Chemical Properties
Pale yellow to pale Green Solid
Uses
Aldosterone antagonist. Diuretic
Uses
antiinflammatory, glucocorticoid
Biological Activity
Mineralocorticoid receptor antagonist. Active metabolite of spironolactone ((7a,17a)-7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid g-lactone ).
Originator
Spiroctan,Boehringer
Mannheim,Switz.,1968
Definition
ChEBI:Canrenone is a steroid lactone.
Manufacturing Process
The lactone is prepared as follows: A solution of 5 parts of 17α-carboxyethyl-
17β-hydroxyandrost-4-en-3-one lactone and 5 parts of chloranil in 400 parts
of xylene containing a trace of p-toluenesulfonic acid is heated at the boiling
point of the solvent under reflux overnight. The solution is then cooled and
filtered through approximately 200 parts of silica gel. The gel is successively
washed with 5%, 10%, and 15% ethyl acetate-benzene solutions, and the
washings comprising 15% ethyl acetate are thereupon purified by
chromatography on a further quantity of silica gel, using benzene and ethyl
acetate as developing solvents. From the 15% ethyl acetate eluate there is
obtained pure 17α-carboxyethyl-17β-hydroxyandrost-4,6-dien-3-one lactone,
melting at 148° to 151°C. The product solidifies above this melting point and
melts again at 165°C.
Therapeutic Function
Aldosterone antagonist, Diuretic
World Health Organization (WHO)
Canrenone, which has aldosterone antagonist activity, is a major
metabolite of spironolactone and the major metabolite of potassium canrenoate.
See WHO comments for potassium canrenoate and spironolactone.
Flammability and Explosibility
Nonflammable(100%)
Biochem/physiol Actions
Canrenone is a mineralocorticoid (aldosterone) inhibitor.
