Indacaterol

Base Information

• Chemical Name: Indacaterol
• CAS No.: 312753-06-3
• Deprecated CAS: 870265-20-6
• Molecular Formula: C24H28N2O3
• Molecular Weight: 392.498
• European Community (EC) Number: 691-091-1
• UNII: 8OR09251MQ
• DSSTox Substance ID: DTXSID90185198
• Nikkaji Number: J2.407.733K
• Wikipedia: Indacaterol
• Wikidata: Q425654
• NCI Thesaurus Code: C81644
• Pharos Ligand ID: 4TS2LN8JSSNQ
• Metabolomics Workbench ID: 43648
• ChEMBL ID: CHEMBL1095777
• Mol file: 312753-06-3.mol

Synonyms:5-(2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl)-8-hydroxy-1H-quinolin-2-one;arcapta neohaler;indacaterol;Onbrez;QAB-149

Chemical Property of Indacaterol

Chemical Property:

• Vapor Pressure: 2.47E-18mmHg at 25°C
• Refractive Index: 1.659
• Boiling Point: 660.3 °C at 760 mmHg
• PKA: 8.68±0.20(Predicted)
• Flash Point: 353.1 °C
• PSA: 85.35000
• Density: 1.27 g/cm³
• LogP: 3.53980
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 392.20999276
• Heavy Atom Count: 29
• Complexity: 589

Purity/Quality:

99%min ^*data from raw suppliers

Indacaterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=C(C=C2CC(CC2=C1)NCC(C3=C4C=CC(=O)NC4=C(C=C3)O)O)CC
• Isomeric SMILES: CCC1=C(C=C2CC(CC2=C1)NC[C@@H](C3=C4C=CC(=O)NC4=C(C=C3)O)O)CC
• Recent ClinicalTrials: A Study to Evaluate the Efficacy and Safety of QMF149 (Indacaterol Acetate/Mometasone Furoate) Versus Budesonide in Children From 6 to Less Than 12 Years of Age With Asthma
• Recent EU Clinical Trials: An open-label, two-period, single-sequence, crossover study to compare the systemic exposure of a single inhaled dose of mometasone furoate (MF) when administered alone via the MF Twisthaler? (TH) to a single inhaled dose of QMF149 indacaterol acetate/MF fixed dose combination when administered via the Concept 1 (Breezhaler?) device in ≥ 6 to <12 year old asthma patients
• Recent NIPH Clinical Trials: A randomized prospective controlled trial of long-acting muscarinic antagonist and long-acting be-ta2 agonist fixed dose combinations in patients with chronic obstructive pulmonary disease: Effects on quality of life and pulmonary function and preference
• Description: Indacaterol is a new, ultra-long-acting, rapid onset β(2)-adrenoceptor agonist that was developed by Novartis. The drug is used in managing and controlling chronic obstructive pulmonary disease (COPD) and asthma. The European Medicines Agency (EMA) approved indacaterol as a drug in 2009 under the Onbrez trade name while in the United States the Food and Drug Administration approved it under the trade name Arcapta in 2011. The drug is manufactured as its maleate salt form. Also, indacaterol is a chiral molecule; however, only the pure R-enantiomer is distributed. Inhaled β2 adrenoceptor agonists are effective in the management of asthma and COPD, primarily through their bronchodilating properties. These drugs induce bronchodilation by causing direct relaxation of airway smooth muscle through activation of adenylate cyclase, which in turn increases intracellular cAMP levels. Indacaterol is the newest β2 agonist to reach the market. It is an ultra-long-acting agent with a duration of action suitable for once-a-day dosing. Indacaterol is supplied as an aerosol formulation of its maleate salt and is administered via a dry powder inhaler device. It is specifically approved for once-daily maintenance treatment of airflow obstruction in adult patients with COPD. In preclinical models, indacaterol is close to a full agonist at the human b2 adrenoceptor (Emax = 73 ± 1% of isoprenaline′s maximal effect, pEC50 = 8.06 ±0.02) while salmeterol displays only partial efficacy (38 ±1%). The functional selectivity profile of indacaterol over β1 human adrenoceptors is similar to that of formoterol, whereas its β3 adrenoceptor selectivity profile is similar to that of formoterol and salbutamol.
• Uses: Indacaterol is a β-adrenoreceptor agonists for treatment of asthma and bronchodilator treatment for patients with chronic obstructive pulmonary diseases.

Technology Process of Indacaterol

There total 33 articles about Indacaterol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.84%

indacaterol maleate (753498-25-8) → indacaterol (312753-06-3)

Guidance literature:

With lithium hydroxide monohydrate; In methanol; at 35 ℃; for 1h; Reagent/catalyst;

Reference yield: 97.0%

(R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one (435273-75-9) → indacaterol (312753-06-3)

Guidance literature:

(R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one; With 5%-palladium/activated carbon; hydrogen; In ethanol; at 20 ℃; for 2h;

With 5%-palladium/activated carbon; hydrogen; In ethanol; at 40 ℃; for 4h; under 757.576 Torr;

Reference yield: 86.2%

5-{(1R)-2-[(N-benzyl-5,6-diethyl-2,3-dihydro-1H-indan-2-yl)amino]-1-hydroxyethyl}-8-benzyloxy-1H-quinolin-2-one → indacaterol (312753-06-3)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; acetic acid; In methanol; at 20 ℃;

upstream raw materials:

(R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

8-(phenylmethoxy)-5-[(R)-2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-(1H)-quinolin-2-one tartrate

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one

Downstream raw materials:

indacaterol maleate

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one fumarate

Refernces

• 1、 -. "A maleic acid yin dutrow intermediate and its preparation and use". Paragraph 0081-0083. . Retrieved 2019/05/16.
• 2、 -. "A Process for Preparing Indacaterol and Salts Thereof". Paragraph 0062. . Retrieved 2018/08/20.