7735. Prenalterol

Nomenclature

CAS number: 57526-81-5
4-[(2S)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]phenol; (-)-(S)-1-(p-hydroxyphenoxy)-3-(isopropylamino)-2-propanol.
C12H19NO3; mol wt 225.28.
C 63.98%, H 8.50%, N 6.22%, O 21.31%.

Description and references

A β1-adrenergic agonist. Prepn: K. A. Jaeggi et al., DE 2503968 corresp to US 3978041 and US 4049797 (1974, 1976, 1977, all to Ciba-Geigy). Pharmacologic study: E. Carlsson et al., Arch. Pharmacol. 300, 101 (1977). Metabolism, hemodynamic effects, pharmacokinetics in man: O. R"onn et al., Eur. J. Clin. Pharmacol. 17, 81 (1980). Cardiovascular effects: D. H. Scott et al., Br. J. Clin. Pharmacol. 7, 365 (1979). Clinical study in coronary heart disease: I. Hutton et al., Br. Heart J. 43, 134 (1980). See also T. P. Kenakin, D. Beek, J. Pharmacol. Exp. Ther. 213, 406 (1980) for a discussion of the selectivity of action. Prepns of the racemic mixture: NL 6409883 corresp to H. K"oppe et al., US 3637852 (1965, 1972 both to Boehringer, Ing.); NL 301580 corresp to A. F. Crowther, L. H. Smith, US 3501769 (1965, 1970 both to ICI); A. F. Crowther et al., J. Med. Chem. 12, 638 (1969). Symposium: Acta Med. Scand. Suppl. 659, 1-325 (1982).

Chemical structure

Properties

Crystals from ethyl acetate, mp 127-128°. [α]D20 -1 ±1°; [α]20Hg +2 ±1° (c = 0.940 in methanol).

Derivative

Hydrochloride.

Nomenclature

CAS number: 61260-05-7
H-133/22; CGP-7760B; (-)H-80/62; Hyprenan (Astra).
C12H19NO3.HCl; mol wt 261.75.
C 55.06%, H 7.70%, N 5.35%, O 18.34%, Cl 13.54%.

Therapeutic Category

Cardiotonic.

Keywords

β-Adrenergic Agonist; Cardiotonic