Indacaterol maleate | CAS#753498-25-8 | 312753-06-3 | g beta-adrenoceptor agonist

MedKoo Cat#: 319521 | Name: Indacaterol maleate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Indacaterol is an ultra-long-acting beta-adrenoceptor agonist developed by Novartis. It was approved in 2009. 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.

Chemical Structure

Indacaterol maleate

CAS#753498-25-8 (malate)

Theoretical Analysis

MedKoo Cat#: 319521

Name: Indacaterol maleate

CAS#: 753498-25-8 (malate)

Chemical Formula: C28H32N2O7

Exact Mass: 0.0000

Molecular Weight: 508.57

Elemental Analysis: C, 66.13; H, 6.34; N, 5.51; O, 22.02

Price and Availability

Size	Price	Availability
100mg	USD 150.00	2 Weeks
200mg	USD 250.00	2 Weeks
500mg	USD 550.00	2 Weeks
1g	USD 950.00	2 Weeks
2g	USD 1,650.00	2 Weeks
5g	USD 3,650.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

753498-25-8 (malate) 312753-06-3 (free base)

Synonym

QAB-149; QAB 149; QAB149; Indacaterol maleate; trade name Onbrez Breezhale; arcapta neohaler; Onbrez.

IUPAC/Chemical Name

(R)-5-(2-((5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino)-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one maleate

InChi Key

IREJFXIHXRZFER-PCBAQXHCSA-N

InChi Code

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

SMILES Code

CCC1=C(C=C2CC(CC2=C1)NC[C@@H](C3=C4C=CC(=O)NC4=C(C=C3)O)O)CC.C(=C\C(=O)O)\C(=O)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Indacaterol maleate (QAB149) is an orally active ultra-long-acting β2 adrenergic receptor (ADRB2) agonist. Indacaterol maleate inhibits NF-κB activity in a β-arrestin2-dependent manner, preventing further lung damage and improving lung function in COPD (chronic obstructive pulmonary disorder). Indacaterol maleate can also be used in cardiovascular disease research.

In vitro activity:

As shown in Fig. 2A, TNF-α induced the phosphorylation of IκBα and IKKα/β (the upstream activators of NF-κB), but indacaterol pretreatments (both 5 and 10 μM) under the same conditions suppressed their phosphorylation. Moreover, consistent with this result, TNF-α-induced NF-κB nuclear translocation was also largely inhibited by pretreatments with 5 and 10 μM indacaterol (Fig. 2B). Therefore, these results suggest that indacaterol may inhibit NF-κB-dependent target gene expression by reducing the activity of NF-κB upstream activators. Reference: Mol Cells. 2014 Aug;37(8):585-91. https://pubmed.ncbi.nlm.nih.gov/25134539/

In vivo activity:

Treatment with either metoprolol or indacaterol alone significantly reduced the infarct size (8.50 ± 0.87% and 12.50 ± 1.44%, respectively; P < 0.001) with respect to untreated animals. Metoprolol or indacaterol alone or in combination significantly reduced cardiac GRK2 expression after 15 weeks in the failing rat hearts (Figure 2D, E). Reference: Br J Pharmacol. 2015 Jul;172(14):3627-37. https://pubmed.ncbi.nlm.nih.gov/25825265/

	Solvent	mg/mL	mM
Solubility
	DMSO	101.0	198.60

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 508.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Lee SU, Ahn KS, Sung MH, Park JW, Ryu HW, Lee HJ, Hong ST, Oh SR. Indacaterol inhibits tumor cell invasiveness and MMP-9 expression by suppressing IKK/NF-κB activation. Mol Cells. 2014 Aug;37(8):585-91. doi: 10.14348/molcells.2014.0076. Epub 2014 Aug 18. PMID: 25134539; PMCID: PMC4145369. 2. Scola AM, Loxham M, Charlton SJ, Peachell PT. The long-acting beta-adrenoceptor agonist, indacaterol, inhibits IgE-dependent responses of human lung mast cells. Br J Pharmacol. 2009 Sep;158(1):267-76. doi: 10.1111/j.1476-5381.2009.00178.x. Epub 2009 Apr 9. PMID: 19371332; PMCID: PMC2795262. 3. Rinaldi B, Donniacuo M, Sodano L, Gritti G, Martuscelli E, Orlandi A, Rafaniello C, Rossi F, Calzetta L, Capuano A, Matera MG. Effects of chronic treatment with the new ultra-long-acting β2 -adrenoceptor agonist indacaterol alone or in combination with the β1 -adrenoceptor blocker metoprolol on cardiac remodelling. Br J Pharmacol. 2015 Jul;172(14):3627-37. doi: 10.1111/bph.13148. Epub 2015 May 12. PMID: 25825265; PMCID: PMC4507164.

