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

• ChemBase ID: 171579
• Molecular Formular: C24H28N2O3
• Molecular Mass: 392.49072
• Monoisotopic Mass: 392.20999277
• SMILES: c1(cc2c(cc1CC)CC(C2)NC[C@H](O)c1c2c(c(cc1)O)[nH]c(=O)cc2)CC
• Canonical SMILES: CCc1cc2CC(Cc2cc1CC)NC[C@@H](c1ccc(c2c1ccc(=O)[nH]2)O)O
• 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
• InChIKey: QZZUEBNBZAPZLX-QFIPXVFZSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: indacaterol
• Synonyms: 5-[(1R)-2-[(5,6-Diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-2(1H)-quinolinone Maleic Acid; QAB 149 Maleic Acid; Onbrez; Indacaterol Maleic Acid Salt

Database IDs

• CAS Number: 753498-25-8
• PubChem SID: 164227489
• PubChem CID: 6918554

CALCULATED PROPERTIES

• Acid pKa: 8.510886
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 1.1095834
• LogD (pH = 7.4): 2.3173404
• Log P: 3.263326
• Molar Refractivity: 118.1024 cm^3
• Polarizability: 44.02345 Å^3
• Polar Surface Area: 81.59 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 195-197°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - I499750

A long-acting β2 adrenoreceptor agonist and bronchodilator, for the treatment of asthma and chronic obstructive pulmonary disease.

REFERENCES

• Currie, G.P. et al.: Curr. Opin. Invest. Drugs., 7, 457 (2006)
• Naline, E. et al.: Eur. Resp. J., 29, 575 (2006)
• Roig, J. et al.: Open Resp. Med. J., 3, 27 (2006)