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canrenone

Structure via PubChem · Public domain (PubChem)

EntityQ5033475· pop 13· linked from 900 articles

Canrenone, sold under the brand names Contaren, Luvion, Phanurane, and Spiroletan, is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone which is used as a diuretic in Europe, including in Italy and Belgium. It is also an important active metabolite of spironolactone, and partially accounts for its therapeutic effects.

Chemical data

Formula
C22H28O3
Molecular weight
340.5 g/mol
IUPAC name
(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
SMILES
C[C@]12CCC(=O)C=C1C=C[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]45CCC(=O)O5)C
InChIKey
UJVLDDZCTMKXJK-WNHSNXHDSA-N
XLogP
2.7
Polar surface area
43.4 Ų
H-bond donors
0
H-bond acceptors
3
Formal charge
0

via PubChem

Drug data · ChEMBL

Withdrawn
Max clinical phase
Approved
Molecule type
Small molecule
Indications
cardiovascular disease

via ChEMBL · EBI

Wikidata facts

Mass
340.204
Show 5 more facts
chemical formula
C₂₂H₂₈O₃
canonical SMILES
CC12CCC(=O)C=C1C=CC3C2CCC4(C3CCC45CCC(=O)O5)C
isomeric SMILES
C[C@]12CCC(=O)C=C1C=C[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]45CCC(=O)O5)C
subject has role
antimineralocorticoid
Commons category
Canrenone
Sources (2)

via Wikidata · CC0

~4 min read

Encyclopedic overview

13 sections
Contents
  • Medical uses
  • Heart failure
  • Pharmacology
  • Pharmacodynamics
  • Pharmacokinetics
  • As a metabolite
  • History
  • Society and culture
  • Generic names
  • Brand names
  • Availability
  • See also
  • References

Canrenone, sold under the brand names Contaren, Luvion, Phanurane, and Spiroletan, is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone which is used as a diuretic in Europe, including in Italy and Belgium. It is also an important active metabolite of spironolactone, and partially accounts for its therapeutic effects.

==Medical uses== Canrenone has been found to be effective in the treatment of hirsutism in women.

Excerpted from Wikipedia’s “canrenone” article, available under the CC BY-SA 4.0 licence.