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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

Description

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.

CNS Activity

Originator

Approval Year

Target InfoCondition Info

Condition Info

PMID

PMID

TitleDatePMID
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
In vitro and in vivo pharmacological characterization of 5-[(R)-2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one (indacaterol), a novel inhaled beta(2) adrenoceptor agonist with a 24-h duration of action.
2006 May
Indacaterol Novartis/skyePharma.
2006 May
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
ultra-long-acting beta2-adrenoceptor agonists: an emerging therapeutic option for asthma and COPD?
2007
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
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
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
Efficacy and safety of indacaterol, a new 24-hour beta2-agonist, in patients with asthma: a dose-ranging study.
2008 Dec
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
A dose-ranging study of indacaterol in obstructive airways disease, with a tiotropium comparison.
2008 Jul
Bronchodilator efficacy of indacaterol, a novel once-daily beta2-agonist, in patients with persistent asthma.
2008 Jul
Gateways to clinical trials.
2008 May
A cell-based assay to assess the persistence of action of agonists acting at recombinant human beta(2) adrenoceptors.
2008 Nov-Dec
Gateways to clinical trials.
2008 Oct
Novel long-acting bronchodilators for COPD and asthma.
2008 Oct
Gateways to clinical trials.
2009 Apr
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
The long-acting beta-adrenoceptor agonist, indacaterol, inhibits IgE-dependent responses of human lung mast cells.
2009 Sep
Pharmacogenetic characterization of indacaterol, a novel beta 2-adrenoceptor agonist.
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
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
Novel bronchodilators in asthma.
2010 Jan
Once-daily bronchodilators for chronic obstructive pulmonary disease: indacaterol versus tiotropium.
2010 Jul 15
Indacaterol: a new once daily long-acting beta(2) adrenoceptor agonist.
2010 Jun 15
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
24-h bronchodilator efficacy of single doses of indacaterol in Japanese patients with asthma: a comparison with placebo and salmeterol.
2010 Nov
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
Bronchodilator efficacy of single doses of indacaterol in Japanese patients with COPD: A randomised, double-blind, placebo-controlled trial.
2010 Sep
Efficacy is a contributing factor to the clinical onset of bronchodilation of inhaled beta(2)-adrenoceptor agonists.
2010 Sep
Indacaterol and glycopyrronium versus indacaterol on body plethysmography measurements in COPD-a randomised controlled study.
2017 Jan 11
Patent

Sample Use Guides

In Vivo Use Guide
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 Vitro Use Guide
In the isolated tracheal strip preparation, indacaterol, demonstrated concentration-dependent inhibition of electrically induced contraction (EC50= 45 ± 13 nM)
Name Type Language
INDACATEROL MALEATE
DASH   EMA EPAR   JAN   MART.   MI   ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
INDACTEROL MALEATE
Common Name English
ARCAPTA NEOHALER
Brand 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 [WHO-DD]
Common Name English
INDACATEROL MALEATE [ORANGE BOOK]
Common Name English
INDACATEROL MALEATE [MART.]
Common Name English
INDACATEROL MALEATE COMPONENT OF UTIBRON
Brand 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
Classification Tree Code System Code
EMA ASSESSMENT REPORTS OSLIF BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Tue Mar 06 11:15:37 UTC 2018 , Edited by admin on Tue Mar 06 11:15:37 UTC 2018
EMA ASSESSMENT REPORTS HIROBRIZ BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Tue Mar 06 11:15:37 UTC 2018 , Edited by admin on Tue Mar 06 11:15:37 UTC 2018
EMA ASSESSMENT REPORTS ULUNAR BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Tue Mar 06 11:15:37 UTC 2018 , Edited by admin on Tue Mar 06 11:15:37 UTC 2018
EMA ASSESSMENT REPORTS ONBREZ BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Tue Mar 06 11:15:37 UTC 2018 , Edited by admin on Tue Mar 06 11:15:37 UTC 2018
Code System Code Type Description
RXCUI
1114325
Created by admin on Tue Mar 06 11:15:37 UTC 2018 , Edited by admin on Tue Mar 06 11:15:37 UTC 2018
PRIMARY RxNorm
PUBCHEM
9827599
Created by admin on Tue Mar 06 11:15:37 UTC 2018 , Edited by admin on Tue Mar 06 11:15:37 UTC 2018
PRIMARY SWITZERF
CAS
753498-25-8
Created by admin on Tue Mar 06 11:15:37 UTC 2018 , Edited by admin on Tue Mar 06 11:15:37 UTC 2018
PRIMARY
MERCK INDEX
M6240
Created by admin on Tue Mar 06 11:15:37 UTC 2018 , Edited by admin on Tue Mar 06 11:15:37 UTC 2018
PRIMARY Merck Index
ChEMBL
CHEMBL1095777
Created by admin on Tue Mar 06 11:15:37 UTC 2018 , Edited by admin on Tue Mar 06 11:15:37 UTC 2018
PRIMARY
EVMPD
SUB30300
Created by admin on Tue Mar 06 11:15:37 UTC 2018 , Edited by admin on Tue Mar 06 11:15:37 UTC 2018
PRIMARY
NCI_THESAURUS
C81640
Created by admin on Tue Mar 06 11:15:37 UTC 2018 , Edited by admin on Tue Mar 06 11:15:37 UTC 2018
PRIMARY