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Indacaterol
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Systematic (IUPAC) name |
(R)-5-[2-[(5,6-Diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxyquinolin-2(1H)-one |
Clinical data |
Trade names |
Onbrez, Arcapta |
AHFS/Drugs.com |
International Drug Names |
Licence data |
EMA:Link, US FDA:link |
Pregnancy cat. |
C (US) |
Legal status |
POM (UK) ℞-only (US) |
Routes |
Inhalation |
Identifiers |
CAS number |
312753-06-3 Y |
ATC code |
R03AC18 |
PubChem |
CID 6433117 |
ChemSpider |
5293751 Y |
UNII |
8OR09251MQ Y |
KEGG |
D09318 Y |
ChEBI |
CHEBI:68575 Y |
ChEMBL |
CHEMBL1095777 Y |
Chemical data |
Formula |
C24H28N2O3 |
Mol. mass |
392.490 g/mol |
SMILES
- O=C4/C=C\c1c(c(O)ccc1[C@@H](O)CNC3Cc2cc(c(cc2C3)CC)CC)N4
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InChI
-
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 Y
Key:QZZUEBNBZAPZLX-QFIPXVFZSA-N Y
|
Y (what is this?) (verify)
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Indacaterol (INN) is an ultra-long-acting beta-adrenoceptor agonist[1] developed by Novartis. It was approved by the European Medicines Agency (EMA) under the trade name Onbrez on November 30, 2009,[2] and by the United States Food and Drug Administration (FDA), under the trade name Arcapta Neohaler, on July 1, 2011.[3] It needs to be taken only once a day,[4] unlike the currently available 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.
Clinical trials[edit]
A Phase III trial published in March 2010 examined the efficacy and safety of indacaterol in COPD patients.[5] This study, conducted in the U.S., New Zealand, and Belgium, compared indacaterol dry-powder inhaler to placebo in 416 COPD patients, mostly moderate to severe (mean FEV1 of 1.5 L). Indacaterol produced statistically improved FEV1 (both trough and AUC) and decreased use of rescue medication compared to placebo, but with safety and tolerability similar to those of placebo.
A year-long, placebo-controlled trial published in July 2010 suggests indacaterol may be significantly more effective than twice-daily formoterol in improving FEV1. There were some reductions in the need for rescue medication, but these were not significantly different; nor was there any difference in the rate of exacerbation between the 2 active treatments.[6]
A study published in October, 2011 in the European Respiratory Journal compared indacaterol with tiotropium over the study period of 12 weeks. The study found no statistical difference between the effects of the two drugs on FEV1. Indacaterol yielded greater improvements in transition dyspnoea index (TDI) total score and St. George’s Respiratory Questionnaire (SGRQ) total score.[7]
References[edit]
- ^ Cazzola M, Matera MG, Lötvall J (July 2005). "Ultra long-acting beta 2-agonists in development for asthma and chronic obstructive pulmonary disease". Expert Opin Investig Drugs 14 (7): 775–83. doi:10.1517/13543784.14.7.775. PMID 16022567.
- ^ European Public Assessment Report for Onbrez Breezhaler
- ^ "FDA approves Arcapta Neohaler to treat chronic obstructive pulmonary disease" (Press release). U.S. Food and Drug Administration. 2011-07-01. Retrieved 2011-07-02. [1]
- ^ Beeh KM, Derom E, Kanniess F, Cameron R, Higgins M, van As A (May 2007). "Indacaterol, a novel inhaled beta2-agonist, provides sustained 24-h bronchodilation in asthma". Eur. Respir. J. 29 (5): 871–8. doi:10.1183/09031936.00060006. PMID 17251236.
- ^ Feldman, G; Siler, T; Prasad, N; Jack, D; Piggott, S; Owen, R; Higgins, M; Kramer, B et al. (2010). "Efficacy and safety of indacaterol 150 mcg once-daily in COPD: a double-blind, randomised, 12-week study.". BMC pulmonary medicine 10: 11. doi:10.1186/1471-2466-10-11. PMC 2848004. PMID 20211002.
- ^ Dahl R, Chung KF, Buhl R, et al. (June 2010). "Efficacy of a new once-daily long-acting inhaled beta2-agonist indacaterol versus twice-daily formoterol in COPD". Thorax 65 (6): 473–9. doi:10.1136/thx.2009.125435. PMID 20522841.
- ^ R. Buhl, L.J. Dunn, C. Disdier, et al. (October 2011). "Blinded 12-week comparison of once-daily indacaterol and tiotropium in COPD". European Respiratory Journal 38 (4): 797–803. PMID 21622587.
