U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H28N2O3
Molecular Weight 392.4916
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDACATEROL

SMILES

CCc1cc2CC(Cc2cc1CC)NC[C@@]([H])(c3ccc(c4c3ccc(n4)O)O)O

InChI

InChIKey=QZZUEBNBZAPZLX-QFIPXVFZSA-N
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

HIDE SMILES / InChI

Molecular Formula C24H28N2O3
Molecular Weight 392.4916
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

TargetsConditions

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

1309478400000
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

1294272000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
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
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
Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Tolerability of indacaterol, a novel once-daily beta2-agonist, in patients with asthma: a randomized, placebo-controlled, 28-day safety study.
2007 Dec
Gateways to clinical trials.
2007 Dec
Efficacy and safety of single therapeutic and supratherapeutic doses of indacaterol versus salmeterol and salbutamol in patients with asthma.
2007 Dec
Safety and tolerability of indacaterol in asthma: a randomized, placebo-controlled 28-day study.
2007 Oct
New approaches to managing asthma: a US perspective.
2008 Apr
Indacaterol provides sustained 24 h bronchodilation on once-daily dosing in asthma: a 7-day dose-ranging study.
2008 Jan
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
Gateways to clinical trials.
2008 Jan-Feb
Bronchodilator efficacy of indacaterol, a novel once-daily beta2-agonist, in patients with persistent asthma.
2008 Jul
A dose-ranging study of indacaterol in obstructive airways disease, with a tiotropium comparison.
2008 Jul
Gateways to clinical trials.
2008 May
Gateways to clinical trials.
2008 Oct
Novel long-acting bronchodilators for COPD and asthma.
2008 Oct
Gateways to clinical trials.
2009 Apr
Bronchodilator effects of indacaterol and formoterol in patients with COPD.
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
[Efficacy and safety of indacaterol - new long-acting beta(2) agonist].
2010
Impact of bronchodilator therapy on exercise tolerance in COPD.
2010 Apr 7
Indacaterol maleate for the treatment of chronic obstructive pulmonary disease.
2010 Aug
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 once-daily is equally effective dosed in the evening or morning in COPD.
2010 Dec
Indacaterol: in chronic obstructive pulmonary disease.
2010 Dec 3
Novel bronchodilators in asthma.
2010 Jan
Once-daily bronchodilators for chronic obstructive pulmonary disease: indacaterol versus tiotropium.
2010 Jul 15
Efficacy of a new once-daily long-acting inhaled beta2-agonist indacaterol versus twice-daily formoterol in COPD.
2010 Jun
Integrating indacaterol dose selection in a clinical study in COPD using an adaptive seamless design.
2010 Jun
Indacaterol: a new once daily long-acting beta(2) adrenoceptor agonist.
2010 Jun 15
Indacaterol for chronic obstructive pulmonary disease (COPD).
2010 Mar
The short, the long and the "ultra-long": why duration of bronchodilator action matters in chronic obstructive pulmonary disease.
2010 Mar
Efficacy and safety of indacaterol 150 microg once-daily in COPD: a double-blind, randomised, 12-week study.
2010 Mar 8
The identification of indacaterol as an ultralong-acting inhaled beta2-adrenoceptor agonist.
2010 May 13
Characteristics of a capsule based dry powder inhaler for the delivery of indacaterol.
2010 Nov
24-h bronchodilator efficacy of single doses of indacaterol in Japanese patients with asthma: a comparison with placebo and salmeterol.
2010 Nov
[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
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)
Substance Class Chemical
Created
by admin
on Sat Jun 26 04:27:40 UTC 2021
Edited
by admin
on Sat Jun 26 04:27:40 UTC 2021
Record UNII
8OR09251MQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDACATEROL
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
ONBREZ
Brand Name English
QAB149
Code English
INDACATEROL [USAN]
Common Name English
INDACTEROL
Common Name English
INDACATEROL [VANDF]
Common Name English
INDACATEROL [WHO-DD]
Common Name English
QAB-149
Code English
INDACATEROL [MART.]
Common Name English
INDACATEROL [MI]
Common Name English
INDACATEROL [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QR03AC18
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
NDF-RT N0000175779
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
EMA ASSESSMENT REPORTS XOTERNA BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
NCI_THESAURUS C48149
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
EMA ASSESSMENT REPORTS ULTIBRO BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
WHO-ATC R03AC18
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
WHO-ATC R03AL04
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
WHO-VATC QR03AL04
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
Code System Code Type Description
DRUG CENTRAL
4183
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
LACTMED
Indacaterol
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
MERCK INDEX
M6240
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY Merck Index
INN
8457
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
DRUG BANK
DB05039
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
WIKIPEDIA
INDACATEROL
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
CAS
312753-06-3
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
PUBCHEM
6918554
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
ChEMBL
CHEMBL1095777
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
RXCUI
1114326
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY RxNorm
IUPHAR
7455
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
EPA CompTox
312753-06-3
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
FDA UNII
8OR09251MQ
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
NCI_THESAURUS
C81644
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
EVMPD
SUB30138
Created by admin on Sat Jun 26 04:27:40 UTC 2021 , Edited by admin on Sat Jun 26 04:27:40 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
In vitro investigations indicated that indacaterol is a low affinity substrate for the efflux pump P-gp.
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
MAJOR
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
MAJOR
BINDER->LIGAND
BINDING
EXCRETED UNCHANGED
URINE
EXCRETED UNCHANGED
FECAL
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC INTRAVENOUS INFUSION

Tmax PHARMACOKINETIC SINGLE OR REPEATED INHALED DOSES