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
3D model (Jmol)	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 ;
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カンレノン

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/11/12 21:07:57」(JST)

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Canrenone (INN, USAN) (brand names Contaren, Luvion, Phanurane, Spiroletan), also known as aldadiene,^[1] is a steroidal antimineralocorticoid and weak antiandrogen and progestogen^[2]^[3] of the spirolactone group related to spironolactone which is or has been used as a diuretic in Europe, including in Italy and Belgium.^[4]^[5]^[6]

Canrenone is an active metabolite of spironolactone, canrenoic acid, and potassium canrenoate, and is believed to be partially or largely responsible for their effects (depending on the drug in question).^[7]

Canrenone is more potent as an antimineralocorticoid relative to spironolactone, but is considerably less potent and effective as an antiandrogen.^[8]^[9] 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 less potent in doing so.^[10]

Canrenone has been found to be effective in the treatment of hirsutism in women.^[11]

References

^ Jürg Müller (6 December 2012). Regulation of Aldosterone Biosynthesis: Physiological and Clinical Aspects. Springer Science & Business Media. pp. 164–. ISBN 978-3-642-83120-1.
^ Losert, W; Casals-Stenzel, J; Buse, M (1985). "Progestogens with antimineralocorticoid activity". Arzneimittelforschung. 35 (2): 459–71. PMID 4039568.
^ 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.
^ 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.
^ Romanelli, RG; Gentilini, P (May 2004). "Cross reactivity due to positive canrenone interference". Gut. 53 (5): 772–3. PMC 1774040. PMID 15082604.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 167–. ISBN 978-3-88763-075-1.
^ 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.
^ Coelingh Benni, H.J.T.; Vemer, H.M. (15 December 1990). Chronic Hyperandrogenic Anovulation. CRC Press. pp. 152–. ISBN 978-1-85070-322-8.
^ 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.
^ Colby HD (1981). "Chemical suppression of steroidogenesis". Environ. Health Perspect. 38: 119–27. doi:10.1289/ehp.8138119. PMC 1568425. PMID 6786868.
^ 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.

UpToDate Contents

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1. 男性型多毛症の治療 treatment of hirsutism

English Journal

Stability and removal of spironolactone from wastewater.

Sulaiman S1, Khamis M, Nir S, Lelario F, Scrano L, Bufo SA, Karaman R.
Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering.J Environ Sci Health A Tox Hazard Subst Environ Eng.2015 Sep 19;50(11):1127-35. doi: 10.1080/10934529.2015.1047668.
Stability and removal of spironolactone (SP) from wastewater produced at Al-Quds University Campus were investigated. Kinetic studies on both pure water and wastewater coming from secondary treatment (activated sludge) demonstrated that the potassium-sparing diuretic (water pill), spironolactone, un
PMID 26191987

Marinobufagenin-induced vascular fibrosis is a likely target for mineralocorticoid antagonists.

Fedorova OV1, Emelianov IV, Bagrov KA, Grigorova YN, Wei W, Juhasz O, Frolova EV, Marshall CA, Lakatta EG, Konradi AO, Bagrov AY.
Journal of hypertension.J Hypertens.2015 Aug;33(8):1602-10. doi: 10.1097/HJH.0000000000000591.
OBJECTIVE: Endogenous cardiotonic steroids, including marinobufagenin (MBG), stimulate vascular synthesis of collagen. Because mineralocorticoid antagonists competitively antagonize effect of cardiotonic steroids on the Na/K-ATPase, we hypothesized that spironolactone would reverse the profibrotic e
PMID 26136067

Ammonium increases Ca(2+) signalling and upregulates expression of Cav1.2 gene in astrocytes in primary cultures and in the in vivo brain.