Adrenergics
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Receptor ligands
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α1
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- Agonists: 5-FNE
- 6-FNE
- Amidephrine
- Anisodamine
- Anisodine
- Cirazoline
- Dipivefrine
- Dopamine
- Ephedrine
- Epinephrine
- Etilefrine
- Ethylnorepinephrine
- Indanidine
- Levonordefrin
- Metaraminol
- Methoxamine
- Methyldopa
- Midodrine
- Naphazoline
- Norepinephrine
- Octopamine
- Oxymetazoline
- Phenylephrine
- Phenylpropanolamine
- Pseudoephedrine
- Synephrine
- Tetrahydrozoline
Antagonists: Abanoquil
- Adimolol
- Ajmalicine
- Alfuzosin
- Amosulalol
- Arotinolol
- Atiprosin
- Benoxathian
- Buflomedil
- Bunazosin
- Carvedilol
- CI-926
- Corynanthine
- Dapiprazole
- DL-017
- Domesticine
- Doxazosin
- Eugenodilol
- Fenspiride
- GYKI-12,743
- GYKI-16,084
- Hydroxyzine
- Indoramin
- Ketanserin
- L-765,314
- Labetalol
- Mephendioxan
- Metazosin
- Monatepil
- Moxisylyte
- Naftopidil
- Nantenine
- Neldazosin
- Nicergoline
- Niguldipine
- Pelanserin
- Phendioxan
- Phenoxybenzamine
- Phentolamine
- Piperoxan
- Prazosin
- Quinazosin
- Ritanserin
- RS-97,078
- SGB-1,534
- Silodosin
- SL-89.0591
- Spiperone
- Talipexole
- Tamsulosin
- Terazosin
- Tibalosin
- Tiodazosin
- Tipentosin
- Tolazoline
- Trimazosin
- Upidosin
- Urapidil
- Zolertine
- Note that many TCAs, TeCAs, antipsychotics, ergolines, and some piperazines like buspirone and trazodone all antagonize α1-adrenergic receptors as well, which contributes to their side effects such as orthostatic hypotension.
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α2
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- Agonists: (R)-3-Nitrobiphenyline
- 4-NEMD
- 6-FNE
- Amitraz
- Apraclonidine
- Brimonidine
- Cannabivarin
- Clonidine
- Detomidine
- Dexmedetomidine
- Dihydroergotamine
- Dipivefrine
- Dopamine
- Ephedrine
- Ergotamine
- Epinephrine
- Esproquin
- Etilefrine
- Ethylnorepinephrine
- Guanabenz
- Guanfacine
- Guanoxabenz
- Levonordefrin
- Lofexidine
- Medetomidine
- Methyldopa
- Mivazerol
- Naphazoline
- Norepinephrine
- Oxymetazoline
- Phenylpropanolamine
- Piperoxan
- Pseudoephedrine
- Rilmenidine
- Romifidine
- Talipexole
- Tetrahydrozoline
- Tizanidine
- Tolonidine
- Urapidil
- Xylazine
- Xylometazoline
Antagonists: 1-PP
- Adimolol
- Aptazapine
- Atipamezole
- BRL-44408
- Buflomedil
- Cirazoline
- Efaroxan
- Esmirtazapine
- Fenmetozole
- Fluparoxan
- GYKI-12,743
- GYKI-16,084
- Idazoxan
- Mianserin
- Mirtazapine
- MK-912
- NAN-190
- Olanzapine
- Phentolamine
- Phenoxybenzamine
- Piperoxan
- Piribedil
- Rauwolscine
- Rotigotine
- SB-269,970
- Setiptiline
- Spiroxatrine
- Sunepitron
- Tolazoline
- Yohimbine
* Note that many atypical antipsychotics and azapirones like buspirone (via metabolite 1-PP) antagonize α2-adrenergic receptors as well.
