Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H28N2O3.C4H4O4 |
Molecular Weight | 508.564 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCc1cc2CC(Cc2cc1CC)NC[C@@]([H])(c3ccc(c4c3ccc(n4)O)O)O.C(\[H])(=C(\[H])/C(=O)O)/C(=O)O
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
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 |
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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 |
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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 |
|
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 |
|
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 |
|
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 |
|
Bronchodilator efficacy of indacaterol, a novel once-daily beta2-agonist, in patients with persistent asthma. | 2008 Jul |
|
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. | 2009 Apr |
|
Bronchodilator effects of indacaterol and formoterol in patients with COPD. | 2009 Dec |
|
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 |
|
Indacaterol, a novel inhaled, once-daily, long-acting beta2-agonist for the treatment of obstructive airways diseases. | 2009 Jul |
|
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 |
|
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 |
|
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 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 |
|
Efficacy of a new once-daily long-acting inhaled beta2-agonist indacaterol versus twice-daily formoterol in COPD. | 2010 Jun |
|
Integrating indacaterol dose selection in a clinical study in COPD using an adaptive seamless design. | 2010 Jun |
|
Indacaterol for chronic obstructive pulmonary disease (COPD). | 2010 Mar |
|
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 |
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)
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Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
OSLIF BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by
admin on Sat Jun 26 10:56:03 UTC 2021 , Edited by admin on Sat Jun 26 10:56:03 UTC 2021
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EMA ASSESSMENT REPORTS |
HIROBRIZ BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by
admin on Sat Jun 26 10:56:03 UTC 2021 , Edited by admin on Sat Jun 26 10:56:03 UTC 2021
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NCI_THESAURUS |
C48149
Created by
admin on Sat Jun 26 10:56:03 UTC 2021 , Edited by admin on Sat Jun 26 10:56:03 UTC 2021
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EMA ASSESSMENT REPORTS |
ULUNAR BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by
admin on Sat Jun 26 10:56:03 UTC 2021 , Edited by admin on Sat Jun 26 10:56:03 UTC 2021
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EMA ASSESSMENT REPORTS |
ONBREZ BREEZHALER (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by
admin on Sat Jun 26 10:56:03 UTC 2021 , Edited by admin on Sat Jun 26 10:56:03 UTC 2021
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1114325
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2JEC1ITX7R
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9827599
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753498-25-8
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DBSALT000101
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435273-74-8
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NON-SPECIFIC STOICHIOMETRY | |||
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M6240
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CHEMBL1095777
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SUB30300
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C81640
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD