Originator
Acylanid ,Sandoz ,US ,1954
Definition
ChEBI: 3'''-O-acetyldigitoxin is a cardenolide glycoside compound consisting of digitoxin having an acetyl substituent at the 3-position on the D-ribo-hexopyranosyl residue at the non-reducing end. It has a role as an anti-arrhythmia drug, a cardiotonic drug and an enzyme inhibitor. It is functionally related to a digitoxin.
Manufacturing Process
Acetyldigitoxin-α can be obtained from acetyldigitoxin-β by heating it in an anhydrous or aqueous organic solvent at neutral, weakly acid or weakly
alkaline pH, i.e., at a pH range from about 3.5 to about 8.
The acetylidigitoxin-β used for this purpose is a cardiac glycoside which can be
obtained either by splitting off the glucose residue from lanatoside A, or by
extraction of the leaves of Digitalis ferrugines. It is composed of the aglycone
digitoxigenin and 3 molecules of digitoxose, to one of which an acetyl group is
attached. Acetyldigitoxin-α, obtained from acetyldigitoxin-β by rearrangement,
differs from the latter in the position of the acetyl group.
The process may be carried out, for example, in the following manner: A
solution of acetyldigitoxin-β in a suitable solvent, such as methanol, is boiled
under reflux and then diluted with water. The unchanged acetyldigitoxin-β,
which crystallizes out first, is filtered off and can again be submitted to the
same process. On concentrating the filtrate, acetyldigitoxin-α separates out in
crystalline form and after filtering off and recrystallizing is obtained in a pure
state. The acetyldigitoxin-α crystallizes from aqueous methanol in platelets
melting at 217-221°C.
Purification Methods
-Acetyldigitoxin is obtained from the commercial mixture [ : (2:1)] [25395-32-8]. The form is obtained from the form by heating in anhydrous or aqueous organic solvent (e.g. aqueous MeOH) at pH 3.5—8. It crystallises from MeOH as plates, CHCl3/Et2O or Me2CO/Et2O. At 20o 1g dissolves in 16mL of MeOH, 66mL of Me2CO and ~880mL of EtOAc. [Stoll & Kreis Helv Chim Acta 35 1318, 1322 1952, Beilstein 18 III/IV 1479.] It is a cardenolide.C5128
