6562. Nipradilol

Nomenclature

CAS number: 81486-22-8
3,4-Dihydro-8-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-2H-1-benzopyran-3-ol 3-nitrate; 3,4-dihydro-8-(2-hydroxy-3-isopropylamino)propoxy-3-nitroxy-2H-1-benzopyran; 8-[2-hydroxy-3-(isopropylamino)propoxy]-3-chromanol 3-nitrate; nipradolol; K-351; Hypadil (Kowa).
C15H22N2O6; mol wt 326.34.
C 55.21%, H 6.79%, N 8.58%, O 29.42%.

Description and references

β-Adrenergic blocker with vasodilating activity. Prepn: M. Shiratsuchi et al., EP 42299; eidem, US 4394382 (1981, 1983 both to Kowa). Synthesis: M. Shiratsuchi et al., Chem. Pharm. Bull. 35, 632 (1987). Resolution of isomers: M. Shiratsuchi et al., EP 154511; eidem, US 4727085 (1985, 1988 both to Kowa). Synthesis and activity of isomers: M. Shiratsuchi et al., Chem. Pharm. Bull. 35, 3691 (1987). Pharmacology: Y. Uchida et al., Arch. Int. Pharmacodyn. 262, 132 (1983). Hemodynamic effects in dogs: H. Hisa et al., ibid. 271, 169 (1984). Effects on cardiac function in dogs: M. Sakanashi et al., ibid. 274, 47 (1985); M. Fujii et al., Jpn. Heart J. 27, 233 (1986). Pharmacokinetics and metabolism in rats: S. Kabuto et al., Arzneim.-Forsch. 35, 1674 (1985); H. Kimata et al., ibid. 1680. Metabolic fate in dog and man: M. Yoshimura et al., Chem. Pharm. Bull. 33, 3456 (1985). Clinical evaluation in angina: H. Kishida et al., Jpn. Heart J. 29, 309 (1988).

Chemical structure

Properties

Colorless needles, mp 107-116° (Shiratsuchi, 1983); also reported as mp 110-122° (Shiratsuchi, 1987). LD50 i.v. in mice, rats: 74.0, 73.0 mg/kg; orally in mice: 540 mg/kg (Shiratsuchi, 1988).

Therapeutic Category

Antianginal; antihypertensive.

Keywords

β-Adrenergic Blocker; Antianginal; Antihypertensive; Aryloxypropanolamine Derivatives