Canrenone

Canrenone

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
Clinical data
Trade names	Contaren, Luvion, Phanurane, Spiroletan
AHFS/Drugs.com	International Drug Names
Pharmacokinetic data
Protein binding	95%
Biological half-life	10–35 hours
Identifiers
CAS Number	976-71-6
ATC code	C03DA03 (WHO)
PubChem	CID 13789
ChemSpider	13192
UNII	78O20X9J0U
ChEMBL	CHEMBL1463345
Synonyms	RP-11614, SC-9376
Chemical data
Formula	C22H28O3
Molar mass	340.456 g/mol
SMILES O=C5\C=C4\C=C/[C@@H]1[C@H](CC[C@]3([C@H]1CC[C@]32OC(=O)CC2)C)[C@@]4(C)CC5
InChI InChI=1S/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-/m1/s1 Key:UJVLDDZCTMKXJK-WNHSNXHDSA-N
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Canrenone (INN, USAN) (brand names Contaren, Luvion, Phanurane, Spiroletan) is a steroidal antimineralocorticoid and weak antiandrogen and progestogen^[1][2] of the spirolactone group related to spironolactone which is or has been used as a diuretic in Europe, including in Italy and Belgium.^[3][4][5]

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.^[6]

Canrenone is more potent as an antimineralocorticoid relative to spironolactone, but is considerably less potent and effective as an antiandrogen.^[7][8] 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.^[9]

Canrenone has been found to be effective in the treatment of hirsutism in women.^[10]

See also

• Potassium canrenoate
• Prorenone
• Eplerenone
• Finerenone
• Drospirenone

References

1. Losert, W; Casals-Stenzel, J; Buse, M (1985). "Progestogens with antimineralocorticoid activity". Arzneimittelforschung 35 (2): 459–71. PMID 4039568.
2. Fernandez, MD; Carter, GD; Palmer, TN (1983). "The interaction of canrenone with oestrogen and progesterone receptors in human uterine cytosol". Br J Clin Pharmacol 15 (1): 95–101. doi:10.1111/j.1365-2125.1983.tb01470.x. PMC 1427833. PMID 6849751.
3. Hill, R.A.; Makin, H.L.J.; Kirk, D.N.; Murphy, G.M. (23 May 1991). Dictionary of Steroids. CRC Press. pp. 656–. ISBN 978-0-412-27060-4.
4. Romanelli, RG; Gentilini, P (May 2004). "Cross reactivity due to positive canrenone interference". Gut 53 (5): 772–3. PMC 1774040. PMID 15082604.
5. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 167–. ISBN 978-3-88763-075-1.
6. Clark, Michelle A.; Harvey, Richard A.; Finkel, Richard; Rey, Jose A.; Whalen, Karen (15 December 2011). Pharmacology. Lippincott Williams & Wilkins. pp. 286–. ISBN 978-1-4511-1314-3.
7. Coelingh Benni, H.J.T.; Vemer, H.M. (15 December 1990). Chronic Hyperandrogenic Anovulation. CRC Press. pp. 152–. ISBN 978-1-85070-322-8.
8. Seldin, Donald W.; Giebisch, Gerhard H. (23 September 1997). Diuretic Agents: Clinical Physiology and Pharmacology. Academic Press. pp. 630–. ISBN 978-0-08-053046-8.
9. Colby HD (1981). "Chemical suppression of steroidogenesis". Environ. Health Perspect. 38: 119–27. doi:10.1289/ehp.8138119. PMC 1568425. PMID 6786868.
10. Sobbrio, GA; Granata, A; Panacea, A; Trimarchi, F (1989). "Effectiveness of short term canrenone treatment in idiopathic hirsutism". Minerva Endocrinol. 14 (2): 105–8. PMID 2761494.