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
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-XRQUGHPZSA-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
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 |
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0722 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
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 Date2011 |
|||
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 Date2011 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
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) Health Status: unhealthy Age Group: 43.5 years (range: 12.0–64.0 years) Sex: M+F 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 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) Health Status: unhealthy Age Group: 43.5 years (range: 12.0–64.0 years) Sex: M+F 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) Health Status: unhealthy Age Group: 43.5 years (range: 12.0–64.0 years) Sex: M+F 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) Health Status: unhealthy Age Group: 43.5 years (range: 12.0–64.0 years) Sex: M+F 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) Health Status: unhealthy Age Group: 43.5 years (range: 12.0–64.0 years) Sex: M+F 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 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 May |
|
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 |
|
Safety and tolerability of indacaterol in asthma: a randomized, placebo-controlled 28-day study. | 2007 Oct |
|
Gateways to clinical trials. | 2008 Jan-Feb |
|
Gateways to clinical trials. | 2009 Apr |
|
Lipid membrane interactions of indacaterol and salmeterol: do they influence their pharmacological properties? | 2009 Dec 8 |
|
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 |
|
Pharmacogenetic characterization of indacaterol, a novel beta 2-adrenoceptor agonist. | 2009 Sep |
|
Indacaterol maleate for the treatment of chronic obstructive pulmonary disease. | 2010 Aug |
|
Indacaterol once-daily is equally effective dosed in the evening or morning in COPD. | 2010 Dec |
|
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: a new once daily long-acting beta(2) adrenoceptor agonist. | 2010 Jun 15 |
|
Indacaterol for chronic obstructive pulmonary disease (COPD). | 2010 Mar |
|
Efficacy and safety of indacaterol 150 microg once-daily in COPD: a double-blind, randomised, 12-week study. | 2010 Mar 8 |
|
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 |
|
Long-acting beta-agonists in the management of chronic obstructive pulmonary disease: current and future agents. | 2010 Oct 29 |
|
Bronchodilator efficacy of single doses of indacaterol in Japanese patients with COPD: A randomised, double-blind, placebo-controlled trial. | 2010 Sep |
|
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
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Edited
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Record UNII |
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Record Version |
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