Canrenone

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Names

[ CAS No. ]:
976-71-6

[ Name ]:
Canrenone

[Synonym ]:
Phanurane
Luvion
ALDADIENE
(17a)-17-Hydroxy-3-oxopregna-4,6-diene-21-carboxylic acid g-lactone
17a-(2-Carboxyethyl)-17b-hydroxyandrosta-4,6-dien-3-one Lactone
Canrenone
Spiro[17H-cyclopenta[a]phenanthrene-17,2'(5'H)-furan]-3,5'(2H)-dione, 1,3',4',8,9,10,11,12,13,14,15,16-dodecahydro-10,13-dimethyl-, (8R,9S,10R,13S,14S,17R)-
17a-(2-Carboxyethyl)-17b-hydroxy-3-oxoandrosta-4,6-diene Lactone
3-(3-Oxo-17b-hydroxy-4,6-androstadien-17a-yl)propionic Acid g-Lactone
Contaren
6-Dehydrotestosterone-17a-propionic Acid g-Lactone
CANRENONE-D4
(8R,9S,10R,13S,14S,17R)-10,13-Dimethyl-1,8,9,10,11,12,13,14,15,16-decahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-3,5'(2H,4'H)-dione
11614 R.P.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
541.1±50.0 °C at 760 mmHg

[ Melting Point ]:
158-160ºC

[ Molecular Formula ]:
C₂₂H₂₈O₃

[ Molecular Weight ]:
340.456

[ Flash Point ]:
237.6±30.2 °C

[ Exact Mass ]:
340.203857

[ PSA ]:
43.37000

[ LogP ]:
2.99

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.581

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TU3493000

CHEMICAL NAME :: Pregna-4,6-diene-21-carboxylic acid, 17-hydroxy-3-oxo-, gamma-lactone, (17-alpha)-

CAS REGISTRY NUMBER :: 976-71-6

BEILSTEIN REFERENCE NO. :: 0046602

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C22-H28-O3

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ATDAEI Acute Toxicity Data. Journal of the American College of Toxicology, Part B. (Mary Ann Liebert, Inc., 1651 Third Ave., New York, NY 10128) V.1- 1990- Volume(issue)/page/year: 1,36,1990

Safety Information

[ Symbol ]:

GHS08, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H351-H411

[ Precautionary Statements ]:
P280

[ Hazard Codes ]:
Xn,N

[ Risk Phrases ]:
40-51/53

[ Safety Phrases ]:
36/37-61

[ RIDADR ]:
UN 3077 9 / PGIII

[ HS Code ]:
29329990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

7alpha-Thiospironolactone
3-oxopregn-4-ene-21,17alpha-carbolactone
Spironolactone
Ethisterone
5'-hydroxyspiro[pregnane-17,2'-tetrahydrofuran]-5-en-3-one
methyl iodide
3β,17α-dihydroxypregn-5-ene-21-carboxylic acid γ-lactone

DownStream

7α-Thiomethyl Spironolactone
7β-Spironolactone
Spironolactone
11α-Hydroxy Canrenone
(1R,8S,9S,10R,11R,13S,14S,17R)-1,11-dihydroxy-10,13-dimethyl-1,3',4',8,9,10,11,12,13,14,15,16-dodecahydro-5'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-3,5'(2H)-dione
Riforal

Articles

Aldosterone receptor blockers spironolactone and canrenone: two multivalent drugs.

Expert Opin. Pharmacother. 15(7) , 909-12, (2014)

Canrenone is a derivative of spironolactone with lower antiandrogen activity. The drug is used only in few countries and can block all the side effects of aldosterone (ALDO). The drug is effective eve...

Additional use of an aldosterone antagonist in patients with mild to moderate chronic heart failure: a systematic review and meta-analysis.

Br. J. Clin. Pharmacol. 75(5) , 1202-12, (2013)

Aldosterone antagonists (AldoAs) have been used to treat severe chronic heart failure (CHF). There is uncertainty regarding the efficacy of using AldoAs in mild to moderate CHF with New York Heart Ass...

The effects of canrenone on inflammatory markers in patients with metabolic syndrome.

Ann. Med. 47(1) , 47-52, (2015)

To evaluate the effects of canrenone compared to placebo on blood pressure control, some non-conventional biomarkers in cardiovascular stratification, and on metalloproteinases in patients affected by...

CanrenoneMin
delta-9,11-Canrenone
11α-Hydroxy Canrenone
6,7-Dihydro Canrenone Lactol
11-A-Hydroxy canrenone methyl ester
2,6-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one
N-(1-{[(1-cyano-1-methylethyl)(methyl)carbamoyl]methyl}piperidin-4-yl)-5-methylthiophene-2-carboxamide
N-[(Ethylamino)carbonyl]-2-[(4-fluorophenyl)amino]propanamide
Butyl-[2-[4-(sec-butylthio)phenyl]imidazo[1,2-a]pyrazin-3-yl]amine
3,4-(Methylenedioxy-d2)-aniline
3-Methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole-6-carboxylic acid
4-Fluoro-N-[4-(4-methoxyphenethyl)-3-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-YL]benzamide
4-Formyl-2-(trifluoromethyl)biphenyl
4,4-Dimethyl-2-oxotetrahydrofuran-3-carboxylic acid
N-(3,4-dichlorophenyl)-N-ethyl-3-(1-methylpiperidin-4-yl)-propionamide

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