8-hydroxy-5-{1-hydroxy-2-[(propan-2-yl)amino]butyl}-1,2-dihydroquinolin-2-one hydrochloride

• ChemBase ID: 179726
• Molecular Formular: C16H23ClN2O3
• Molecular Mass: 326.81842
• Monoisotopic Mass: 326.13972029
• SMILES: c12c([nH]c(=O)cc2)c(ccc1C(C(NC(C)C)CC)O)O.Cl
• Canonical SMILES: CCC(C(c1ccc(c2c1ccc(=O)[nH]2)O)O)NC(C)C.Cl
• InChI: InChI=1S/C16H22N2O3.ClH/c1-4-12(17-9(2)3)16(21)11-5-7-13(19)15-10(11)6-8-14(20)18-15;/h5-9,12,16-17,19,21H,4H2,1-3H3,(H,18,20);1H
• InChIKey: AEQDBKHAAWUCMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-hydroxy-5-{1-hydroxy-2-[(propan-2-yl)amino]butyl}-1,2-dihydroquinolin-2-one hydrochloride
• IUPAC Traditional name: 8-hydroxy-5-{1-hydroxy-2-[(propan-2-yl)amino]butyl}-1,2-dihydroquinolin-2-one hydrochloride
• Synonyms: Procaterol Hydrochloride

Database IDs

• CAS Number: 72332-33-3
• PubChem SID: 164235636
• PubChem CID: 656601

CALCULATED PROPERTIES

• Acid pKa: 8.519182
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -1.2235061
• LogD (pH = 7.4): -0.0811332
• Log P: 0.88412946
• Molar Refractivity: 84.5808 cm^3
• Polarizability: 31.786533 Å^3
• Polar Surface Area: 81.59 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: A long-acting beta-2 Adrenergic receptor agonist; Bronchodilator; Sympathomimetic

Product Information

• Salt Data: HCl
• Application(s): Bronchodilator agent; Sympathomimetic

REFERENCES

• Yoshizaki, S. et al., J. Med. Chem., 1976, 19, 1138; 1977, 20, 1103, (synth, pharmacol, isom)
• Shimizu, T. et al., Xenobiotica, 1978, 8, 705, (metab)
• Kido, M. et al., Chem. Pharm. Bull., 1982, 30, 44, (cryst struct, bibl)
• Wright, D.S. et al., J. Chromatogr., 1987, 417, 223, (hplc)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4089
• Yoshizaki, S. et al., Chem. Pharm. Bull., 1993, 41, 1305, (sar)
• Yamaguchi, M. et al., J. Asthma, 1995, 32, 125, (pharmacol)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1587
• Yoshimura, T. et al., Pharmacology, 1997, 54, 144, (pharmacol)