Canrenone

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Canrenone
Skeletal formula of canrenone
Ball-and-stick model of the canrenone molecule
Systematic (IUPAC) name
10,13-dimethylspiro[2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione
Pharmacokinetic data
Protein binding 95%
Biological half-life 10-35 hours
Identifiers
CAS Registry Number 976-71-6 N
ATC code C03DA03
PubChem CID: 13789
ChemSpider 13192 YesY
UNII 78O20X9J0U YesY
ChEMBL CHEMBL1463345 N
Synonyms RP-11614, SC-9376
Chemical data
Formula C22H28O3
Molecular mass 340.456 g/mol
 N (what is this?)  (verify)

Canrenone (INN, USAN) (brand names Contaren, Luvion, Phanurane, Spiroletan) is a steroidal antimineralocorticoid and weak antiandrogen related to spironolactone which is used as a diuretic in Europe.[1][2]

Carenone is a major active metabolite of spironolactone, canrenoic acid, and potassium canrenoate, and is believed to be partially or largely responsible for their effects.[3]

Canrenone is more potent as an antimineralocorticoid relative to spironolactone, but is considerably less potent and effective as an antiandrogen.[4][5] Similarly to spironolactone, canrenone inhibits steroidogenic enzymes such as 11β-hydroxylase, cholesterol side-chain cleavage enzyme, 17α-hydroxylase, and 21-hydroxylase, but once again, is comparatively more potent in doing so.[6]

See also[edit]

References[edit]

  1. ^ R.A. Hill; H.L.J. Makin; D.N. Kirk; G.M. Murphy (23 May 1991). Dictionary of Steroids. CRC Press. pp. 656–. ISBN 978-0-412-27060-4. 
  2. ^ Romanelli RG, Gentilini P (May 2004). "Cross reactivity due to positive canrenone interference". Gut 53 (5): 772–3. PMC 1774040. PMID 15082604. 
  3. ^ Michelle A. Clark; Richard A. Harvey; Richard Finkel; Jose A. Rey, Karen Whalen (15 December 2011). Pharmacology. Lippincott Williams & Wilkins. pp. 286–. ISBN 978-1-4511-1314-3. 
  4. ^ H.J.T. Coelingh Benni; H.M. Vemer (15 December 1990). Chronic Hyperandrogenic Anovulation. CRC Press. pp. 152–. ISBN 978-1-85070-322-8. 
  5. ^ Donald W. Seldin; Gerhard H. Giebisch (23 September 1997). Diuretic Agents: Clinical Physiology and Pharmacology. Academic Press. pp. 630–. ISBN 978-0-08-053046-8. 
  6. ^ Colby HD (1981). "Chemical suppression of steroidogenesis". Environ. Health Perspect. 38: 119–27. PMC 1568425. PMID 6786868.