Canrenone Chemical Properties

Melting point:

158-1600C

alpha 

D +24.5° (chloroform)

Boiling point:

416.25°C (rough estimate)

Density 

1.1236 (rough estimate)

refractive index 

1.5000 (estimate)

storage temp. 

room temp

solubility 

DMSO: soluble20mg/mL, clear

form 

powder

color 

white to beige

optical activity

[α]/D +17 to +24°, c = 1 in chloroform-d

Water Solubility 

272.4ug/L(25 ºC)

InChI

InChI=1/C22H28O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h3-4,13,16-18H,5-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/s3

InChIKey

UJVLDDZCTMKXJK-MUWITHSMNA-N

SMILES

[C@@]12(CCC(=O)O1)CC[C@@]1([H])[C@]3([H])C=CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]21C |&1:0,8,10,20,22,26,r|

LogP

2.54 at 25℃

CAS DataBase Reference

976-71-6

NIST Chemistry Reference

Canrenone(976-71-6)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

40-51/53

Safety Statements 

36/37-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HS Code 

29329990

Canrenone Usage And Synthesis

Chemical Properties

Pale yellow to pale Green Solid

Originator

Spiroctan,Boehringer Mannheim,Switz.,1968

Uses

Aldosterone antagonist. Diuretic

Uses

antiinflammatory, glucocorticoid

Uses

Inhibits aldosterone biosynthesis and blocks ouabain effects

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.

brand name

Luvion.

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

Non flammable

Biological Activity

Mineralocorticoid receptor antagonist. Active metabolite of spironolactone ((7a,17a)-7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid g-lactone ).

Biochem/physiol Actions

Canrenone is a mineralocorticoid (aldosterone) inhibitor.

Canrenone(976-71-6)Related Product Information

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