CANRENONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H28O3
Molecular Weight	340.4559
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]4([H])[C@@]2([H])C=CC5=CC(=O)CC[C@]45C

InChI

InChIKey=UJVLDDZCTMKXJK-WNHSNXHDSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H28O3
Molecular Weight	340.4559
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2761494 | http://www.my-personaltrainer.it/Foglietti-illustrativi/Luvion.html | https://www.ncbi.nlm.nih.gov/pubmed/25319120

Canrenone, a spironolactone metabolite, is a mineralocorticoid receptor antagonist. Canrenone is used as a diuretic in Europe and, in particular, in Italy under brand name Luvion. Luvion is a tablet for oral application which is effective for the treatment Hyperaldosteronism primary, secondary hyperaldosteronism from edematous states ( heart failure congestive, cirrhosis of the liver in phase ascites , nephrotic syndrome ) and arterial hypertension essential where other therapies were not sufficiently effective or tolerate. In addition was suggested that canrenone might represent an effective therapy for idiopathic post-puberal hirsutism and it normalizds the cardiac response to the postural challenge in patients with preascitic cirrhosis. Canrenone seems to be effective in reducing blood pressure in patients with metabolic syndrome. Moreover, canrenone seems also to improve MPO, Lp(a), and metalloproteinases in these patients.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mineralocorticoid receptor 53 Target ID: P08235 Gene ID: 4306.0 Gene Symbol: NR3C2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/4280522	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Hyperaldosteronism 1 Sources: http://www.my-personaltrainer.it/Foglietti-illustrativi/Luvion.html	Palliative	Approved 8429	Luvion Approved Use Unknown
Arterial hypertension 5 Sources: http://www.my-personaltrainer.it/Foglietti-illustrativi/Luvion.html	Palliative	Approved 8429	Luvion Approved Use Unknown
Idiopathic hirsutism 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2761494	Palliative	Not Provided 504	Unknown Approved Use Unknown
Metabolic syndrome 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25319120	Palliative	Not Provided 504	Unknown Approved Use Unknown
Preascitic cirrhosis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12029629/	Palliative	Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ouabain-inhibiting activity of aldosterone antagonists.	1995 Jan	7792794
Endogenous and exogenous digoxin-like immunoreactive substances: impact on therapeutic drug monitoring of digoxin.	2002 Jul	12109847
Effect of canrenone on the digitalis site of Na+/K(+)-ATPase in human placental membranes and in erythrocytes.	2003 Jul	12827023
[Anti-angiogenic effects of aldosterone antagonists in the fibrin chamber in rats].	2003 Jul-Aug	12945230
Nanosuspension formulations for low-soluble drugs: pharmacokinetic evaluation using spironolactone as model compound.	2005 Mar	15830727
The Met852 residue is a key organizer of the ligand-binding cavity of the human mineralocorticoid receptor.	2005 May	15716462
Nongenomic effects of mineralocorticoid receptor activation in the cardiovascular system.	2005 May-Jun	15862816
Sodium pump alpha2 subunits control myogenic tone and blood pressure in mice.	2005 Nov 15	16166162
A new enzyme-linked chemiluminescent immunosorbent digoxin assay is virtually free from interference of spironolactone, potassium canrenoate, and their common metabolite canrenone.	2006	16960898
Simultaneous determination of spironolactone and its active metabolite canrenone in human plasma by HPLC-APCI-MS.	2006 Apr	16541392
Why are mineralocorticoid receptor antagonists cardioprotective?	2006 Dec	17075718
Effect of spironolactone on diuresis and urine sodium and potassium excretion in healthy dogs.	2007 Nov	18024236
Bioequivalence assessment of two formulations of spironolactone in Chinese healthy male volunteers.	2008	18488807
Effect of spironolactone, potassium canrenoate and their common metabolite canrenone on serum digoxin measurement by digoxin III, a new digoxin immunoassay.	2008 Dec	18824952
Immunohistochemical localization of transforming growth factor β-1 and its relationship with collagen expression in advanced liver fibrosis due to biliary atresia.	2010	21694865
Effect of spironolactone, potassium canrenoate, and their common metabolite canrenone on Dimension Vista Digoxin Assay.	2010	21089173
Spironolactone and canrenone inhibit UGT2B7-catalyzed human liver and kidney microsomal aldosterone 18beta-glucuronidation: a potential drug interaction.	2010 Jul	20304966
A systematic review and economic evaluation of the clinical effectiveness and cost-effectiveness of aldosterone antagonists for postmyocardial infarction heart failure.	2010 May	20492762

Patents

Sample Use Guides

In Vivo Use Guide

In the majority of cases are sufficient 50-200 mg per day, divided into one or more daily doses. In severe cases this dosage resistant or can be raised to 300 mg or more, according to medical prescription.

Route of Administration: Oral

In Vitro Use Guide

Canrenone (in concentration range: 0-10000 nM) decreased [3H]-progesterone binding to isolated uterine cytosolic progesterone receptors. The inhibition was concentration-dependent. Canrenone (in concentration range: 0-25150 nM) did not alter [3H]-oestradiol binding to isolated uterine cytosolic oestrogen receptors. Canrenone inhibition of progesterone binding to isolated cytosolic receptors was strictly competitive: Kd (apparent dissociation constant for progesterone binding) was increased in a concentration-dependent manner by canrenone, whereas Bmax (maximal number of progesterone binding sites/mg cytosolic protein) was unaltered. There was marked cooperativity in progesterone binding at high canrenone and low progesterone concentrations. The implication is that canrenone alters the subunit interaction of the receptor protein. Kd for progesterone was 3.2 X 10(-9)M. Ki (the inhibition constant for canrenone with respect to progesterone binding) was 300 X 10(-9)M.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:14:19 GMT 2023` Edited by `admin` on `Fri Dec 15 15:14:19 GMT 2023`
Record UNII	78O20X9J0U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CANRENONE

Official Name

English

17-Hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid γ-lactone

Common Name

English

Canrenone [WHO-DD]

Common Name

English

canrenone [INN]

Common Name

English

NSC-261713

Code

English

CANRENONE [MART.]

Common Name

English

2R)-3,4-DIHYDRO-5H-SPIRO(ANDROST-4,6-DIENE-17,2-FURAN)-3,5-DIONE

Systematic Name

English

SPIRONOLACTONE RELATED COMPOUND A

Common Name

English

17.ALPHA.-(2-CARBOXYETHYL)-17.BETA.-HYDROXYANDROSTA-4,6-DIEN-3-ONE LACTONE

Common Name

English

SPIRONOLACTONE IMPURITY F [EP IMPURITY]

Common Name

English

CANRENONE [USAN]

Common Name

English

PREGNA-4,6-DIENE-21-CARBOXYLIC ACID, 17-HYDROXY-3-OXO-, .GAMMA.-LACTONE (17.ALPHA.)-

Common Name

English

CANRENONE [MI]

Common Name

English

SC-9376

Code

English

SPIRONOLACTONE METABOLITE M1

Common Name

English

SPIRONOLACTONE RELATED COMPOUND A [USP-RS]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C03DA03