In vitro protocol:

In vivo protocol:

1. Rinaldi B, Donniacuo M, Sodano L, Gritti G, Martuscelli E, Orlandi A, Rafaniello C, Rossi F, Calzetta L, Capuano A, Matera MG. Effects of chronic treatment with the new ultra-long-acting β2 -adrenoceptor agonist indacaterol alone or in combination with the β1 -adrenoceptor blocker metoprolol on cardiac remodelling. Br J Pharmacol. 2015 Jul;172(14):3627-37. doi: 10.1111/bph.13148. Epub 2015 May 12. PMID: 25825265; PMCID: PMC4507164.

1: Rossi A, Zanardi E, Poletti V, Cazzola M. Clinical role of dual bronchodilation with an indacaterol-glycopyrronium combination in the management of COPD: its impact on patient-related outcomes and quality of life. Int J Chron Obstruct Pulmon Dis. 2015 Jul 23;10:1383-92. doi: 10.2147/COPD.S55488. eCollection 2015. Review. PubMed PMID: 26229457; PubMed Central PMCID: PMC4516211. 2: Horita N, Kaneko T. Role of combined indacaterol and glycopyrronium bromide (QVA149) for the treatment of COPD in Japan. Int J Chron Obstruct Pulmon Dis. 2015 Apr 21;10:813-22. doi: 10.2147/COPD.S56067. eCollection 2015. Review. PubMed PMID: 25960646; PubMed Central PMCID: PMC4410821. 3: Matera MG, Rogliani P, Cazzola M. QVA149 (indacaterol/glycopyrronium) for the treatment of chronic obstructive pulmonary disease. Expert Opin Pharmacother. 2015 May;16(7):1079-90. doi: 10.1517/14656566.2015.1032247. Epub 2015 Apr 5. Review. PubMed PMID: 25843089. 4: Pelaia G, Maselli R, Gallelli L. Pharmacologic rationale, efficacy and safety of the fixed-dose co-formulation of indacaterol and glycopyrronium. Multidiscip Respir Med. 2014 Dec 8;9(1):64. doi: 10.1186/2049-6958-9-64. eCollection 2014. Review. PubMed PMID: 25699181; PubMed Central PMCID: PMC4333835. 5: Ridolo E, Montagni M, Riario-Sforza GG, Baroni M, Incorvaia C. Combination therapy with indacaterol and glycopyrronium bromide in the management of COPD: an update on the evidence for efficacy and safety. Ther Adv Respir Dis. 2015 Apr;9(2):49-55. doi: 10.1177/1753465815572065. Epub 2015 Feb 17. Review. PubMed PMID: 25691493. 6: Prakash A, Babu KS, Morjaria JB. Profile of inhaled glycopyrronium bromide as monotherapy and in fixed-dose combination with indacaterol maleate for the treatment of COPD. Int J Chron Obstruct Pulmon Dis. 2015 Jan 7;10:111-23. doi: 10.2147/COPD.S67758. eCollection 2015. Review. PubMed PMID: 25609944; PubMed Central PMCID: PMC4293295. 7: Pelaia G, Maselli R, Matera MG. Treatment of chronic obstructive pulmonary disease by dual bronchodilation with coformulation of indacaterol/glycopyrronium. Pharmacology. 2014;94(5-6):249-58. doi: 10.1159/000368986. Epub 2014 Nov 28. Review. PubMed PMID: 25471458. 8: Murphy L, Rennard S, Donohue J, Molimard M, Dahl R, Beeh KM, Dederichs J, Fülle HJ, Higgins M, Young D. Turning a molecule into a medicine: the development of indacaterol as a novel once-daily bronchodilator treatment for patients with COPD. Drugs. 2014 Sep;74(14):1635-57. doi: 10.1007/s40265-014-0284-7. Review. PubMed PMID: 25212789. 9: Roskell NS, Anzueto A, Hamilton A, Disse B, Becker K. Once-daily long-acting beta-agonists for chronic obstructive pulmonary disease: an indirect comparison of olodaterol and indacaterol. Int J Chron Obstruct Pulmon Dis. 2014 Jul 31;9:813-24. doi: 10.2147/COPD.S59673. eCollection 2014. Review. PubMed PMID: 25114521; PubMed Central PMCID: PMC4124050. 