ACETYLDIGITOXIN Chemical Properties

Melting point:

217-221°

alpha 

D20 +5.0° (c = 0.7 in pyridine)

Boiling point:

673.84°C (rough estimate)

Density 

1.1009 (rough estimate)

refractive index 

1.6130 (estimate)

storage temp. 

Store at -20°C

solubility 

Chloroform: Slightly Soluble; DMSO: Slightly Soluble; Methanol: Slightly Soluble

form 

A solid

Stability:

Hygroscopic

Safety Information

RIDADR 

3249

HazardClass 

6.1(a)

PackingGroup 

II

ACETYLDIGITOXIN Usage And Synthesis

Originator

Acylanid ,Sandoz ,US ,1954

Uses

Digitoxin 3'''-Acetate is a derivative of Digitoxin (D445950) which is cardotonic.

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.

brand name

Acylanid (Novartis).

Therapeutic Function

Cardiotonic

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

ACETYLDIGITOXIN(1111-39-3)Related Product Information

• ACETYLACETICACID,SODIUMSALT
• Acetazolamide
• Acetylaconitine
• Digitoxin
• beta-acetyldigitoxin,4'''-Acetyldigitoxin
• LANATOSIDE B
• lanatoside D
• ALPHA-ACETYLDIGOXIN
• ACETYLDIGITOXIN
• Digoxin, teraacetate
• LANATOSIDE C
• LANATOSIDE A