Canrenone

Canrenone
Clinical data
Trade names	Contaren, Luvion, Phanurane, Spiroletan
Other names	Aldadiene; SC-9376; RP-11614; 7α-Desthioacetyl-δ6-spironolactone; 6,7-Dehydro-7α-desthioacetylspironolactone; 17-Hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid γ-lactone
AHFS/Drugs.com	International Drug Names
Drug class	Antimineralocorticoid
ATC code	C03DA03 (WHO) ;
Pharmacokinetic data
Protein binding	95%
Elimination half-life	16.5 hours
Identifiers
	IUPAC name 10,13-Dimethylspiro[2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione;
CAS Number	976-71-6 ;
PubChem CID	13789;
ChemSpider	13192 ;
UNII	78O20X9J0U;
ChEMBL	ChEMBL1463345 ;
CompTox Dashboard (EPA)	DTXSID3045930 ;
ECHA InfoCard	100.012.322
Chemical and physical data
Formula	C22H28O3
Molar mass	340.463 g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
	(what is this?) (verify)

Canrenone, sold under the brand names Contaren, Luvion, Phanurane, and Spiroletan, is a steroidal antimineralocorticoid^[3]^[4] of the spirolactone group related to spironolactone which is used as a diuretic in Europe, including in Italy and Belgium.^[5]^[6]^[7]^[8] It is also an important active metabolite of spironolactone, and partially accounts for its therapeutic effects.^[9]^[2]

^ Müller J (6 December 2012). Regulation of Aldosterone Biosynthesis: Physiological and Clinical Aspects. Springer Science & Business Media. pp. 164–. ISBN 978-3-642-83120-1.
^ ^a ^b Gardiner P, Schrode K, Quinlan D, Martin BK, Boreham DR, Rogers MS, et al. (April 1989). "Spironolactone metabolism: steady-state serum levels of the sulfur-containing metabolites". Journal of Clinical Pharmacology. 29 (4): 342–347. doi:10.1002/j.1552-4604.1989.tb03339.x. PMID 2723123. S2CID 29457093.
^ Losert W, Casals-Stenzel J, Buse M (1985). "Progestogens with antimineralocorticoid activity". Arzneimittel-Forschung. 35 (2): 459–471. PMID 4039568.
^ Fernandez MD, Carter GD, Palmer TN (January 1983). "The interaction of canrenone with oestrogen and progesterone receptors in human uterine cytosol". British Journal of Clinical Pharmacology. 15 (1): 95–101. doi:10.1111/j.1365-2125.1983.tb01470.x. PMC 1427833. PMID 6849751.
^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 210–. ISBN 978-1-4757-2085-3.
^ Hill R, Makin H, Kirk D, Murphy G (23 May 1991). Dictionary of Steroids. CRC Press. pp. 656–. ISBN 978-0-412-27060-4.
^ Romanelli RG, Gentilini P (May 2004). "Cross reactivity due to positive canrenone interference". Gut. 53 (5): 772–773. PMC 1774040. PMID 15082604.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 167–. ISBN 978-3-88763-075-1.
^ Cite error: The named reference ClarkHarvey2011 was invoked but never defined (see the help page).

[Müller2012-1] Müller J (6 December 2012). Regulation of Aldosterone Biosynthesis: Physiological and Clinical Aspects. Springer Science & Business Media. pp. 164–. ISBN 978-3-642-83120-1.

[pmid2723123-2] Gardiner P, Schrode K, Quinlan D, Martin BK, Boreham DR, Rogers MS, et al. (April 1989). "Spironolactone metabolism: steady-state serum levels of the sulfur-containing metabolites". Journal of Clinical Pharmacology. 29 (4): 342–347. doi:10.1002/j.1552-4604.1989.tb03339.x. PMID 2723123. S2CID 29457093.

[pmid4039568-3] Losert W, Casals-Stenzel J, Buse M (1985). "Progestogens with antimineralocorticoid activity". Arzneimittel-Forschung. 35 (2): 459–471. PMID 4039568.

[pmid6849751-4] Fernandez MD, Carter GD, Palmer TN (January 1983). "The interaction of canrenone with oestrogen and progesterone receptors in human uterine cytosol". British Journal of Clinical Pharmacology. 15 (1): 95–101. doi:10.1111/j.1365-2125.1983.tb01470.x. PMC 1427833. PMID 6849751.

[Elks2014-5] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 210–. ISBN 978-1-4757-2085-3.

[HillMakin1991-6] Hill R, Makin H, Kirk D, Murphy G (23 May 1991). Dictionary of Steroids. CRC Press. pp. 656–. ISBN 978-0-412-27060-4.

[pmid15082604-7] Romanelli RG, Gentilini P (May 2004). "Cross reactivity due to positive canrenone interference". Gut. 53 (5): 772–773. PMC 1774040. PMID 15082604.

[IndexNominum2000-8] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 167–. ISBN 978-3-88763-075-1.

[ClarkHarvey2011-9] Cite error: The named reference ClarkHarvey2011 was invoked but never defined (see the help page).

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]