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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

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

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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

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 Jan-Feb
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
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
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
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
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
Gateways to clinical trials.
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: in chronic obstructive pulmonary disease.
2010 Dec 3
Once-daily bronchodilators for chronic obstructive pulmonary disease: indacaterol versus tiotropium.
2010 Jul 15
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
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

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)
Substance Class Chemical
Created
by admin
on Mon Oct 21 23:49:38 UTC 2019
Edited
by admin
on Mon Oct 21 23:49:38 UTC 2019
Record UNII
2JEC1ITX7R
Record Status Validated (UNII)
Record Version
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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
QVA-149 COMPONENT INDACATEROL 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
ULTIBRO COMPONENT INDACATEROL MALEATE
Brand 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
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 Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
EMA ASSESSMENT REPORTS HIROBRIZ BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Mon Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
NCI_THESAURUS C48149
Created by admin on Mon Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
EMA ASSESSMENT REPORTS ULUNAR BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Mon Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
EMA ASSESSMENT REPORTS ONBREZ BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Mon Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
Code System Code Type Description
RXCUI
1114325
Created by admin on Mon Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
PRIMARY RxNorm
PUBCHEM
9827599
Created by admin on Mon Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
PRIMARY
CAS
753498-25-8
Created by admin on Mon Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
PRIMARY
CAS
435273-74-8
Created by admin on Mon Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
NON-SPECIFIC STOICHIOMETRY
MERCK INDEX
M6240
Created by admin on Mon Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL1095777
Created by admin on Mon Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
PRIMARY
EVMPD
SUB30300
Created by admin on Mon Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
PRIMARY
NCI_THESAURUS
C81640
Created by admin on Mon Oct 21 23:49:38 UTC 2019 , Edited by admin on Mon Oct 21 23:49:38 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY