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SML1497

Sigma-Aldrich

Canrenone

≥97% (HPLC)

Synonym(s):

(17α)-17-Hydroxy-3-oxopregna-4,6-diene-21-carboxylic acid γ-lactone, NSC 261713

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About This Item

Empirical Formula (Hill Notation):
C22H28O3
CAS Number:
976-71-6
Molecular Weight:
340.46
MDL number:
MFCD00071735
UNSPSC Code:
12352200
PubChem Substance ID:
329825921
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

optical activity

[α]/D +17 to +24°, c = 1 in chloroform-d

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

room temp

SMILES string

C[C@@]12C(C=C[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]45OC(CC5)=O)=CC(CC1)=O

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

InChI key

UJVLDDZCTMKXJK-WNHSNXHDSA-N

Gene Information

human ... NR3C2(4306)

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Biochem/physiol Actions

Canrenone is a mineralocorticoid (aldosterone) inhibitor.
Canrenone is a mineralocorticoid (aldosterone) inhibitor. Aldosterone is known to be involved in hypertension, kidney disease, atherosclerosis, and heart failure. Blockade of the aldosterone receptor has been shown to improve cardiovascular function. In congestive heart failure, aldosterone antagonists are used in addition to other drugs for additive diuretic effect, which reduces edema and the cardiac workload.
Canrenone is an active metabolite of spironolactone with potassium-sparing diuretic activity. Canrenone specifically antagonizes aldosterone at the mineralocorticoid receptor in the kidneys, thereby increasing sodium excretion and inhibiting potassium excretion. It is known to reduce the inflammatory reaction influenced by aldosterone.

Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Warning

Hazard Statements

H351,H411

Hazard Classifications

Aquatic Chronic 2 - Carc. 2 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Decio Armanini et al.
Expert opinion on pharmacotherapy, 15(7), 909-912 (2014-03-13)
Canrenone is a derivative of spironolactone with lower antiandrogen activity. The drug is used only in few countries and can block all the side effects of aldosterone (ALDO). The drug is effective even in the presence of normal concentrations of
Li-jun Hu et al.
British journal of clinical pharmacology, 75(5), 1202-1212 (2012-10-24)
Aldosterone antagonists (AldoAs) have been used to treat severe chronic heart failure (CHF). There is uncertainty regarding the efficacy of using AldoAs in mild to moderate CHF with New York Heart Association (NYHA) classifications of I to II. This study
Digoxin assays: frequent, substantial, and potentially dangerous interference by spironolactone, canrenone, and other steroids.
StEiMER W E R N E R, et al.
Clinical Chemistry, 48(3), 507-516 (2002)
Aldosterone receptor blockers spironolactone and canrenone: two multivalent drugs.
Armanini D, et al.
Expert Opinion on Pharmacotherapy, 15, 909-912 (2014)
Giuseppe Derosa et al.
Annals of medicine, 47(1), 47-52 (2014-10-17)
To evaluate the effects of canrenone compared to placebo on blood pressure control, some non-conventional biomarkers in cardiovascular stratification, and on metalloproteinases in patients affected by metabolic syndrome. A total of 156 Caucasian patients were treated with placebo or canrenone

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