CANRENOIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H30O4
Molecular Weight	358.4712
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC[C@H]3[C@@H](C=CC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@]2(O)CCC(O)=O

InChI

InChIKey=PBKZPPIHUVSDNM-WNHSNXHDSA-N

InChI=1S/C22H30O4/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21,26)12-8-19(24)25/h3-4,13,16-18,26H,5-12H2,1-2H3,(H,24,25)/t16-,17+,18+,20+,21+,22-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H30O4
Molecular Weight	358.4712
Charge	0
Count

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

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/24423282
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/25389106

Potassium canrenoate (INN, JAN) or canrenoate potassium (USAN) (brand names Venactone, Soldactone), the potassium salt of canrenoic acid, is an aldosterone antagonist of the spirolactone group. Like spironolactone, it is a prodrug, which is metabolized to canrenone in the body. Potassium canrenoate is not licensed in the UK, but may sometimes be prescribed off-licence to treat oedema. It is given intravenously. Potassium canrenoate is a mineralocorticoid receptor (MR) antagonist. The blockade with MR antagonist have beneficial effects in patients with heart failure and myocardial infarction, often attributed to blocking aldosterone action in the myocardium.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mineralocorticoid receptor 53 Target ID: CHEMBL1994 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14171763	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Myocardial infarction 125 Sources: http://www.ncbi.nlm.nih.gov/pubmed/116612	Preventing		Phase III 665	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Heterogeneous nuclear ribonucleoprotein A2/B1 is a tissue-specific aldosterone target gene with prominent induction in the rat distal colon.	2013-01-15	23139218
Rationale for an early aldosterone blockade in acute myocardial infarction and design of the ALBATROSS trial.	2010-10	20934557
Predictors of large volume paracantesis induced circulatory dysfunction in patients with massive hepatic ascites.	2010-07	21187868
Spironolactone and canrenone inhibit UGT2B7-catalyzed human liver and kidney microsomal aldosterone 18beta-glucuronidation: a potential drug interaction.	2010-07	20304966
The endothelial mineralocorticoid receptor regulates vasoconstrictor tone and blood pressure.	2010-07	20299606
Cardioprotective effects of mineralocorticoid receptor antagonists at reperfusion.	2010-07	20028693
Cell and drug delivery therapeutics for controlled renal parenchyma regeneration.	2010-06-15	20122975
Amiloride reduces portal hypertension in rat liver cirrhosis.	2010-06	20551467
Effect of acute and prolonged mineralocorticoid receptor blockade on spontaneous and stimulated hypothalamic-pituitary-adrenal axis in humans.	2010-06	20219855
A systematic review and economic evaluation of the clinical effectiveness and cost-effectiveness of aldosterone antagonists for postmyocardial infarction heart failure.	2010-05	20492762
Steroidogenesis vs. steroid uptake in the heart: do corticosteroids mediate effects via cardiac mineralocorticoid receptors?	2010-05	20179635
Clinical repercussions of analytical interferences due to aldosterone antagonists in digoxin immunoassays: an assessment.	2010-04	20216123
Combined versus sequential diuretic treatment of ascites in non-azotaemic patients with cirrhosis: results of an open randomised clinical trial.	2010-01	19570764
Effect of spironolactone, potassium canrenoate, and their common metabolite canrenone on Dimension Vista Digoxin Assay.	2010	21089173
Pharmacological characterization of intracellular, membrane, and plasma binding sites for corticosterone in house sparrows.	2009-09-01	19236873
Graz Endocrine Causes of Hypertension (GECOH) study: a diagnostic accuracy study of aldosterone to active renin ratio in screening for primary aldosteronism.	2009-04-07	19351411
Aldosterone blockade and left ventricular dysfunction: a systematic review of randomized clinical trials.	2009-02	19066207
Responses to diuretic treatment in gene-targeted mice lacking serum- and glucocorticoid-inducible kinase 1.	2009	19401625
Effect of spironolactone, potassium canrenoate and their common metabolite canrenone on serum digoxin measurement by digoxin III, a new digoxin immunoassay.	2008-12	18824952
Corticosteroids mediate fast feedback of the rat hypothalamic-pituitary-adrenal axis via the mineralocorticoid receptor.	2008-06	18349112
Time-course reduction of renal function in rats on high sodium intake: acute reversal by potassium canrenoate.	2008-04	18307731
