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HomeProduct name listCanrenone

Canrenone

Synonym(s):(17α)-17-Hydroxy-3-oxopregna-4,6-diene-21-carboxylic acid γ-lactone;Canrenone;NSC 261713

  • CAS NO.:976-71-6
  • Empirical Formula: C22H28O3
  • Molecular Weight: 340.46
  • MDL number: MFCD00071735
  • EINECS: 213-554-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-03-22 17:12:53
Canrenone Structural

What is Canrenone?

Chemical properties

Pale yellow to pale Green Solid

Originator

Spiroctan,Boehringer Mannheim,Switz.,1968

The Uses of Canrenone

Aldosterone antagonist. Diuretic

The Uses of Canrenone

antiinflammatory, glucocorticoid

The Uses of Canrenone

Inhibits aldosterone biosynthesis and blocks ouabain effects

What are the applications of Application

Canrenone is an inhibitor of aldosterone biosynthesis and ouabain

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.

Properties of Canrenone

Melting point: 158-1600C
Boiling point: 416.25°C (rough estimate)
alpha  D +24.5° (chloroform)
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
CAS DataBase Reference 976-71-6
NIST Chemistry Reference Canrenone(976-71-6)

Safety information for Canrenone

Signal word Warning
Pictogram(s)
ghs
Health Hazard
GHS08
ghs
Environment
GHS09
GHS Hazard Statements H351:Carcinogenicity
H411:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for Canrenone

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|

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