1461. Bucindolol

Nomenclature

CAS number: 71119-11-4
2-[2-Hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethylethyl]amino]propoxy]benzonitrile.
C22H25N3O2; mol wt 363.45.
C 72.70%, H 6.93%, N 11.56%, O 8.80%.

Description and references

Non-selective β-adrenergic blocker with vasodilating activity. Prepn: BE 868943 (1979 to Bristol-Myers); W. E. Kreighbaum, W. T. Comer, US 4234595 (1980 to Mead Johnson); W. E. Kreighbaum et al., J. Med. Chem. 23, 285 (1980). Crystal structure: J.-M. Léger et al., Acta Crystallogr. C40, 706 (1984). Conformation: E. Coutinho, Indian J. Chem. 34B, 553 (1995). Review of chemistry and pharmacology: D. Deitchman et al., in New Drugs Annual: Cardiovascular Drugs vol. 1, A. Scriabine, Ed. (Raven Press, New York, 1983) pp 1-18. Clinical pharmacokinetics: P. A. Meredith et al, Xenobiotica 15, 979 (1985). Clinical pharmacology: N. Bett et al., Am. J. Cardiol. 57, 678 (1986). GC-MS determn in plasma: M. J. Bartek et al., J. Chromatogr. 377, 183 (1986). Evaluation in congestive heart failure: M. R. Bristow et al., Circulation 89, 1632 (1994).

Chemical structure

Properties

White crystals from abs ethanol, mp 125-127°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 70369-47-0
MJ-13105-1.
C22H25N3O2.HCl; mol wt 399.91.
C 66.07%, H 6.55%, N 10.51%, O 8.00%, Cl 8.87%.

Properties

White crystals from abs ethanol, mp 185-187°. Sol in water. Nonhygroscopic. pKa 8.86. Partition coefficient (chloroform/0.01M phosphate buffer): 83.4 (pH 7.19); 361 (pH 7.78). LD50 in mice, rats (mg/kg): ≈100, ≈100 orally (Deitchmann).

Therapeutic Category

Antihypertensive; in treatment of congestive heart failure.

Keywords

β-Adrenergic Blocker; Antihypertensive; Aryloxypropanolamine Derivatives