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β
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Reuptake inhibitors
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NET
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- Selective norepinephrine reuptake inhibitors: Amedalin
- Atomoxetine (Tomoxetine)
- Ciclazindol
- Daledalin
- Edivoxetine
- Esreboxetine
- Lortalamine
- Mazindol
- Nisoxetine
- Reboxetine
- Talopram
- Talsupram
- Tandamine
- Viloxazine; Norepinephrine-dopamine reuptake inhibitors: Amineptine
- Bupropion (Amfebutamone)
- Fencamine
- Fencamfamine
- Lefetamine
- Levophacetoperane
- LR-5182
- Manifaxine
- Methylphenidate
- Nomifensine
- O-2172
- Radafaxine; Serotonin-norepinephrine reuptake inhibitors: Bicifadine
- Desvenlafaxine
- Duloxetine
- Eclanamine
- Levomilnacipran
- Milnacipran
- Sibutramine
- Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors: Brasofensine
- Diclofensine
- DOV-102,677
- DOV-21,947
- DOV-216,303
- JNJ-7925476
- JZ-IV-10
- Methylnaphthidate
- Naphyrone
- NS-2359
- PRC200-SS
- SEP-225,289
- SEP-227,162
- Tesofensine; Tricyclic antidepressants: Amitriptyline
- Butriptyline
- Cianopramine
- Clomipramine
- Desipramine
- Dosulepin
- Doxepin
- Imipramine
- Lofepramine
- melitracen
- Nortriptyline
- Protriptyline
- Trimipramine; Tetracyclic antidepressants: Amoxapine
- Maprotiline
- Mianserin
- Oxaprotiline
- Setiptiline; Others: Cocaine
- CP-39,332
- Ethanol
- EXP-561
- Fezolamine
- Ginkgo biloba
- Indeloxazine
- Nefazodone
- Nefopam
- Pridefrine
- Tapentadol
- Tedatioxetine
- Teniloxazine
- Tofenacin
- Tramadol
- Ziprasidone
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VMAT
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- Ibogaine
- Reserpine
- Tetrabenazine
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Enzyme inhibitors
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Anabolism
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PAH
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TH
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- 3-Iodotyrosine
- Aquayamycin
- Bulbocapnine
- Metirosine
- Oudenone
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AAAD
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- Benserazide
- Carbidopa
- DFMD
- Genistein
- Methyldopa
|
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DBH
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- Bupicomide
- Disulfiram
- Dopastin
- Fusaric acid
- Nepicastat
- Phenopicolinic acid
- Tropolone
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PNMT
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- CGS-19281A
- SKF-64139
- SKF-7698
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Catabolism
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MAO
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- Nonselective: Benmoxin
- Caroxazone
- Echinopsidine
- Furazolidone
- Hydralazine
- Indantadol
- Iproclozide
- Iproniazid
- Isocarboxazid
- Isoniazid
- Linezolid
- Mebanazine
- Metfendrazine
- Nialamide
- Octamoxin
- Paraxazone
- Phenelzine
- Pheniprazine
- Phenoxypropazine
- Pivalylbenzhydrazine
- Procarbazine
- Safrazine
- Tranylcypromine; MAO-A selective: Amiflamine
- Bazinaprine
- Befloxatone
- Befol
- Brofaromine
- Cimoxatone
- Clorgiline
- Esuprone
- Harmala alkaloids (Harmine,
- Harmaline
- Tetrahydroharmine
- Harman
- Norharman, etc)
- Methylene blue
- Metralindole
- Minaprine
- Moclobemide
- Pirlindole
- Sercloremine
- Tetrindole
- Toloxatone
- Tyrima; MAO-B selective:
- Ladostigil
- Lazabemide
- Milacemide
- Mofegiline
- Pargyline
- Rasagiline
- Safinamide
- Selegiline (also D-Deprenyl)
* Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.
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COMT
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- Entacapone
- Nitecapone
- Tolcapone
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Others
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Precursors
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- L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine
- L-DOPS (Droxidopa)
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Cofactors
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- Ferrous Iron (Fe2+)
- S-Adenosyl-L-Methionine
- Vitamin B3 (Niacin
- Nicotinamide → NADPH)
- Vitamin B6 (Pyridoxine
- Pyridoxamine
- Pyridoxal → Pyridoxal Phosphate)
- Vitamin B9 (Folic acid → Tetrahydrofolic acid)
- Vitamin C (Ascorbic acid)
- Zinc (Zn2+)
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Others
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- Activity enhancers: BPAP
- PPAP; Release blockers: Bethanidine
- Bretylium
- Guanadrel
- Guanazodine
- Guanclofine
- Guanethidine
- Guanoxan; Toxins: 6-OHDA
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List of adrenergic drugs
