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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H29O4.K
Molecular Weight 396.5616
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CANRENOATE POTASSIUM

SMILES

[K+].[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=JTZQCHFUGHIPDF-RYVBEKKQSA-M
InChI=1S/C22H30O4.K/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);/q;+1/p-1/t16-,17+,18+,20+,21+,22-;/m1./s1

HIDE SMILES / InChI

Molecular Formula K
Molecular Weight 39.0983
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H29O4
Molecular Weight 357.4633
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Prevention and abolition of ouabain-induced ventricular tachycardia by potassium canrenoate in dogs.
1972 Aug
Ouabain-inhibiting activity of aldosterone antagonists.
1995 Jan
Electropharmacological effects of a spironolactone derivative, potassium canrenoate, assessed in the halothane-anesthetized canine model.
2004 Dec
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
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
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
Inhibition of catecholamine-induced cardiac fibrosis by an aldosterone antagonist.
2005 Jan
Idiopathic primary hyperaldosteronism: normalization of plasma aldosterone after one month withdrawal of long-term therapy with aldosterone-receptor antagonist potassium canrenoate.
2005 Mar
Angiotensin II, angiotensin II antagonists and spironolactone and their modulation of cardiac repolarization.
2005 Mar
Aldosterone blunts human baroreflex sensitivity by a nongenomic mechanism.
2005 May
Nongenomic effects of mineralocorticoid receptor activation in the cardiovascular system.
2005 May-Jun
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
Hypothalamus-pituitary-adrenal hyperactivity in human aging is partially refractory to stimulation by mineralocorticoid receptor blockade.
2005 Oct
Prevention of renal impairment by continuous infusion of human atrial natriuretic peptide after liver transplantation.
2005 Oct 27
Spironolactone and its main metabolite canrenoic acid block hKv1.5, Kv4.3 and Kv7.1 + minK channels.
2005 Sep
Therapeutic drug monitoring of digoxin: impact of endogenous and exogenous digoxin-like immunoreactive substances.
2006
A new enzyme-linked chemiluminescent immunosorbent digoxin assay is virtually free from interference of spironolactone, potassium canrenoate, and their common metabolite canrenone.
2006
Why are mineralocorticoid receptor antagonists cardioprotective?
2006 Dec
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
Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) "probes" for human udp-glucuronosyltransferases.
2006 Mar
Effect of potassium canrenoate, an anti-aldosterone agent, on incidence of ascites and variceal progression in cirrhosis.
2006 Nov
A direct effect of aldosterone on endothelin-1 gene expression in vivo.
2007 Apr
Effects of spironolactone on glucose transport and interleukin-6 secretion in adipose cells of women.
2007 Dec
Modulating the development of renal tubules growing in serum-free culture medium at an artificial interstitium.
2007 Feb
Primary hyperaldosteronism is associated with derangement in the regulation of the hypothalamus-pituitary-adrenal axis in humans.
2007 Jul-Aug
Cirrhotic cardiomyopathy.
2007 Mar 27
Aldosterone induces CTGF in mesangial cells by activation of the glucocorticoid receptor.
2007 Nov
Spontaneous resolution of idiopathic aldosteronism after long-term treatment with potassium canrenoate.
2007 Oct
Time-course reduction of renal function in rats on high sodium intake: acute reversal by potassium canrenoate.
2008 Apr
Effect of spironolactone, potassium canrenoate and their common metabolite canrenone on serum digoxin measurement by digoxin III, a new digoxin immunoassay.
2008 Dec
Fadrozole reverses cardiac fibrosis in spontaneously hypertensive heart failure rats: discordant enantioselectivity versus reduction of plasma aldosterone.
2008 Jan
Corticosteroids mediate fast feedback of the rat hypothalamic-pituitary-adrenal axis via the mineralocorticoid receptor.
2008 Jun
Responses to diuretic treatment in gene-targeted mice lacking serum- and glucocorticoid-inducible kinase 1.
2009
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
Aldosterone blockade and left ventricular dysfunction: a systematic review of randomized clinical trials.
2009 Feb
