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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H28N2O3.C4H4O4
Molecular Weight 508.5629
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of INDACATEROL MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CCC1=C(CC)C=C2CC(CC2=C1)NC[C@H](O)C3=CC=C(O)C4=C3C=CC(=O)N4

InChI

InChIKey=IREJFXIHXRZFER-PCBAQXHCSA-N
InChI=1S/C24H28N2O3.C4H4O4/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;5-3(6)1-2-4(7)8/h5-10,18,22,25,27-28H,3-4,11-13H2,1-2H3,(H,26,29);1-2H,(H,5,6)(H,7,8)/b;2-1-/t22-;/m0./s1

HIDE SMILES / InChI
Indacaterol is an ultra-long-acting beta-adrenoceptor agonist developed by Novartis. It was approved by the European Medicines Agency (EMA) under the trade name Onbrez Breezhaler on November 30, 2009, and by the United States Food and Drug Administration (FDA), under the trade name Arcapta Neohaler, on July 1, 2011. It needs to be taken only once a day, unlike the related drugs formoterol and salmeterol. It is licensed only for the treatment of chronic obstructive pulmonary disease (COPD) (long-term data in patients with asthma are thus far lacking). It is delivered as an aerosol formulation through a dry powder inhaler.

Originator

Curator's Comment: # Novartis

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
76.0 nM [Ki]
91.4 nM [Ki]
76.0 nM [Ki]
91.4 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ARCAPTA NEOHALER

Approved Use

UTIBRONTM NEOHALER® is a combination of indacaterol and glycopyrrolate indicated for the long-term, maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and/or emphysema. Important Limitations of Use: UTIBRON NEOHALER is NOT indicated for the relief of acute bronchospasm or for the treatment of asthma [see Warnings and Precautions (5.1, 5.2)

Launch Date

2011
Primary
ARCAPTA

Approved Use

INDICATIONS AND USAGE. ARCAPTA NEOHALER is a long-acting beta2-adrenergic agonist indicated for: The long term, once-daily maintenance bronchodilator treatment of airflow obstruction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and/or emphysema. Important limitations: ARCAPTA NEOHALER is NOT indicated to treat acute deteriorations of chronic obstructive pulmonary disease. ARCAPTA NEOHALER is NOT indicated for asthma.

Launch Date

2011
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.206 ng/mL
150 μg single, respiratory
dose: 150 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
INDACATEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.518 ng/mL
300 μg single, respiratory
dose: 300 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
INDACATEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.299 ng/mL
150 μg 1 times / day steady-state, respiratory
dose: 150 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
INDACATEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.697 ng/mL
300 μg 1 times / day steady-state, respiratory
dose: 300 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
INDACATEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
339 pg/mL
110 μg single, respiratory
dose: 110 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered: GLYCOPYRROLATE
INDACATEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
528 pg/mL
110 μg 1 times / day steady-state, respiratory
dose: 110 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered: GLYCOPYRROLATE
INDACATEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.974 ng × h/mL
150 μg single, respiratory
dose: 150 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
INDACATEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.43 ng × h/mL
300 μg single, respiratory
dose: 300 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
INDACATEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.51 ng × h/mL
150 μg 1 times / day steady-state, respiratory
dose: 150 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
INDACATEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
6.52 ng × h/mL
300 μg 1 times / day steady-state, respiratory
dose: 300 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
INDACATEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
907 pg × h/mL
110 μg single, respiratory
dose: 110 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered: GLYCOPYRROLATE
INDACATEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2750 pg × h/mL
110 μg 1 times / day steady-state, respiratory
dose: 110 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered: GLYCOPYRROLATE
INDACATEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
116 h
150 μg 1 times / day steady-state, respiratory
dose: 150 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
INDACATEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
118 h
300 μg 1 times / day steady-state, respiratory
dose: 300 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
INDACATEROL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
800 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 800 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 800 ug, 1 times / day
Sources:
unhealthy, 43.5 years (range: 12.0–64.0 years)
Health Status: unhealthy
Age Group: 43.5 years (range: 12.0–64.0 years)
Sex: M+F
Sources:
Disc. AE: Dyspnea, Wheezing...
AEs leading to
discontinuation/dose reduction:
Dyspnea (serious, 1 patient)
Wheezing (serious, 1 patient)
Asthma (moderate, 1 patient)
Cough (moderate, 1 patient)
Sources:
75 ug 1 times / day multiple, respiratory
Dose: 75 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 75 ug, 1 times / day
Sources:
unhealthy
Other AEs: Adverse event...
AEs