Wang F1, Du T1, Liang C1, Verkhratsky A2,3,4, Peng L1.
Acta physiologica (Oxford, England).Acta Physiol (Oxf).2015 Jun;214(2):261-74. doi: 10.1111/apha.12500. Epub 2015 Apr 18.
AIM: The primary aim of this study was to identify the effects of hyperammonaemia on functional expression of Cav1.2 L-type Ca(2+) channels in astroglia.METHODS: Primary cultures of mouse astrocytes were used to study effects of chronic treatment (1-5 days) with ammonium chloride, at 1, 3 and 5 mm o
PMID 25846713

Japanese Journal

Polyuric-polydipsic syndrome in a pediatric case of non-glucocorticoid remediable familial hyperaldosteronism

Endocrine journal 59(6), 497-502, 2012-06-01
NAID 10030816811

Development and validation of a dried blood spot-LC-APCI-MS assay for estimation of canrenone in paediatric samples

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 878(9), 769-776, 2010-03-15
NAID 10028033716

Development and validation of an HPLC method for the determination of spironolactone and its metabolites in paediatric plasma samples

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 839(1), 36-44, 2006-07-24
NAID 10025785203

v t e Mineralocorticoids and antimineralocorticoids (H02)

Mineralocorticoids	11-Deoxycorticosterone (desoxycortone) 11-Deoxycortisol (cortodoxone) Aldosterone Corticosterone Cortisol (hydrocortisone) Desoxycortone acetate Desoxycortone enanthate Fludrocortisone Fludrocortisone acetate

Antimineralocorticoids	Steroidal: Canrenoate potassium (potassium canrenoate) Canrenoic acid Canrenone Drospirenone Dydrogesterone Eplerenone Gestodene Progesterone Quingestrone Spironolactone Non-steroidal: Amlodipine Benidipine Felodipine Finerenone Nifedipine Nimodipine Nitrendipine

Synthesis modifiers	Acetoxolone Aminoglutethimide Carbenoxolone Enoxolone Ketoconazole Metyrapone Mitotane Trilostane

^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III See also: Androgens and antiandrogens • Estrogens and antiestrogens • Progestogens and antiprogestogens • Glucocorticoids and antiglucocorticoids

v t e Steroid hormone metabolism modulators

HMGCR	Inhibitors: Atorvastatin Cerivastatin Fluvastatin Lovastatin Mevastatin Pitavastatin Pravastatin Rosuvastatin Simvastatin

FPS	Inhibitors: Alendronic acid Clodronic acid Etidronic acid Ibandronic acid Incadronic acid Pamidronic acid Risedronic acid Tiludronic acid Zoledronic acid

24-DHCR24	20,25-Diazacholesterol Clomifene Triparanol

20,22-Desmolase (P450scc)	Inhibitors: 22-ABC 3,3′-Dimethoxybenzidine 3-Methoxybenzidine Aminoglutethimide Canrenone Cyanoketone Danazol Etomidate Ketoconazole Mitotane Spironolactone Trilostane

17α-Hydroxylase, 17,20-Lyase	Inhibitors: 22-ABC 22-Oxime Δ⁴-Abiraterone Abiraterone Abiraterone acetate Amphenone Bifluranol Bifonazole Canrenone CFG-920 Clotrimazole Cyanoketone Cyproterone acetate Danazol Econazole Flutamide Galeterone Gestrinone Isoconazole Ketoconazole L-39 Levoketoconazole Liarozole LY-207,320 MDL-27,302 Miconazole Mifepristone Nilutamide Orteronel Pioglitazone Prochloraz Rosiglitazone Seviteronel Spironolactone Stanozolol SU-9055 SU-10603 TGF-β Tioconazole Troglitazone VN/87-1 YM116

3α-HSD	Inhibitors: Coumestrol Daidzein Genistein Indomethacin Medroxyprogesterone acetate Inducers: Fluoxetine Fluvoxamine Mirtazapine Paroxetine Sertraline Venlafaxine

3β-HSD	Inhibitors: 4-MA Δ⁴-Abiraterone Abiraterone Abiraterone acetate Azastene Cyanoketone Cyproterone acetate Danazol Epostane Genistein Gestrinone Medrogestone Medroxyprogesterone acetate Metyrapone Norethisterone Oxymetholone Pioglitazone Rosiglitazone Trilostane Troglitazone

11β-HSD	Inhibitors: 11α-Hydroxyprogesterone 11β-Hydroxyprogesterone 18α-Glycyrrhizic acid ABT-384 Acetoxolone Carbenoxolone Enoxolone (glycyrrhetinic acid) Epigallocatechin gallate Glycyrrhizin (glycyrrhizic acid) Progesterone