Pharmacological characterization of intracellular, membrane, and plasma binding sites for corticosterone in house sparrows.
2009 Sep 1
Effect of spironolactone, potassium canrenoate, and their common metabolite canrenone on Dimension Vista Digoxin Assay.
2010
Clinical repercussions of analytical interferences due to aldosterone antagonists in digoxin immunoassays: an assessment.
2010 Apr
Combined versus sequential diuretic treatment of ascites in non-azotaemic patients with cirrhosis: results of an open randomised clinical trial.
2010 Jan
Predictors of large volume paracantesis induced circulatory dysfunction in patients with massive hepatic ascites.
2010 Jul
Spironolactone and canrenone inhibit UGT2B7-catalyzed human liver and kidney microsomal aldosterone 18beta-glucuronidation: a potential drug interaction.
2010 Jul
The endothelial mineralocorticoid receptor regulates vasoconstrictor tone and blood pressure.
2010 Jul
Cardioprotective effects of mineralocorticoid receptor antagonists at reperfusion.
2010 Jul
Amiloride reduces portal hypertension in rat liver cirrhosis.
2010 Jun
Effect of acute and prolonged mineralocorticoid receptor blockade on spontaneous and stimulated hypothalamic-pituitary-adrenal axis in humans.
2010 Jun
Cell and drug delivery therapeutics for controlled renal parenchyma regeneration.
2010 Jun 15
A systematic review and economic evaluation of the clinical effectiveness and cost-effectiveness of aldosterone antagonists for postmyocardial infarction heart failure.
2010 May
Steroidogenesis vs. steroid uptake in the heart: do corticosteroids mediate effects via cardiac mineralocorticoid receptors?
2010 May
Rationale for an early aldosterone blockade in acute myocardial infarction and design of the ALBATROSS trial.
2010 Oct
Heterogeneous nuclear ribonucleoprotein A2/B1 is a tissue-specific aldosterone target gene with prominent induction in the rat distal colon.
2013 Jan 15
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 18:48:38 GMT 2023
Edited
by admin
on Fri Dec 15 18:48:38 GMT 2023
Record UNII
M671F9NLEA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CANRENOATE POTASSIUM
USAN  
USAN  
Official Name English
CANRENONE FREE ACID POTASSIUM SALT [MI]
Common Name English
NSC-757789
Code English
CANRENOATE POTASSIUM [USAN]
Common Name English
KANRENOL
Brand Name English
POTASSIUM CANRENOATE [MART.]
Common Name English
POTASSIUM CANRENOATE [JAN]
Common Name English
POTASSIUM CANRENOATE
INN   MART.   WHO-DD  
INN  
Official Name English
SOLDACTONE
Brand Name English
PREGNA-4,6-DIENE-21-CARBOXYLIC ACID, 17-HYDROXY-3-OXO-, MONOPOTASSIUM SALT (17.ALPHA.)-
Common Name English
CANRENONE FREE ACID POTASSIUM SALT
MI  
Common Name English
potassium canrenoate [INN]
Common Name English
Potassium 17-hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylate
Common Name English
Potassium canrenoate [WHO-DD]
Common Name English
SC-14266
Code English
Classification Tree Code System Code
NCI_THESAURUS C547
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
WHO-VATC QC03DA02
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
WHO-ATC C03DA02
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
Code System Code Type Description
RXCUI
1981
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1616951
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
DRUG BANK
DB09015
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
NCI_THESAURUS
C81161
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
FDA UNII
M671F9NLEA
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
INN
2448
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
218-554-9
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PRIMARY
NSC
757789
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
MESH
D002191
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID2045602
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PRIMARY
PUBCHEM
23671691
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
WIKIPEDIA
POTASSIUM CANRENOATE
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
DRUG CENTRAL
477
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
SMS_ID
100000091863
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
CAS
2181-04-6
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
MERCK INDEX
m3023
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY Merck Index
EVMPD
SUB09983MIG
Created by admin on Fri Dec 15 18:48:38 GMT 2023 , Edited by admin on Fri Dec 15 18:48:38 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY