved, Investigational
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Indacaterol.Approved
OlaparibThe metabolism of Indacaterol can be decreased when combined with Olaparib.Approved
Oleoyl-estroneIndacaterol may increase the hypokalemic activities of Oleoyl-estrone.Investigational
OpipramolThe risk or severity of adverse effects can be increased when Opipramol is combined with Indacaterol.Investigational
OsimertinibThe serum concentration of Indacaterol can be increased when it is combined with Osimertinib.Approved
OxprenololOxprenolol may decrease the bronchodilatory activities of Indacaterol.Approved
PalbociclibThe serum concentration of Indacaterol can be increased when it is combined with Palbociclib.Approved
ParamethasoneIndacaterol may increase the hypokalemic activities of Paramethasone.Approved
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Indacaterol.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Indacaterol.Approved, Investigational
PentobarbitalThe metabolism of Indacaterol can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Indacaterol.Approved
PhenobarbitalThe metabolism of Indacaterol can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Indacaterol can be increased when combined with Phenytoin.Approved, Vet Approved
PiretanideIndacaterol may increase the hypokalemic activities of Piretanide.Experimental
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Indacaterol.Approved
PolythiazideIndacaterol may increase the hypokalemic activities of Polythiazide.Approved
PosaconazoleThe metabolism of Indacaterol can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrasteroneIndacaterol may increase the hypokalemic activities of Prasterone.Approved, Nutraceutical
Prasterone sulfateIndacaterol may increase the hypokalemic activities of Prasterone sulfate.Investigational
PrednicarbateIndacaterol may increase the hypokalemic activities of Prednicarbate.Approved
PrednisoloneIndacaterol may increase the hypokalemic activities of Prednisolone.Approved, Vet Approved
PrednisoneIndacaterol may increase the hypokalemic activities of Prednisone.Approved, Vet Approved
PregnenoloneIndacaterol may increase the hypokalemic activities of Pregnenolone.Experimental, Investigational
PrimidoneThe metabolism of Indacaterol can be increased when combined with Primidone.Approved, Vet Approved
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Indacaterol.Approved
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Indacaterol.Approved
QuinethazoneIndacaterol may increase the hypokalemic activities of Quinethazone.Approved
RanolazineThe serum concentration of Indacaterol can be increased when it is combined with Ranolazine.Approved, Investigational
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Indacaterol.Approved
RifabutinThe metabolism of Indacaterol can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Indacaterol can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Indacaterol can be increased when combined with Rifapentine.Approved
RimexoloneIndacaterol may increase the hypokalemic activities of Rimexolone.Approved
RucaparibThe metabolism of Indacaterol can be decreased when combined with Rucaparib.Approved, Investigational
SaquinavirThe metabolism of Indacaterol can be decreased when combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Indacaterol can be decreased when used in combination with Sarilumab.Approved
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Indacaterol.Approved, Investigational, Vet Approved
SildenafilThe metabolism of Indacaterol can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Indacaterol can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Indacaterol can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Indacaterol can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Indacaterol can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Indacaterol can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Indacaterol can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Indacaterol can be decreased when combined with Telithromycin.Approved
TertatololTertatolol may decrease the bronchodilatory activities of Indacaterol.Experimental
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Indacaterol.Approved, Investigational
TiclopidineThe metabolism of Indacaterol can be decreased when combined with Ticlopidine.Approved
TixocortolIndacaterol may increase the hypokalemic activities of Tixocortol.Approved, Withdrawn
TocilizumabThe serum concentration of Indacaterol can be decreased when it is combined with Tocilizumab.Approved
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Indacaterol.Approved
TorasemideIndacaterol may increase the hypokalemic activities of Torasemide.Approved
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Indacaterol.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Indacaterol.Approved
TriamcinoloneIndacaterol may increase the hypokalemic activities of Triamcinolone.Approved, Vet Approved
TrichlormethiazideIndacaterol may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Indacaterol.Approved
UlobetasolIndacaterol may increase the hypokalemic activities of Ulobetasol.Approved
VemurafenibThe serum concentration of Indacaterol can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Indacaterol can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Indacaterol can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Indacaterol can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Indacaterol can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not Available

