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

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

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 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Myocardial infarction 121 Sources: http://www.ncbi.nlm.nih.gov/pubmed/116612	Preventing		Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Prevention and abolition of ouabain-induced ventricular tachycardia by potassium canrenoate in dogs.	1972 Aug	5071786
Ouabain-inhibiting activity of aldosterone antagonists.	1995 Jan	7792794
Electropharmacological effects of a spironolactone derivative, potassium canrenoate, assessed in the halothane-anesthetized canine model.	2004 Dec	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 Nov 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 Oct	15791383
Screening procedure for detection of diuretics and uricosurics and/or their metabolites in human urine using gas chromatography-mass spectrometry after extractive methylation.	2005 Aug	16044110
Inhibition of catecholamine-induced cardiac fibrosis by an aldosterone antagonist.	2005 Jan	15613973
Idiopathic primary hyperaldosteronism: normalization of plasma aldosterone after one month withdrawal of long-term therapy with aldosterone-receptor antagonist potassium canrenoate.	2005 Mar	15952408
Angiotensin II, angiotensin II antagonists and spironolactone and their modulation of cardiac repolarization.	2005 Mar	15749161
Aldosterone blunts human baroreflex sensitivity by a nongenomic mechanism.	2005 May	15926109
Nongenomic effects of mineralocorticoid receptor activation in the cardiovascular system.	2005 May-Jun	15862816
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 Nov	16290961
Hypothalamus-pituitary-adrenal hyperactivity in human aging is partially refractory to stimulation by mineralocorticoid receptor blockade.	2005 Oct	16014406
Prevention of renal impairment by continuous infusion of human atrial natriuretic peptide after liver transplantation.	2005 Oct 27	16278591
Spironolactone and its main metabolite canrenoic acid block hKv1.5, Kv4.3 and Kv7.1 + minK channels.	2005 Sep	15980874
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
Why are mineralocorticoid receptor antagonists cardioprotective?	2006 Dec	17075718
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 Dec 1	17027009
Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) "probes" for human udp-glucuronosyltransferases.	2006 Mar	16381668
Effect of potassium canrenoate, an anti-aldosterone agent, on incidence of ascites and variceal progression in cirrhosis.	2006 Nov	16931172
A direct effect of aldosterone on endothelin-1 gene expression in vivo.	2007 Apr	17218419
Effects of spironolactone on glucose transport and interleukin-6 secretion in adipose cells of women.	2007 Dec	18075971
Modulating the development of renal tubules growing in serum-free culture medium at an artificial interstitium.	2007 Feb	17518563
Primary hyperaldosteronism is associated with derangement in the regulation of the hypothalamus-pituitary-adrenal axis in humans.	2007 Jul-Aug	17848838
Cirrhotic cardiomyopathy.	2007 Mar 27	17389039
Aldosterone induces CTGF in mesangial cells by activation of the glucocorticoid receptor.	2007 Nov	17602195
Spontaneous resolution of idiopathic aldosteronism after long-term treatment with potassium canrenoate.	2007 Oct	17709652
Time-course reduction of renal function in rats on high sodium intake: acute reversal by potassium canrenoate.	2008 Apr	18307731
Effect of spironolactone, potassium canrenoate and their common metabolite canrenone on serum digoxin measurement by digoxin III, a new digoxin immunoassay.	2008 Dec	18824952
Fadrozole reverses cardiac fibrosis in spontaneously hypertensive heart failure rats: discordant enantioselectivity versus reduction of plasma aldosterone.	2008 Jan	17884944
Corticosteroids mediate fast feedback of the rat hypothalamic-pituitary-adrenal axis via the mineralocorticoid receptor.	2008 Jun	18349112
Responses to diuretic treatment in gene-targeted mice lacking serum- and glucocorticoid-inducible kinase 1.	2009	19401625
Graz Endocrine Causes of Hypertension (GECOH) study: a diagnostic accuracy study of aldosterone to active renin ratio in screening for primary aldosteronism.	2009 Apr 7	19351411
Aldosterone blockade and left ventricular dysfunction: a systematic review of randomized clinical trials.	2009 Feb	19066207
Pharmacological characterization of intracellular, membrane, and plasma binding sites for corticosterone in house sparrows.	2009 Sep 1	19236873
Effect of spironolactone, potassium canrenoate, and their common metabolite canrenone on Dimension Vista Digoxin Assay.	2010	21089173
Clinical repercussions of analytical interferences due to aldosterone antagonists in digoxin immunoassays: an assessment.	2010 Apr	20216123
Combined versus sequential diuretic treatment of ascites in non-azotaemic patients with cirrhosis: results of an open randomised clinical trial.	2010 Jan	19570764
Predictors of large volume paracantesis induced circulatory dysfunction in patients with massive hepatic ascites.	2010 Jul	21187868
Spironolactone and canrenone inhibit UGT2B7-catalyzed human liver and kidney microsomal aldosterone 18beta-glucuronidation: a potential drug interaction.	2010 Jul	20304966
The endothelial mineralocorticoid receptor regulates vasoconstrictor tone and blood pressure.	2010 Jul	20299606
Cardioprotective effects of mineralocorticoid receptor antagonists at reperfusion.	2010 Jul	20028693
Amiloride reduces portal hypertension in rat liver cirrhosis.	2010 Jun	20551467
Effect of acute and prolonged mineralocorticoid receptor blockade on spontaneous and stimulated hypothalamic-pituitary-adrenal axis in humans.	2010 Jun	20219855
Cell and drug delivery therapeutics for controlled renal parenchyma regeneration.	2010 Jun 15	20122975
A systematic review and economic evaluation of the clinical effectiveness and cost-effectiveness of aldosterone antagonists for postmyocardial infarction heart failure.	2010 May	20492762
Steroidogenesis vs. steroid uptake in the heart: do corticosteroids mediate effects via cardiac mineralocorticoid receptors?	2010 May	20179635
Rationale for an early aldosterone blockade in acute myocardial infarction and design of the ALBATROSS trial.	2010 Oct	20934557
Heterogeneous nuclear ribonucleoprotein A2/B1 is a tissue-specific aldosterone target gene with prominent induction in the rat distal colon.	2013 Jan 15	23139218

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 `Fri Dec 15 16:10:29 UTC 2023` Edited by `admin` on `Fri Dec 15 16:10:29 UTC 2023`
Record UNII	87UG89VA9K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CANRENOIC ACID

Official Name

English

Canrenoic acid [WHO-DD]

Common Name

English

CANRENOATE

Common Name

English

canrenoic acid [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C242