Indacaterol

Common Name

Indacaterol Description

Indacaterol is a novel, litra-long-acting, (2)-adrenoceptor agonist developed for Novartis for the once-daily treatment of asthma and chronic obstructive plimonary disease. It was approved by the European Medicines Agency (EMA) under the trade name Onbrez on November 30, 2009, and by the United States Food and Drug Administration (FDA), under the trade name Arcapta Neohaler, on Jliy 1, 2011. Indacaterol is provided as a pure R-enantiomer, typically as the salt indacaterol maleate. Structure

Synonyms

Value Source 5-(2-(5,6-Diethylindan-2-ylamino)-1-hydroxyethyl)-8-hydroxy-1H-quinolin-2-oneChEBI QAB 149ChEBI QAB-149ChEBI QAB149ChEBI Arcapta neohalerMeSH OnbrezMeSH

Chemical Formlia

C₂₄H₂₈N₂O₃ Average Molecliar Weight

392.4907 Monoisotopic Molecliar Weight

392.209992772 IUPAC Name

5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-1,2-dihydroquinolin-2-one Traditional Name

indacaterol CAS Registry Number

312753-06-3 SMILES

InChI Identifier

InChI Key

QZZUEBNBZAPZLX-QFIPXVFZSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as hydroxyquinolones. These are compounds containing a quinoline moiety bearing a hydroxyl group and a ketone. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. Kingdom

Organic compounds Super Class

Organoheterocyclic compounds Class

Quinolines and derivatives Sub Class

Quinolones and derivatives Direct Parent

Hydroxyquinolones Alternative Parents

8-hydroxyquinolines

Hydroxyquinolines

Hydroquinolones

Hydroquinolines

Indanes

1-hydroxy-2-unsubstituted benzenoids

Pyridinones

Aralkylamines

Heteroaromatic compounds

1,2-aminoalcohols

Secondary alcohols

Lactams

Azacyclic compounds

Dialkylamines

Aromatic alcohols

Organic oxides

Organopnictogen compounds

Hydrocarbon derivatives

Substituents

Hydroxyquinolone

Dihydroquinolone

Hydroxyquinoline

8-hydroxyquinoline

Dihydroquinoline

Indane

1-hydroxy-2-unsubstituted benzenoid

Pyridinone

Aralkylamine

Benzenoid

Pyridine

Heteroaromatic compound

1,2-aminoalcohol

Lactam

Secondary alcohol

Azacycle

Secondary aliphatic amine

Secondary amine

Aromatic alcohol

Organooxygen compound

Organonitrogen compound

Organic oxide

Organopnictogen compound

Organic oxygen compound

Amine

Organic nitrogen compound

Alcohol

Hydrocarbon derivative

Aromatic heteropolycyclic compound

Molecliar Framework

Aromatic heteropolycyclic compounds External Descriptors

secondary alcohol (CHEBI:68575 )

secondary amino compound (CHEBI:68575 )

indanes (CHEBI:68575 )

quinolone (CHEBI:68575 )

monohydroxyquinoline (CHEBI:68575 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Adrenergic beta-Agonists

Anti-Asthmatic Agents

Bronchodilator Agents

Application

Pharmaceutical

Cellliar locations

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting Point195 °C (decomposition)Not Available Boiling PointNot AvailableNot Available Water Solubility7.98e-03 g/LNot Available LogPNot AvailableNot Available

Predicted Properties

Property Value Source Water Solubility0.008 mg/mLALOGPS logP3.31ALOGPS logP3.26ChemAxon logS-4.7ALOGPS pKa (Strongest Acidic)8.51ChemAxon pKa (Strongest Basic)9.71ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area81.59 ŲChemAxon Rotatable Bond Count6ChemAxon Refractivity118.1 m³·mol^-1ChemAxon Polarizability44.96 ųChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB05039

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB05039

21059682

details

Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB05039 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

5293751 KEGG Compound ID

Not Available BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Indacaterol NuGOwiki Link

HMDB15608 Metagene Link

HMDB15608 METLIN ID

Not Available PubChem Compound

6918554 PDB ID

Not Available ChEBI ID

725589

Product: Naftifine (hydrochloride)

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References

1. Naline E, Trifilieff A, Fairhurst RA, Advenier C, Molimard M: Effect of indacaterol, a novel long-acting beta2-agonist, on isolated human bronchi. Eur Respir J. 2007 Mar;29(3):575-81. Epub 2006 Nov 29. [PubMed:17135231 ]
2. Kagan M, Dain J, Peng L, Reynolds C: Metabolism and pharmacokinetics of indacaterol in humans. Drug Metab Dispos. 2012 Sep;40(9):1712-22. doi: 10.1124/dmd.112.046151. Epub 2012 May 30. [PubMed:22648561 ]
3. Reid DJ, Pham NT: Emerging Therapeutic Options for the Management of COPD. Clin Med Insights Circ Respir Pulm Med. 2013 Apr 9;7:7-15. doi: 10.4137/CCRPM.S8140. Print 2013. [PubMed:23641160 ]
4. Australian Public Assessment Report [Link]

Enzymes

General function:

Involved in transferase activity, transferring hexosyl groups

Specific function:

UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.

Gene Name:

UGT1A1

Uniprot ID:

P22309

Molecular weight:

59590.91

General function:

Involved in monooxygenase activity

Specific function:

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.

Gene Name:

CYP3A4

Uniprot ID:

P08684

Molecular weight:

57255.585

General function:

Involved in G-protein coupled receptor protein signaling pathway

Specific function:

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine

Gene Name:

ADRB2

Uniprot ID:

P07550

Molecular weight:

46458.3

References

1. Cazzola M, Matera MG, Lotvall J: Ultra long-acting beta 2-agonists in development for asthma and chronic obstructive pulmonary disease. Expert Opin Investig Drugs. 2005 Jul;14(7):775-83. [PubMed:16022567 ]

PMID: 14599363

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Reverse transcriptase

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