10: Ulrik CS. Clinical benefit of fixed-dose dual bronchodilation with glycopyrronium and indacaterol once daily in patients with chronic obstructive pulmonary disease: a systematic review. Int J Chron Obstruct Pulmon Dis. 2014 Apr 1;9:331-8. doi: 10.2147/COPD.S60362. eCollection 2014. Review. PubMed PMID: 24729699; PubMed Central PMCID: PMC3979690. 11: Frampton JE. QVA149 (indacaterol/glycopyrronium fixed-dose combination): a review of its use in patients with chronic obstructive pulmonary disease. Drugs. 2014 Mar;74(4):465-88. doi: 10.1007/s40265-014-0194-8. Review. PubMed PMID: 24604791. 12: Rodrigo GJ, Plaza V. Efficacy and safety of a fixed-dose combination of indacaterol and Glycopyrronium for the treatment of COPD: a systematic review. Chest. 2014 Aug;146(2):309-17. doi: 10.1378/chest.13-2807. Review. PubMed PMID: 24556877. 13: Seth HD, Sultan S, Gotfried MH. Role of indacaterol, a once-daily bronchodilator, in chronic obstructive pulmonary disease. J Thorac Dis. 2013 Dec;5(6):806-14. doi: 10.3978/j.issn.2072-1439.2013.10.11. Review. PubMed PMID: 24409359; PubMed Central PMCID: PMC3886694. 14: Steiropoulos P, Archontogeorgis K, Nena E, Bouros D. New developments in the management of COPD: clinical utility of indacaterol 75 μg. Int J Chron Obstruct Pulmon Dis. 2014;9:1-7. doi: 10.2147/COPD.S24940. Epub 2013 Dec 6. Review. PubMed PMID: 24353414; PubMed Central PMCID: PMC3862584. 15: Cazzola M, Calzetta L, Page CP, Matera MG. Use of indacaterol for the treatment of COPD: a pharmacokinetic evaluation. Expert Opin Drug Metab Toxicol. 2014 Jan;10(1):129-37. doi: 10.1517/17425255.2014.865723. Epub 2013 Dec 3. Review. PubMed PMID: 24295085. 16: Ridolo E, Montagni M, Olivieri E, Riario-Sforza GG, Incorvaia C. Role of indacaterol and the newer very long-acting β2-agonists in patients with stable COPD: a review. Int J Chron Obstruct Pulmon Dis. 2013;8:425-32. doi: 10.2147/COPD.S49179. Epub 2013 Sep 18. Review. PubMed PMID: 24082783; PubMed Central PMCID: PMC3785397. 17: Chung VC, Ma PH, Hui DS, Tam WW, Tang JL. Indacaterol for chronic obstructive pulmonary disease: systematic review and meta-analysis. PLoS One. 2013 Aug 14;8(8):e70784. doi: 10.1371/journal.pone.0070784. eCollection 2013. Review. PubMed PMID: 23967106; PubMed Central PMCID: PMC3743831. 18: Rossi A, Polese G. Indacaterol: a comprehensive review. Int J Chron Obstruct Pulmon Dis. 2013;8:353-63. doi: 10.2147/COPD.S21625. Epub 2013 Jul 25. Review. PubMed PMID: 23922496; PubMed Central PMCID: PMC3728154. 19: Schachter EN. Indacaterol/glycopyrronium bromide fixed-dose combination for the treatment of COPD. Drugs Today (Barc). 2013 Jul;49(7):437-46. doi: 10.1358/dot.2013.49.7.1980496. Review. PubMed PMID: 23914352. 20: Han J, Dai L, Zhong N. Indacaterol on dyspnea in chronic obstructive pulmonary disease: a systematic review and meta-analysis of randomized placebo-controlled trials. BMC Pulm Med. 2013 Apr 25;13:26. doi: 10.1186/1471-2466-13-26. Review. PubMed PMID: 23617268; PubMed Central PMCID: PMC3651265.