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
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
Molecular Formula | C24H28N2O3 |
Molecular Weight | 392.4907 |
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.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16022567
Curator's Comment: # Novartis
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20402514 |
76.0 nM [Ki] | ||
Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20655218 |
91.4 nM [Ki] | ||
Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20402514 |
76.0 nM [Ki] | ||
Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20655218 |
91.4 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ARCAPTA NEOHALER Approved UseUTIBRONTM 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 Date1.30947835E12 |
|||
Primary | ARCAPTA Approved UseINDICATIONS 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 Date1.29427204E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24705947/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24705947/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24705947/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24705947/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24705947/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24705947/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24705947/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24705947/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
116 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24705947/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24705947/ |
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
Dose | Population | Adverse 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) Sources: Wheezing (serious, 1 patient) Asthma (moderate, 1 patient) Cough (moderate, 1 patient) |
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... Other AEs: Adverse event (grade 5) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022383Orig1s000PharmR.pdf#page=46 Page: 46.0 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Gateways to clinical trials. | 2006 May |
|
Indacaterol Novartis/skyePharma. | 2006 May |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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: in chronic obstructive pulmonary disease. | 2010 Dec 3 |
|
Novel bronchodilators in asthma. | 2010 Jan |
|
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 |
|
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 |
|
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 |
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 Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16022567
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
Edited
Fri Dec 16 21:58:59 UTC 2022
by
admin
on
Fri Dec 16 21:58:59 UTC 2022
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Record UNII |
8OR09251MQ
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Record Status |
Validated (UNII)
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WHO-VATC |
QR03AC18
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NDF-RT |
N0000175779
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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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R03AC18
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R03AL04
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WHO-VATC |
QR03AL04
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE |
In vitro investigations indicated that indacaterol is a low affinity substrate for the efflux pump P-gp.
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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BINDER->LIGAND |
BINDING
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EXCRETED UNCHANGED |
URINE
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EXCRETED UNCHANGED |
FECAL
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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INTRAVENOUS INFUSION |
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Tmax | PHARMACOKINETIC |
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SINGLE OR REPEATED INHALED DOSES |
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