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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

PubMed

PubMed

TitleDatePubMed
Gateways to clinical trials.
2007 Jan-Feb
Gateways to clinical trials.
2008 Oct
Cardiovascular safety of QVA149, a combination of Indacaterol and NVA237, in COPD patients.
2010 Dec
Indacaterol: in chronic obstructive pulmonary disease.
2010 Dec 3
[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
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
Cost Effectiveness of the Long-Acting β2-Adrenergic Agonist (LABA)/Long-Acting Muscarinic Antagonist Dual Bronchodilator Indacaterol/Glycopyrronium Versus the LABA/Inhaled Corticosteroid Combination Salmeterol/Fluticasone in Patients with Chronic Obstructive Pulmonary Disease: Analyses Conducted for Canada, France, Italy, and Portugal.
2016 Oct
An update on LAMA/LABA combinations for COPD.
2017 Jan
Indacaterol and glycopyrronium versus indacaterol on body plethysmography measurements in COPD-a randomised controlled study.
2017 Jan 11
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)
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