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Drugs for obstructive airway diseases: asthma/COPD (R03)
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Adrenergics, inhalants |
Short acting β2-agonists |
- Bitolterol
- Carbuterol
- Fenoterol
- Pirbuterol
- Procaterol
- Reproterol
- Rimiterol
- Salbutamol#/Levosalbutamol
- Terbutaline
- Tulobuterol
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Long acting β2-agonists (LABA) |
- Arformoterol
- Bambuterol
- Clenbuterol
- Formoterol
- Olodaterol
- Salmeterol
- Ultra LABA: Indacaterol
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other |
- Epinephrine#
- Hexoprenaline
- Isoprenaline (Isoproterenol)
- Orciprenaline (Metaproterenol)
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Glucocorticoids |
- Beclometasone#
- Betamethasone
- Budesonide
- Ciclesonide
- Flunisolide
- Fluticasone
- Mometasone
- Triamcinolone
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Anticholinergics/
muscarinic antagonist |
- Aclidinium bromide
- Glycopyrronium bromide
- Ipratropium bromide#
- Oxitropium bromide
- Tiotropium bromide
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Mast cell stabilizers |
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Xanthines |
- Doxofylline
- Enprofylline
- Theobromine
- Theophylline/Aminophylline/Choline theophyllinate
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Eicosanoid inhibition |
Leukotriene antagonists |
- Montelukast
- Pranlukast
- Zafirlukast
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Lipoxygenase inhibitor |
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Thromboxane receptor antagonists |
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Combination products |
- Budesonide/formoterol
- Fluticasone/salmeterol
- Ipratropium bromide/salbutamol
- Mometasone/formoterol
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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anat (n, x, l, c)/phys/devp
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noco (c, p)/cong/tumr, sysi/epon, injr
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proc, drug (R1/2/3/5/6/7)
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UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
English Journal
- Update on ultra-long-acting β agonists in chronic obstructive pulmonary disease.
- Zafar MA1, Droege C, Foertsch M, Panos RJ.
- Expert opinion on investigational drugs.Expert Opin Investig Drugs.2014 Dec;23(12):1687-701. doi: 10.1517/13543784.2014.942730. Epub 2014 Aug 19.
- INTRODUCTION: For the last two decades, long-acting β agonists (LABAs) have been a cornerstone in the management of chronic obstructive pulmonary disease (COPD). They relax airway smooth muscle and augment expiratory airflow, which reduces hyperinflation and improves dyspnea, functional capacity an
- PMID 25139313
- Indacaterol for the treatment of chronic obstructive pulmonary disease.
- Matera MG1, Rogliani P, Cazzola M.
- Expert opinion on pharmacotherapy.Expert Opin Pharmacother.2014 Nov 24:1-9. [Epub ahead of print]
- Introduction: The need for a rapid onset of action and a long duration of the broncholytic effect is the likely reason for the development of new long-acting β2-agonists (LABAs) that are fast acting and have true 24 h duration of action. Indacaterol is the archetype of once-daily LABAs and already
- PMID 25418284
- INSTEAD: a randomised switch trial of indacaterol versus salmeterol/fluticasone in moderate COPD.
- Rossi A1, van der Molen T2, Olmo RD3, Papi A4, Wehbe L5, Quinn M6, Lu C6, Young D7, Cameron R7, Bucchioni E8, Altman P6.
- The European respiratory journal.Eur Respir J.2014 Dec;44(6):1548-56. doi: 10.1183/09031936.00126814. Epub 2014 Oct 30.
- The Indacaterol: Switching Non-exacerbating Patients with Moderate COPD From Salmeterol/Fluticasone to Indacaterol (INSTEAD) study investigated the effect of switching patients at low risk of chronic obstructive pulmonary disease (COPD) exacerbations from salmeterol/fluticasone (SFC; inhaled cortico
- PMID 25359348
Japanese Journal
- 慢性閉塞性肺疾患に対するチオトロピウムとインダカテロールの併用療法からグリコピロニウム/インダカテロール配合剤への切り替えの検討 : 単施設での自己対照比較研究
- 臨床 新薬レビュー グリコピロニウム臭化物/インダカテロールマレイン酸塩 Glycopyrronium Bromide/Indacaterol Maleate ウルティブロ吸入用カプセル ノバルティス ファーマ
- COPDの吸入治療の第一選択は吸入抗コリン薬(LAMA)か吸入β刺激薬(LABA)か? (特集 COPD治療の新時代 : 21世紀の「社会的」生活習慣病) -- (COPD治療のコントラバシー)
Related Links
- Read more about the pharmacogenomics of indacaterol on PharmGKB. ... Disclaimer: The PharmGKB's clinical annotations reflect expert consensus based on clinical evidence and peer-reviewed literature available at the time ...
- PBS listing Restricted benefit Indacaterol (Onbrez) is PBS listed as a Restricted Benefit for treatment of chronic obstructive pulmonary disease. 1 May be prescribed by nurse practitioners Authorised nurse practitioners may prescribe ...
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