AEs

AESignificanceDosePopulation
Asthma moderate, 1 patient
Disc. AE
800 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 800 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 800 ug, 1 times / day
Sources:
unhealthy, 43.5 years (range: 12.0–64.0 years)
Health Status: unhealthy
Age Group: 43.5 years (range: 12.0–64.0 years)
Sex: M+F
Sources:
Cough moderate, 1 patient
Disc. AE
800 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 800 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 800 ug, 1 times / day
Sources:
unhealthy, 43.5 years (range: 12.0–64.0 years)
Health Status: unhealthy
Age Group: 43.5 years (range: 12.0–64.0 years)
Sex: M+F
Sources:
Dyspnea serious, 1 patient
Disc. AE
800 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 800 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 800 ug, 1 times / day
Sources:
unhealthy, 43.5 years (range: 12.0–64.0 years)
Health Status: unhealthy
Age Group: 43.5 years (range: 12.0–64.0 years)
Sex: M+F
Sources:
Wheezing serious, 1 patient
Disc. AE
800 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 800 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 800 ug, 1 times / day
Sources:
unhealthy, 43.5 years (range: 12.0–64.0 years)
Health Status: unhealthy
Age Group: 43.5 years (range: 12.0–64.0 years)
Sex: M+F
Sources:
Adverse event grade 5
75 ug 1 times / day multiple, respiratory
Dose: 75 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 75 ug, 1 times / day
Sources:
unhealthy
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
negligible
negligible
no
no
no
unlikely
unlikely
unlikely
unlikely
weak [IC50 10 uM]
weak [IC50 25 uM]
weak [IC50 25 uM]
weak [IC50 5 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
low
low
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
weak
yes (co-administration study)
Comment: Co-administration of indacaterol with verapamil (P-gp inhibitor) showed 2­ fold increase in indacaterol AUC0-24, and 1.5-fold increase in indacaterol Cmax;
Page: 96.0
yes
weak (pharmacogenomic study)
Comment: Nonsignificant trends toward higher Cmax and AUC0-24 (19% and 20%, respectively) were noted in patients with the (TA)7 genotype
Page: 91.0
yes
yes (co-administration study)
Comment: Co-administration of indacaterol with erythromycin (CYP3A4 inhibitor) showed a 1.4-fold increase in indacaterol AUC0-24, and 1.2-fold increase in indacaterol Cmax; Co-administration of indacaterol with ketoconazole caused a 1.9-fold increase in indacaterol AUC0-24, and 1.3-fold increase in indacaterol Cmax; Co-administration of indacaterol with ritonavir resulted in a 1.7-fold increase in indacaterol AUC0-24 whereas indacaterol Cmax was unaffected.
Page: 91.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Ultra long-acting beta 2-agonists in development for asthma and chronic obstructive pulmonary disease.
2005 Jul
Gateways to clinical trials.
2006 Dec
Gateways to clinical trials.
2006 Jan-Feb
Gateways to clinical trials.
2006 May
Indacaterol Novartis/skyePharma.
2006 May
ultra-long-acting beta2-adrenoceptor agonists: an emerging therapeutic option for asthma and COPD?
2007
Safety, tolerability and efficacy of indacaterol, a novel once-daily beta(2)-agonist, in patients with COPD: a 28-day randomised, placebo controlled clinical trial.
2007
Gateways to clinical trials.
2007 Jan-Feb
Effect of indacaterol, a novel long-acting beta2-agonist, on isolated human bronchi.
2007 Mar
Indacaterol, a novel inhaled beta2-agonist, provides sustained 24-h bronchodilation in asthma.
2007 May
New approaches to managing asthma: a US perspective.
2008 Apr
Efficacy and safety of indacaterol, a new 24-hour beta2-agonist, in patients with asthma: a dose-ranging study.
2008 Dec
Pharmacological characterization of indacaterol, a novel once daily inhaled 2 adrenoceptor agonist, on small airways in human and rat precision-cut lung slices.
2008 Jan
Bronchodilator efficacy of indacaterol, a novel once-daily beta2-agonist, in patients with persistent asthma.
2008 Jul
Gateways to clinical trials.
2008 May
Gateways to clinical trials.
2008 Oct
Gateways to clinical trials.
2009 Apr
Bronchodilator effects of indacaterol and formoterol in patients with COPD.
2009 Dec
Effect of pre-contraction on β-adrenoceptor-mediated relaxation of rat urinary bladder.
2009 Dec
Lipid membrane interactions of indacaterol and salmeterol: do they influence their pharmacological properties?
2009 Dec 8
24-hour bronchodilator efficacy of single doses of indacaterol in subjects with COPD: comparison with placebo and formoterol.
2009 Feb
Gateways to clinical trials.
2009 Jan-Feb
Indacaterol, a novel inhaled, once-daily, long-acting beta2-agonist for the treatment of obstructive airways diseases.
2009 Jul
Indacaterol, A Novel Once Daily Inhaled beta2-Adrenoreceptor Agonist.
2009 Mar 12
Mometasone furoate: an effective anti-inflammatory with a well-defined safety and tolerability profile in the treatment of asthma.
2009 May
24-hour bronchodilator efficacy of single doses of indacaterol in patients with persistent asthma: comparison with placebo and formoterol.
2009 Oct
Gateways to clinical trials.
2009 Sep
Pharmacogenetic characterization of indacaterol, a novel beta 2-adrenoceptor agonist.
2009 Sep
The long-acting beta-adrenoceptor agonist, indacaterol, inhibits IgE-dependent responses of human lung mast cells.
2009 Sep
Cardiovascular safety of QVA149, a combination of Indacaterol and NVA237, in COPD patients.
2010 Dec
QVA149 demonstrates superior bronchodilation compared with indacaterol or placebo in patients with chronic obstructive pulmonary disease.
2010 Dec
Indacaterol: in chronic obstructive pulmonary disease.
2010 Dec 3
Novel bronchodilators in asthma.
2010 Jan
Integrating indacaterol dose selection in a clinical study in COPD using an adaptive seamless design.
2010 Jun
The short, the long and the "ultra-long": why duration of bronchodilator action matters in chronic obstructive pulmonary disease.
2010 Mar
[Indacaterol is a new once-daily beta2-agonist for treatment of COPD].
2010 Nov 22
Long-acting beta-agonists in the management of chronic obstructive pulmonary disease: current and future agents.
2010 Oct 29
Indacaterol provides 24-hour bronchodilation in COPD: a placebo-controlled blinded comparison with tiotropium.
2010 Oct 5
Onset of action of indacaterol in patients with COPD: comparison with salbutamol and salmeterol-fluticasone.
2010 Sep 7
An investigation into the structure-activity relationships associated with the systematic modification of the β(2)-adrenoceptor agonist indacaterol.
2012 Oct 1
Metabolism and pharmacokinetics of indacaterol in humans.
2012 Sep
Emerging Therapeutic Options for the Management of COPD.
2013
An update on LAMA/LABA combinations for COPD.
2017 Jan
Patents

