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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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Phase III
656
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Prevention and abolition of ouabain-induced ventricular tachycardia by potassium canrenoate in dogs.
1972 Aug
The influence of aldosterone and anticonvulsant drugs on electroencephalographic and clinical disturbances induced by the spirolactone derivative, potassium canrenoate.
1975 Jan
Ouabain-inhibiting activity of aldosterone antagonists.
1995 Jan
Additional beneficial effects of canrenoate in patients with anterior myocardial infarction on ACE-inhibitor treatment. A pilot study.
2001 Feb
Mineralocorticoid receptor blockade by canrenoate increases both spontaneous and stimulated adrenal function in humans.
2001 Jul
Determination and characterization of diuretics in human urine by liquid chromatography coupled to pneumatically assisted electrospray ionization mass spectrometry.
2001 Jun
Collecting duct is a site of sodium retention in PAN nephrosis: a rationale for amiloride therapy.
2001 Mar
Bidirectional (positive/negative) interference of spironolactone, canrenone, and potassium canrenoate on serum digoxin measurement: elimination of interference by measuring free digoxin or using a chemiluminescent assay for digoxin.
2002
Are some progestins genotoxic liver carcinogens?
2002 Dec
DNA damage in tissues of rat treated with potassium canrenoate.
2002 Feb 28
Endogenous and exogenous digoxin-like immunoreactive substances: impact on therapeutic drug monitoring of digoxin.
2002 Jul
Spironolactone and its main metabolite, canrenoic acid, block human ether-a-go-go-related gene channels.
2003 Feb 18
The renin-angiotensin-aldosterone system in patients with depression compared to controls--a sleep endocrine study.
2003 Oct 29
Acute aldosterone antagonism improves cardiac vagal control in humans.
2004 Apr 7
Electropharmacological effects of a spironolactone derivative, potassium canrenoate, assessed in the halothane-anesthetized canine model.
2004 Dec
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
Elevated resting and exercise-induced cortisol levels after mineralocorticoid receptor blockade with canrenoate in healthy humans.
2004 Oct
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
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
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
Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) "probes" for human udp-glucuronosyltransferases.
2006 Mar
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
Aldosterone induces CTGF in mesangial cells by activation of the glucocorticoid receptor.
2007 Nov
Corticosteroids mediate fast feedback of the rat hypothalamic-pituitary-adrenal axis via the mineralocorticoid receptor.
2008 Jun
Aldosterone blockade and left ventricular dysfunction: a systematic review of randomized clinical trials.
2009 Feb
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
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
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

Patents

US2011257140
3
US2014322323
3

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
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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
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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
Structure of CANRENOIC ACID
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CANRENOIC ACID
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