Indacaterol

Structural formula
General
Non-proprietary name	Indacaterol
other names	5 - [( R ) -2 - [(5,6-diethyl-2,3-dihydro-1 H -inden-2-yl) amino] -1-hydroxyethyl] -8-hydroxy-1,2-dihydroquinoline- 2-on ( IUPAC )
Molecular formula	C 24 H 28 N 2 O 3
External identifiers / databases
EC number	691-091-1
ECHA InfoCard	100.218.577
PubChem	6918554
DrugBank	DB05039
Wikidata	Q425654
Drug information
ATC code	R03 AC18
Drug class	β 2 sympathomimetics
properties
Molar mass	392.49 g · mol -1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-312-315-319-332-335
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Indacaterol is a drug from the group of β ₂ sympathomimetics . It is by means of a powder inhaler administered. It dilates the bronchi and has been approved for the treatment of chronic obstructive pulmonary diseases (COPD) in the European Union since November 30, 2009 and in Switzerland since October 21, 2010 .

pharmacology

Like all β ₂ -sympathomimetics, indacaterol dilates the bronchi by stimulating bronchial β ₂ -adrenoceptors and stimulates ciliary activity . It is characterized by an extremely long time of action (indacaterol is a so-called uLABA = English u ltra- l ong a cting b eta a gonist ). Therefore, in contrast to the long-acting β ₂ -sympathomimetics salmeterol and formoterol, it only has to be inhaled once a day. Compared to formoterol, indacaterol shows an improvement in some lung function parameters. However, it is still unclear whether this is clinically relevant.

Metabolism

Indacaterol is a substrate of UGT1A1 and is glucuronidated by it

Stereoisomerism

Indacaterol is the ( R ) form of 5- [2 - [(5,6-diethyl-2,3-dihydro-1 H -inden-2-yl) amino] -1-hydroxyethyl] -8-hydroxyquinoline-2 (1 H ) -one, a chiral molecule.

Trade names

Monopreparations for inhalation: Hirobriz (D), Onbrez (A, D, CH)
Combination preparation with glycopyrronium for inhalation: Ultibro (D)

Web links

Public Assessment Report (EPAR) of the European Medicines Agency (EMA) for: Indacaterol

Individual evidence

↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A label for 2 (1H) -quinolinones, 5 - [(1R) -2 - [(5,6-diethyl-2,3-dihydro-1H-inden-2-yl) amino is shown, which is derived from a self-classification by the distributor ] -1-hydroxyethyl] -8-hydroxy- in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 6, 2020.

↑ Beeh KM, Derom E, Kanniess F, Cameron R, Higgins M, van As A: Indacaterol, a novel inhaled beta2-agonist, provides sustained 24-h bronchodilation in asthma . In: Eur. Respir. J . 29, No. 5, May 2007, pp. 871-8. doi : 10.1183 / 09031936.00060006 . PMID 17251236 .

↑ Beier J, Beeh KM, Brookman L, Peachey G, Hmissi A, Pascoe S: Bronchodilator effects of indacaterol and formoterol in patients with COPD . In: Pulm Pharmacol Ther . 22, No. 6, December 2009, pp. 492-496. doi : 10.1016 / j.pupt.2009.05.001 . PMID 19465142 .

^ Medicines Commission of the German Medical Association, New Medicines: Onbrez Breezhaler (Indacaterol Maleate) (PDF; 442 kB), p. 109, March 22, 2010.

↑ Mark Kagan, Jeremy Dain, Lana Peng, Christine Reynolds: Metabolism and pharmacokinetics of indacaterol in humans . In: Drug Metabolism and Disposition: The Biological Fate of Chemicals . tape 40 , no. 9 , September 2012, p. 1712-1722 , doi : 10.1124 / dmd.112.046151 , PMID 22648561 .

↑ Battram C, Charlton SJ, Cuenoud B, Dowling MR, Fairhurst RA, Farr D, Fozard JR, Leighton-Davies JR, Lewis CA, McEvoy L, Turner RJ, Trifilieff A: 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-hour duration of action . In: J Pharmacol Exp Ther . 317, No. 2, May 2006, pp. 762-770. doi : 10.1124 / jpet.105.098251 . PMID 16434564 .

[1] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A label for 2 (1H) -quinolinones, 5 - [(1R) -2 - [(5,6-diethyl-2,3-dihydro-1H-inden-2-yl) amino is shown, which is derived from a self-classification by the distributor ] -1-hydroxyethyl] -8-hydroxy- in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 6, 2020.

[pmid17251236-2] Beeh KM, Derom E, Kanniess F, Cameron R, Higgins M, van As A: Indacaterol, a novel inhaled beta2-agonist, provides sustained 24-h bronchodilation in asthma . In: Eur. Respir. J . 29, No. 5, May 2007, pp. 871-8. doi : 10.1183 / 09031936.00060006 . PMID 17251236 .

[pmid19465142-3] Beier J, Beeh KM, Brookman L, Peachey G, Hmissi A, Pascoe S: Bronchodilator effects of indacaterol and formoterol in patients with COPD . In: Pulm Pharmacol Ther . 22, No. 6, December 2009, pp. 492-496. doi : 10.1016 / j.pupt.2009.05.001 . PMID 19465142 .

[4] Medicines Commission of the German Medical Association, New Medicines: Onbrez Breezhaler (Indacaterol Maleate) (PDF; 442 kB), p. 109, March 22, 2010.

[5] Mark Kagan, Jeremy Dain, Lana Peng, Christine Reynolds: Metabolism and pharmacokinetics of indacaterol in humans . In: Drug Metabolism and Disposition: The Biological Fate of Chemicals . tape 40 , no. 9 , September 2012, p. 1712-1722 , doi : 10.1124 / dmd.112.046151 , PMID 22648561 .

[pmid16434564-6] Battram C, Charlton SJ, Cuenoud B, Dowling MR, Fairhurst RA, Farr D, Fozard JR, Leighton-Davies JR, Lewis CA, McEvoy L, Turner RJ, Trifilieff A: 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-hour duration of action . In: J Pharmacol Exp Ther . 317, No. 2, May 2006, pp. 762-770. doi : 10.1124 / jpet.105.098251 . PMID 16434564 .