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

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H28N2O3
Molecular Weight 392.4907
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDACATEROL

SMILES

CCC1=CC2=C(CC(C2)NC[C@H](O)C3=CC=C(O)C4=C3C=CC(=O)N4)C=C1CC

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
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
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)
n = 59
Health Status: unhealthy
Condition: COPD
Age Group: 43.5 years (range: 12.0–64.0 years)
Sex: M+F
Population Size: 59
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
Health Status: unhealthy
Condition: asthma
Sources:
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)
n = 59
Health Status: unhealthy
Condition: COPD
Age Group: 43.5 years (range: 12.0–64.0 years)
Sex: M+F
Population Size: 59
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)
n = 59
Health Status: unhealthy
Condition: COPD
Age Group: 43.5 years (range: 12.0–64.0 years)
Sex: M+F
Population Size: 59
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)
n = 59
Health Status: unhealthy
Condition: COPD
Age Group: 43.5 years (range: 12.0–64.0 years)
Sex: M+F
Population Size: 59
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)
n = 59
Health Status: unhealthy
Condition: COPD
Age Group: 43.5 years (range: 12.0–64.0 years)
Sex: M+F
Population Size: 59
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
Health Status: unhealthy
Condition: asthma
Sources:
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
ultra-long-acting beta2-adrenoceptor agonists: an emerging therapeutic option for asthma and COPD?
2007
Gateways to clinical trials.
2007 Jan-Feb
Effect of indacaterol, a novel long-acting beta2-agonist, on isolated human bronchi.
2007 Mar
Gateways to clinical trials.
2008 Jan-Feb
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
Gateways to clinical trials.
2009 Apr
Gateways to clinical trials.
2009 Sep
Pharmacogenetic characterization of indacaterol, a novel beta 2-adrenoceptor agonist.
2009 Sep
Indacaterol maleate for the treatment of chronic obstructive pulmonary disease.
2010 Aug
QVA149 demonstrates superior bronchodilation compared with indacaterol or placebo in patients with chronic obstructive pulmonary disease.
2010 Dec
Efficacy and safety of indacaterol 150 microg once-daily in COPD: a double-blind, randomised, 12-week study.
2010 Mar 8
[Indacaterol is a new once-daily beta2-agonist for treatment of COPD].
2010 Nov 22
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
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
5-{(1R)-2-[(5,6-Diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl}-8-hydroxyquinolin-2(1H)-one
Systematic Name English
Indacaterol [WHO-DD]
Common Name English
INDACTEROL
Common Name English
INDACATEROL [VANDF]
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
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NDF-RT N0000175779
Created by admin on Fri Dec 15 17:17:25 GMT 2023 , Edited by admin on Fri Dec 15 17:17:25 GMT 2023
EMA ASSESSMENT REPORTS XOTERNA BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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NCI_THESAURUS C48149
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EMA ASSESSMENT REPORTS ULTIBRO BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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WHO-ATC R03AC18
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WHO-ATC R03AL04
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WHO-VATC QR03AL04
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Code System Code Type Description
DRUG CENTRAL
4183
Created by admin on Fri Dec 15 17:17:25 GMT 2023 , Edited by admin on Fri Dec 15 17:17:25 GMT 2023
PRIMARY
LACTMED
Indacaterol
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PRIMARY
MERCK INDEX
m6240
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PRIMARY Merck Index
SMS_ID
100000093052
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PRIMARY
CHEBI
68575
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PRIMARY
INN
8457
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PRIMARY
DRUG BANK
DB05039
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PRIMARY
WIKIPEDIA
INDACATEROL
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PRIMARY
CAS
312753-06-3
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PRIMARY
PUBCHEM
6918554
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PRIMARY
ChEMBL
CHEMBL1095777
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PRIMARY
RXCUI
1114326
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PRIMARY RxNorm
IUPHAR
7455
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PRIMARY
EPA CompTox
DTXSID90185198
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PRIMARY
FDA UNII
8OR09251MQ
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PRIMARY
NCI_THESAURUS
C81644
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PRIMARY
USAN
UU-171
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PRIMARY
EVMPD
SUB30138
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PRIMARY