Fadrozole reverses cardiac fibrosis in spontaneously hypertensive heart failure rats: discordant enantioselectivity versus reduction of plasma aldosterone.	2008-01	17884944
Effects of spironolactone on glucose transport and interleukin-6 secretion in adipose cells of women.	2007-12	18075971
Aldosterone induces CTGF in mesangial cells by activation of the glucocorticoid receptor.	2007-11	17602195
Spontaneous resolution of idiopathic aldosteronism after long-term treatment with potassium canrenoate.	2007-10	17709652
Primary hyperaldosteronism is associated with derangement in the regulation of the hypothalamus-pituitary-adrenal axis in humans.	2007-09-13	17848838
A direct effect of aldosterone on endothelin-1 gene expression in vivo.	2007-04	17218419
Cirrhotic cardiomyopathy.	2007-03-27	17389039
Modulating the development of renal tubules growing in serum-free culture medium at an artificial interstitium.	2007-02	17518563
Fast gas chromatographic/mass spectrometric determination of diuretics and masking agents in human urine: Development and validation of a productive screening protocol for antidoping analysis.	2006-12-01	17027009
Why are mineralocorticoid receptor antagonists cardioprotective?	2006-12	17075718
Effect of potassium canrenoate, an anti-aldosterone agent, on incidence of ascites and variceal progression in cirrhosis.	2006-11	16931172
Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) "probes" for human udp-glucuronosyltransferases.	2006-03	16381668
Therapeutic drug monitoring of digoxin: impact of endogenous and exogenous digoxin-like immunoreactive substances.	2006	17288498
A new enzyme-linked chemiluminescent immunosorbent digoxin assay is virtually free from interference of spironolactone, potassium canrenoate, and their common metabolite canrenone.	2006	16960898
Effects of canrenoate plus angiotensin-converting enzyme inhibitors versus angiotensin-converting enzyme inhibitors alone on systolic and diastolic function in patients with acute anterior myocardial infarction.	2005-11	16290961
Prevention of renal impairment by continuous infusion of human atrial natriuretic peptide after liver transplantation.	2005-10-27	16278591
Hypothalamus-pituitary-adrenal hyperactivity in human aging is partially refractory to stimulation by mineralocorticoid receptor blockade.	2005-10	16014406
Spironolactone and its main metabolite canrenoic acid block hKv1.5, Kv4.3 and Kv7.1 + minK channels.	2005-09	15980874
Screening procedure for detection of diuretics and uricosurics and/or their metabolites in human urine using gas chromatography-mass spectrometry after extractive methylation.	2005-08	16044110
Nongenomic effects of mineralocorticoid receptor activation in the cardiovascular system.	2005-05-03	15862816
Aldosterone blunts human baroreflex sensitivity by a nongenomic mechanism.	2005-05	15926109
Idiopathic primary hyperaldosteronism: normalization of plasma aldosterone after one month withdrawal of long-term therapy with aldosterone-receptor antagonist potassium canrenoate.	2005-03	15952408
Angiotensin II, angiotensin II antagonists and spironolactone and their modulation of cardiac repolarization.	2005-03	15749161
Inhibition of catecholamine-induced cardiac fibrosis by an aldosterone antagonist.	2005-01	15613973
Electropharmacological effects of a spironolactone derivative, potassium canrenoate, assessed in the halothane-anesthetized canine model.	2004-12	15599107
DNA fragmentation, DNA repair and apoptosis induced in primary rat hepatocytes by dienogest, dydrogesterone and 1,4,6-androstatriene-17beta-ol-3-one acetate.	2004-11-14	15474407
Effects of the aldosterone receptor antagonist potassium canrenoate on renal blood flow and urinary output during prolonged increased intraabdominal pressure (IAP) in pigs.	2004-10	15791383
Ouabain-inhibiting activity of aldosterone antagonists.	1995-01	7792794
Prevention and abolition of ouabain-induced ventricular tachycardia by potassium canrenoate in dogs.	1972-08	5071786

Patents

Sample Use Guides

In Vivo Use Guide

400 mg of Potassium-Canrenoate

Route of Administration: Intravenous

In Vitro Use Guide

potassium canrenoate, in a concentration-dependent manner (3-30 uM), inhibited the increase in basal tone induced by receptorial (ouabain), most likely acting as antagonist for ouabain binding site on Na(+)-K+ATPase pump

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:20:54 GMT 2025` Edited by `admin` on `Mon Mar 31 18:20:54 GMT 2025`
Record UNII	87UG89VA9K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CANRENOIC ACID

Official Name

English

CANRENOATE

Preferred Name

English

Canrenoic acid [WHO-DD]

Common Name

English

canrenoic acid [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C242