21-Hydroxylase	Inhibitors: Aminoglutethimide Amphenone B Bifonazole Canrenone Clotrimazole Diazepam Econazole Genistein Isoconazole Ketoconazole Levoketoconazole Metyrapone Miconazole Midazolam Spironolactone Tioconazole

11β-Hydroxylase	Inhibitors: Δ⁴-Abiraterone Abiraterone Abiraterone acetate Aminoglutethimide Canrenone Etomidate Fadrozole FETO Ketoconazole Levoketoconazole Metomidate Metyrapol Metyrapone Mitotane Potassium canrenoate Spironolactone Trilostane

18-Hydroxylase	Inhibitors: 18-Ethynylprogesterone (18-ethinylprogesterone) 18-Vinylprogesterone Aminoglutethimide Canrenone FAD286 Fadrozole Ketoconazole LCI699 Metyrapone Mespirenone Potassium canrenoate Spironolactone

17β-HSD	Inhibitors: Danazol Simvastatin

5α-Reductase	Inhibitors: 22-Oxime Δ⁴-Abiraterone Abiraterone Abiraterone acetate Alfatradiol Azelaic acid β-Sitosterol Bexlosteride Chlormadinone acetate Cl-4AS-1 Dutasteride Epitestosterone Epristeride Fatty acids (α-linolenic acid, linoleic acid, γ-linolenic acid, monolinolein, oleic acid) Finasteride Ganoderic acid Gestodene Izonsteride L-39 Lapisteride Oxendolone Saw palmetto TFM-4AS-1 Turosteride Vitamin B6 Zinc

Aromatase	Inhibitors: 4-AT 4-Cyclohexylaniline 4-Hydroxytestosterone 5α-DHNET 20α-Dihydroprogesterone Abyssinone II Aminoglutethimide Anastrozole Ascorbic acid (vitamin C) Atamestane ATD Bifonazole CGP-45,688 CGS-47,645 Chalconoids (e.g., isoliquiritigenin) Clotrimazole Corynesidone A Coumestrol DHT Difeconazole Econazole Ellagitannins Endosulfan Exemestane Fadrozole Fatty acids (e.g., conjugated linoleic acid, linoleic acid, linolenic acid, palmitic acid) Fenarimol Finrozole Flavonoids (e.g., 7-hydroxyflavone, 7-hydroxyflavanone, 7,8-DHF, acacetin, apigenin, baicalein, biochanin A, chrysin, EGCG, gossypetin, hesperetin, liquiritigenin, myricetin, naringenin, pinocembrin, rotenone, quercetin, sakuranetin, tectochrysin) Formestane Imazalil Isoconazole Ketoconazole Letrozole Liarozole Melatonin MEN-11066 Miconazole Minamestane Nimorazole NKS01 Norendoxifen ORG-33,201 Penconazole Phenytoin Prochloraz PGE2 (dinoprostone) Plomestane Prochloraz Propioconazole Pyridoglutethimide Quinolinoids (e.g., berberine, casimiroin, triptoquinone A, XHN22, XHN26, XHN27) Resorcylic acid lactones (e.g., zearalenone) Rogletimide Stilbenoids (e.g., resveratrol) Talarozole Terpenoids (e.g., dehydroabietic acid, (–)-dehydrololiolide, retinol (vitamin A), Δ⁹-THC, tretinoin) Testolactone Tioconazole Triadimefon Triadimenol Troglitazone Valproic acid Vorozole Xanthones (e.g., garcinone D, garcinone E, α-mangostin, γ-mangostin, monodictyochrome A, monodictyochrome B) YM-511 Zinc Inducers: Atrazine Flavonoids (e.g., genistein, quercetin)

SST/EST	4′OH-CB79 6-Hydroxyflavone 2,6-Dichloro-4-nitrophenol (DCNP) Equol Galangin Genistein Parabens (e.g., butylparaben) Pentachlorophenol (PCP) Triclosan

STS	AHBS Danazol Estrone-3-O-sulfamate (EMATE) Irosustat (STX64, 667 Coumate, BN-83495) KW-2581 Progestogens SR-16157 STX213 STX681 STX1938

27-Hydroxylase	Inhibitors: Anastrozole Bicalutamide Dexmedetomidine Fadrozole Posaconazole Ravuconazole

Others	Inhibitors: Inhibit estradiol degradation: Cimetidine

See also: Androgenics • Estrogenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics

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