BETA-ACETYLDIGOXIN

Chemical Properties

White Solid

Originator

Novodigal ,Asta Medica Arzneimittel

Uses

Digoxin derivative, a cardiotonic glycosides

Definition

ChEBI: Acetyldigoxin is a cardenolide glycoside.

Manufacturing Process

Dried crude product of the partial acetylation of digoxin (42 g) prepared from digitalis - is dissolved under reflux in acetone (480 ml) and n-hexane (2400 ml) is added to the solution with stirring. Fine crystals, which begin to separate immediately, are left at room temperature for 5 hours, then they are filtered with suction, washed with n-hexane and dried in vacuum at 40°C, yielding 32 g of crude β-acetyldigoxin (product 1). Product 1 (31 g) is dissolved under reflux in chloroform (500 ml) and toluene (2500 ml) is added thereto with stirring. The crystals, which separate after standing for 6 hours at room temperature, are filtered, washed with toluene and ether and dried in vacuum yielding 29 g of β-acetyldigoxin (product 2). MP: 249°-251°C.
The filtrate, which results from the separation of product 1, is evaparated to dryness in vacuum. The residue, which mainly contains unreacted digoxin, is purified by recrystallization from pyridine/ether/water (3.5:5:40) and repeatedly acetylated. It can then be recycled to produce more β- acetyldigoxin. The filtrate resulting from the separation of product 2 is evaporated to dryness. The resulting residue contains the di- and polyacetyl derivatives of digoxin, which are deacetylated to digoxin in a known manner and later is returned to a further acetylation process and can then be recycled to produce more β-acetyldigoxin. Beta-Acetyldigoxin may be prepared from digoxin, acetic acid and dicyclohexylcarbodiimide using the last one as a condensing agent.

Therapeutic Function

Cardiotonic