Sample Use Guides

The recommended dosage of Indacaterol is the once-daily inhalation of the contents of one 75 mcg Indacaterol capsule using the NEOHALER inhaler.
Route of Administration: Respiratory
In the isolated tracheal strip preparation, indacaterol, demonstrated concentration-dependent inhibition of electrically induced contraction (EC50= 45 ± 13 nM)
Name Type Language
ARCAPTA NEOHALER
Preferred Name English
INDACATEROL MALEATE
DASH   EMA EPAR   JAN   MART.   MI   ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
INDACTEROL MALEATE
Common Name English
QVA-149 COMPONENT INDACATEROL MALEATE
Common Name English
INDACATEROL (AS MALEATE)
Common Name English
2(1H)-QUINOLINONE, 5-((1R)-2-((5,6-DIETHYL-2,3-DIHYDRO-1H-INDEN-2-YL)AMINO)-1-HYDROXYETHYL )-8-HYDROXY-, (2Z)-2-BUTENEDIOATE (1:1)
Common Name English
QABI49
Code English
INDACATEROL MALEATE [MI]
Common Name English
INDACATEROL MALEATE [EMA EPAR]
Common Name English
INDACATEROL MALEATE [ORANGE BOOK]
Common Name English
ULTIBRO COMPONENT INDACATEROL MALEATE
Brand Name English
INDACATEROL MALEATE [MART.]
Common Name English
QAB149-AFA
Code English
INDACATEROL MALEATE [JAN]
Common Name English
QAB-149-AFA
Code English
INDACATEROL MALEATE [USAN]
Common Name English
5-((1R)-2-((5,6-DIETHYL-2,3-DIHYDRO-1H-INDEN-2-YL)AMINO)-1-HYDROXYETHYL)-8- HYDROXYQUINOLIN-2(1H)-ONE HYDROGEN (2Z)-2-BUTENEDIOATE (SALT)
Common Name English
Indacaterol maleate [WHO-DD]
Common Name English
QVA149 COMPONENT INDACATEROL MALEATE
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS OSLIF BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
EMA ASSESSMENT REPORTS HIROBRIZ BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
NCI_THESAURUS C48149
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
EMA ASSESSMENT REPORTS ULUNAR BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
EMA ASSESSMENT REPORTS ONBREZ BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
Code System Code Type Description
RXCUI
1114325
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
PRIMARY RxNorm
USAN
UU-172
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
PRIMARY
FDA UNII
2JEC1ITX7R
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
PRIMARY
PUBCHEM
9827599
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
PRIMARY
CAS
753498-25-8
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
PRIMARY
SMS_ID
100000092727
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
PRIMARY
CHEBI
68573
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
PRIMARY
DRUG BANK
DBSALT000101
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
PRIMARY
CAS
435273-74-8
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
NON-SPECIFIC STOICHIOMETRY
MERCK INDEX
m6240
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1095777
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
PRIMARY
EVMPD
SUB30300
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
PRIMARY
NCI_THESAURUS
C81640
Created by admin on Mon Mar 31 18:26:36 GMT 2025 , Edited by admin on Mon Mar 31 18:26:36 GMT 2025
PRIMARY