Canrenon

Structural formula
General
Surname	Canrenon
other names	(17α) -17-Hydroxy-3-oxopregna-4,6-diene-21-carboxylic acid-γ-lactone; (2 ′ R ) -3 ′, 4′-dihydro-5 ′ H -spiro [androst-4,6-diene-17,2′-furan] -3,5′-dione; NSC 261713;
Molecular formula	C 22 H 28 O 3
Brief description	white to beige solid
External identifiers / databases
ECHA InfoCard	100.012.322
PubChem	13789
ChemSpider	13192
DrugBank	DB12221
Wikidata	Q5033475
Drug information
ATC code	C03 DA03
properties
Molar mass	340.46 g mol −1
Physical state	firmly
Melting point	149-151 ° C
solubility	soluble in DMSO (20 g l −1 at 20 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 351-411
	P: 280
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Canrenone is a chemical compound and a drug belonging to the group of aldosterone receptor antagonists .

It provides the γ- lactone form of Canrenoinsäure represents.

Extraction and presentation

Canrenone can be obtained by dehydrating 3-oxo-17α-hydroxy-pregna-4-en-21-carbolactone . A synthesis was first described in 1959.

properties

Canrenone is a white to yellow solid. It is a metabolite of spironolactone . Chemically, it is a synthetic derivative of a steroid hormone .

use

Canrenone itself is not used as a medicinal substance, but in the form of the sodium or potassium salt (potassium canrenoate) of canrenoic acid. Canrenone is formed metabolically after parenteral administration of potassium canrenoate and blocks the action of the adrenal cortex hormone aldosterone by binding to the aldosterone receptors. Aldosterone works in the kidney , where it inhibits the excretion of sodium and increases the excretion of potassium . By suppressing the aldosterone effect, Canrenon causes a reduction in blood volume and thus blood pressure through increased sodium and water excretion , without increasing potassium excretion ( potassium-sparing diuresis ). In therapeutic doses, Canrenon inhibits neither the biosynthesis nor the release of aldosterone.

Potassium Canrenoate

Potassium canrenoate is indicated for the treatment of primary aldosteronism and edema and ascites due to secondary aldosteronism (trade name: Aldactone canrenoate ). Potassium canrenoate is given intravenously. Because of the metabolic formation of carcinogenic epoxides , the use of potassium canrenoate has been significantly restricted.

doping

Use by competitive athletes is prohibited. Canrenon or potassium canrenoate is misused as a masking agent for doping substances.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f data sheet Canrenone, ≥97% (HPLC) from Sigma-Aldrich , accessed on March 28, 2020 ( PDF ).
↑ ^a ^b Datasheet Canrenone, 98% at AlfaAesar, accessed on March 27, 2020 ( PDF )(JavaScript required) .
↑ External identifiers or database links for canrenoic acid : CAS number: 4138-96-9, EC number: 223-963-0, ECHA InfoCard: 100.021.785 , PubChem : 656615 , ChemSpider : 570976 , DrugBank : DB09015 , Wikidata : Q39045292 .
↑ ^a ^b F.v. Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hager's handbook of pharmaceutical practice substances AD . Springer-Verlag, 2013, ISBN 978-3-642-57995-0 , pp. 654 ( limited preview in Google Book search).
↑ John A. Cella, Robert C. Tweit: Steroidal Aldosterone Blockers. II. In: The Journal of Organic Chemistry. 24, 1959, p. 1109, doi : 10.1021 / jo01090a019 .
↑ ^a ^b G. Geisslinger et al .: Mutschler drug effects . 11th edition. WVG, Stuttgart 2019, p. 610 f .
↑ Product information Aldactone® 10 ml canrenoate . Riemser Pharma GmbH. Status: December 2018.
↑ External identifiers or database links for potassium canrenoate: CAS number: 2181-04-6, EC number: 218-554-9, ECHA InfoCard: 100.016.868 , PubChem : 656614 , ChemSpider : 570975 , DrugBank : DB09015 , Wikidata : Q3655600 .
^ Georg Neumann: Nutrition in Sport . Meyer & Meyer Verlag, 2014, ISBN 978-3-89899-861-1 , p. 317 ( limited preview in Google Book search).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f data sheet Canrenone, ≥97% (HPLC) from Sigma-Aldrich , accessed on March 28, 2020 ( PDF ).

[Alfa-2] Datasheet Canrenone, 98% at AlfaAesar, accessed on March 27, 2020 ( PDF )(JavaScript required) .

[3] External identifiers or database links for canrenoic acid : CAS number: 4138-96-9, EC number: 223-963-0, ECHA InfoCard: 100.021.785 , PubChem : 656615 , ChemSpider : 570976 , DrugBank : DB09015 , Wikidata : Q39045292 .

[F.v._Bruchhausen,_S._Ebel,_A.W._Frahm,_E._Hackenthal-4] F.v. Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hager's handbook of pharmaceutical practice substances AD . Springer-Verlag, 2013, ISBN 978-3-642-57995-0 , pp. 654 ( limited preview in Google Book search).

[DOI10.1021/jo01090a019-5] John A. Cella, Robert C. Tweit: Steroidal Aldosterone Blockers. II. In: The Journal of Organic Chemistry. 24, 1959, p. 1109, doi : 10.1021 / jo01090a019 .

[mutsch-6] G. Geisslinger et al .: Mutschler drug effects . 11th edition. WVG, Stuttgart 2019, p. 610 f .

[7] Product information Aldactone® 10 ml canrenoate . Riemser Pharma GmbH. Status: December 2018.

[8] External identifiers or database links for potassium canrenoate: CAS number: 2181-04-6, EC number: 218-554-9, ECHA InfoCard: 100.016.868 , PubChem : 656614 , ChemSpider : 570975 , DrugBank : DB09015 , Wikidata : Q3655600 .

[Georg_Neumann-9] Georg Neumann: Nutrition in Sport . Meyer & Meyer Verlag, 2014, ISBN 978-3-89899-861-1 , p. 317 ( limited preview in Google Book search).