References

General References
  1. Naline E, Trifilieff A, Fairhurst RA, Advenier C, Molimard M: Effect of indacaterol, a novel long-acting beta2-agonist, on isolated human bronchi. Eur Respir J. 2007 Mar;29(3):575-81. Epub 2006 Nov 29. [PubMed:17135231]
  2. Kagan M, Dain J, Peng L, Reynolds C: Metabolism and pharmacokinetics of indacaterol in humans. Drug Metab Dispos. 2012 Sep;40(9):1712-22. doi: 10.1124/dmd.112.046151. Epub 2012 May 30. [PubMed:22648561]
  3. Reid DJ, Pham NT: Emerging Therapeutic Options for the Management of COPD. Clin Med Insights Circ Respir Pulm Med. 2013 Apr 9;7:7-15. doi: 10.4137/CCRPM.S8140. Print 2013. [PubMed:23641160]
External Links
Human Metabolome Database
HMDB0015608
KEGG Drug
D09318
PubChem Compound
6918554
PubChem Substance
175426936
ChemSpider
5293751
BindingDB
50318159
ChEBI
68575
ChEMBL
CHEMBL1095777
PharmGKB
PA165958348
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Indacaterol
ATC Codes
R03AL04 — Indacaterol and glycopyrronium bromideR03AC18 — Indacaterol
AHFS Codes
  • 12:12.08.12 — Selective Beta 2-adrenergic Agonists
FDA label
Download (360 KB)
MSDS
Download (479 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAsthma (Part 1) / COPD (Part 2)1
1CompletedTreatmentAsthma Bronchial1
1CompletedTreatmentAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)1
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Healthy Volunteers1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHepatic Insufficiency1
1, 2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2CompletedSupportive CareChronic Obstructive Pulmonary Disease (COPD)1
2CompletedTreatmentAsthma Bronchial7
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)8
2CompletedTreatmentPersistent Asthma1
2RecruitingTreatmentAsthma Bronchial1
2, 3CompletedTreatmentAsthma Bronchial1
2, 3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Lung Diseases, Obstructive / Pulmonary Disease, Chronic Obstructive2
3CompletedTreatmentAsthma Bronchial2
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)32
3CompletedTreatmentChronic Obstructive Pulmonary Disease: COPD1
3CompletedTreatmentPatients With Moderate-to-severe COPD With Destroyed Lung by Tuberculosis1
3CompletedTreatmentPulmonary Disease, Chronic Obstructive1
3RecruitingTreatmentCOPD (Chronic Obstructive Pulmonary Disease)1
3RecruitingTreatmentHeart Failure, Unspecified1
4CompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD) / Hyperinflation / Right Cardiac Failure1
4CompletedTreatmentAsthma Bronchial2
4CompletedTreatmentChronic Lung Diseases / Chronic Obstructive Pulmonary Disease (COPD) / Dyspnea / Hypoxemia / Tachycardia1
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)11
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Healthy Volunteers1
4Not Yet RecruitingNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
4Not Yet RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)3
4WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)2
Not AvailableActive Not RecruitingNot AvailablePulmonary Disease, Chronic Obstructive1
Not AvailableCompletedNot AvailableChronic Obstructive Pulmonary Disease (COPD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CapsuleOral; Respiratory (inhalation)75 ug/1
CapsuleRespiratory (inhalation)75 mcg
CapsuleRespiratory (inhalation)150 μg
CapsuleRespiratory (inhalation)300 μg
Capsule; kitRespiratory (inhalation)
CapsuleRespiratory (inhalation)
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6878721No2000-10-102020-10-10Us
US8067437No2000-06-022020-06-02Us
US8658673No2000-06-022020-06-02Us
US8796307No2000-06-022020-06-02Us
US8479730No2008-10-112028-10-11Us
US7229607No2001-04-092021-04-09Us
US7820694No2000-06-022020-06-02Us
US8029768No2001-04-092021-04-09Us
US8283362No2000-06-022020-06-02Us
US7736670No2001-06-272021-06-27Us
US8435567No2001-06-272021-06-27Us
US8303991No2001-06-272021-06-27Us
US8956661No2001-06-272021-06-27Us
US8580306No2001-06-272021-06-27Us
US6582678No1998-04-242018-04-24Us
US8182838No2008-10-202028-10-20Us
US6521260No1996-01-312016-01-31Us
US8048451No2001-06-272021-06-27Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)195-202°C with decompositionNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00798 mg/mLALOGPS
logP3.31ALOGPS
logP3.26ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)8.51ChemAxon
pKa (Strongest Basic)9.71ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area81.59 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity118.1 m3·mol-1ChemAxon
Polarizability44.96 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9963
Blood Brain Barrier+0.5
Caco-2 permeable-0.6288
P-glycoprotein substrateSubstrate0.6953
P-glycoprotein inhibitor INon-inhibitor0.9284
P-glycoprotein inhibitor IINon-inhibitor0.9178
Renal organic cation transporterNon-inhibitor0.8838
CYP450 2C9 substrateNon-substrate0.8148
CYP450 2D6 substrateNon-substrate0.6907
CYP450 3A4 substrateSubstrate0.5896
CYP450 1A2 substrateInhibitor0.553
CYP450 2C9 inhibitorNon-inhibitor0.56
CYP450 2D6 inhibitorNon-inhibitor0.8547
CYP450 2C19 inhibitorNon-inhibitor0.5581
CYP450 3A4 inhibitorNon-inhibitor0.6546
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5888
Ames testNon AMES toxic0.7577
CarcinogenicityNon-carcinogens0.8559
BiodegradationNot ready biodegradable0.9856
Rat acute toxicity2.6531 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9657
hERG inhibition (predictor II)Inhibitor0.6406
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 hydroxyquinolones. These are compounds containing a quinoline moiety bearing a hydroxyl group and a ketone. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinolones and derivatives
Direct Parent
Hydroxyquinolones
Alternative Parents
8-hydroxyquinolines / Hydroxyquinolines / Hydroquinolones / Hydroquinolines / Indanes / 1-hydroxy-2-unsubstituted benzenoids / Pyridinones / Aralkylamines / Heteroaromatic compounds / 1,2-aminoalcohols
show 8 more
Substituents
Hydroxyquinolone / Dihydroquinolone / Hydroxyquinoline / 8-hydroxyquinoline / Dihydroquinoline / Indane / 1-hydroxy-2-unsubstituted benzenoid / Pyridinone / Aralkylamine / Benzenoid
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
secondary alcohol, secondary amino compound, indanes, quinolone, monohydroxyquinoline (CHEBI:68575)

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. 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]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-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 performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da

Drug created on October 21, 2007 16:23 / Updated on January 19, 2018 10:57