| Identification | Back Directory | [Name]
Canrenone | [CAS]
976-71-6 | [Synonyms]
sc9376
11614r.p
phanurane
CANRENONE
ALDADIENE
NSC 261713
CANRENONE-D4
Canrenone, >=97%
Canrenone98.5%Min
spirolactonesc14266
Journal of risperidone
CANRENOIC ACID GAMMA LACTONE
Spironolactone EP Impurity F
Eplerenone IMpurity - Canrenone
Spironolactone Related CoMpound A
CANRENONE[SPIRONOLACTONE INTERMEDIATE]
4,6-ANDROSTEN-17-ALPHA-YL-PROPIONIOACID-R-LACTONE
17-(2-Carboxyethyl)17-hydroxyandrosta-4,6-dien-3-onelactone
17-(2-Carboxyethyl)17-hydroxy-3-oxoandrosta-4,6-dienelactone
17a-2-Carboxyethyl-17-hydroxyandrosta-4,6-dien-3-one Lactone
4,6-ANDROSTADIEN[(17(B-1')-SPIRO-5')]-PERHYDROFURAN-2,3-DIONE
17-Hydroxy-3-oxo-17-pregna-4,6-diene-21-carboxylicacid-lactone
17a-(2-Carboxyethyl-17b-hydroxyandrosta-4,6-dien-3-one Lactone
(17α)-17-Hydroxy-3-oxopregna-4,6-diene-21-carboxylicacidγ-lactone
(7a)-17-Hydroxy-3-oxo-pregna-4,6-diene-21-carboxylic Acid -Lactone
PREGNA-4,6-DIENE-17-BETA-0L-3-ONE-21-CARBOXYLIC ACID-GAMMA LACTONE
(17R)-17-Hydroxy-3-oxopregna-4,6-diene-21-carboxylic acid γ-lactone
(17R)-3-Oxo-17-hydroxypregna-4,6-diene-21-carboxylic acid γ-lactone
(7a)-17-Hydroxy-3-oxo-pregna-4,6-diene-21-carboxylic Acid g-Lactone
((7 )-17-Hydroxy-3-oxo-pregna-4,6-diene-21-carboxylic Acid -Lactone)
17-hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid gamma-lactone
Pregna-4,6-diene-21-carboxylicacid, 17-hydroxy-3-oxo-, g-lactone, (17a)-
pregna-4,6-diene-21-carboxylicacid,17-hydroxy-3-oxo-,gamma-lactone,(17-alph
17-hydroxy-3-oxo-,gamma-lactone,(17-alpha)-pregna-6-diene-21-carboxylicacid
Canrenone
17-hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid gamma-lactone
Spironolactone Related Compound A (100 mg) (Canrenone (3-Oxo-17-alpha-pregna-4,6-diene-21, 17-carbolactone)) (AS)
(8R,9S,10R,13S,14S,17R)-10,13-dimethylspiro[2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione | [EINECS(EC#)]
213-554-5 | [Molecular Formula]
C22H28O3 | [MDL Number]
MFCD08064191 | [MOL File]
976-71-6.mol | [Molecular Weight]
340.46 |
| Chemical Properties | Back Directory | [Appearance]
Pale yellow to pale Green Solid | [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. ]
Store at RT | [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) |
| Hazard Information | Back Directory | [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. | [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]
Nonflammable(100%) | [Biochem/physiol Actions]
Canrenone is a mineralocorticoid (aldosterone) inhibitor. |
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