Canrenoate potassium | CAS#2181-04-6 |

MedKoo Cat#: 592498 | Name: Canrenoate potassium

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Canrenoate potassium is a synthetic pregnadiene derivative with anti-aldosterone activity.

Chemical Structure

Canrenoate potassium

CAS#2181-04-6

Theoretical Analysis

MedKoo Cat#: 592498

Name: Canrenoate potassium

CAS#: 2181-04-6

Chemical Formula: C22H29KO4

Exact Mass: 0.0000

Molecular Weight: 396.56

Elemental Analysis: C, 66.63; H, 7.37; K, 9.86; O, 16.14

Price and Availability

Size	Price	Availability	Quantity
1g	USD 250.00	2 Weeks
5g	USD 550.00	2 Weeks

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Synonym

Canrenoate potassium; Potassium Canrenoate; Canrenoic Acid Potassium Salt

IUPAC/Chemical Name

Potassium 17-Hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylate

InChi Key

JTZQCHFUGHIPDF-HUOQUVLESA-M

InChi Code

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

SMILES Code

C[C@@]12[C@](CCC([O-])=O)(O)CC[C@@]1([H])[C@]3([H])C=CC4=CC(CC[C@]4(C)[C@@]3([H])CC2)=O.[K+]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Canrenoate (Aldadiene) potassium, a prodrug that releases canrenone, is a potent, competitive mineralocorticoid receptor (aldosterone receptor) antagonist.

In vitro activity:

Potassium canrenoate (PC), a competitive aldosterone antagonist used as a diuretic and in the treatment of hypertension, was examined for its capacity to produce genotoxic effects in cultured rat and human cells. At subtoxic concentrations (10-90 microM) PC was found to induce a dose-dependent degree of DNA fragmentation, as detected by the Comet assay, and of DNA repair synthesis, as measured by quantitative autoradiography, in primary cultures of hepatocytes from rat and human donors of both genders. In rat hepatocytes both DNA fragmentation and DNA repair were more marked after 3 h than after 20 h exposure and in cultures from females than from males. In human hepatocytes from one male and two female donors, PC caused a similar effect in terms of DNA fragmentation, whereas DNA repair was detected in cultures from only two of the same three donors and was less marked than in rat hepatocytes. A modest but statistically significant increase in micronucleated cells was present in primary cultures of replicating rat hepatocytes exposed to 10 or 30 microM PC for 48 h, the response being, in this case also, more evident in females than in males. In contrast, PC did not induce micronucleus formation in human hepatocytes from two female donors. Any evidence of DNA fragmentation and micronucleus formation was absent in cultured human lymphocytes. Taken as a whole these findings support the hypothesis that hepatocytes activate PC to DNA-damaging reactive species. PC induced the observed genotoxic effects at concentrations close to those produced in humans by the administration of therapeutic doses, but these effects were as a whole more marked in rat than in human hepatocytes. Since PC shares the 17-hydroxy-3-oxopregna-4,6-diene structure with cyproterone acetate, chlormadinone acetate and megestrol acetate, previously found to be genotoxic to both rat and human hepatocytes, the potential carcinogenic hazard of this type of steroids cannot be neglected. Reference: Mutagenesis. 1999 Sep;14(5):463-72. https://academic.oup.com/mutage/article-lookup/doi/10.1093/mutage/14.5.463

In vivo activity:

The HFD significantly increased final body weight compared to the CTL group. The treatment with canrenoate potassium (PC) alone or in combination with AGIQ significantly decreased final body weight compared to the HFD group (Table 1). Food and water intake significantly decreased with the HFD feeding, independent of treatment with PC with or without AGIQ. Water intake versus the HFD group also significantly decreased with the treatment with PC with or without AGIQ. The HFD with or without PC alone or in combination with AGIQ significantly increased absolute and relative adipose tissue weights, and significantly decreased absolute and relative liver and kidney weights, when compared to the CTL group. In the HFD+PC group, the relative kidney weight significantly decreased compared to the CTL group but increased compared to the HFD group. Reference: J Toxicol Sci. 2018;43(10):611-621. https://dx.doi.org/10.2131/jts.43.611

	Solvent	mg/mL	mM
Solubility
	Water	100.0	252.17

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 396.56 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

In vitro protocol:

1. Martelli A, Mattioli F, Carrozzino R, Ferraris E, Marchese M, Angiola M, Brambilla G. Genotoxicity testing of potassium canrenoate in cultured rat and human cells. Mutagenesis. 1999 Sep;14(5):463-72. doi: 10.1093/mutage/14.5.463. PMID: 10473649. 2. Cook CS, Hauswald C, Oppermann JA, Schoenhard GL. Involvement of cytochrome P-450IIIA in metabolism of potassium canrenoate to an epoxide: mechanism of inhibition of the epoxide formation by spironolactone and its sulfur-containing metabolite. J Pharmacol Exp Ther. 1993 Jul;266(1):1-7. PMID: 8331551.

In vivo protocol:

1. Bos R, Mougenot N, Médiani O, Vanhoutte PM, Lechat P. Potassium canrenoate, an aldosterone receptor antagonist, reduces isoprenaline-induced cardiac fibrosis in the rat. J Pharmacol Exp Ther. 2004 Jun;309(3):1160-6. doi: 10.1124/jpet.103.063388. Epub 2004 Feb 5. PMID: 14764658. 2. Nakamura M, Eguchi A, Inohana M, Nagahara R, Murayama H, Kawashima M, Mizukami S, Koyanagi M, Hayashi SM, Maronpot RR, Shibutani M, Yoshida T. Differential impacts of mineralocorticoid receptor antagonist potassium canrenoate on liver and renal changes in high fat diet-mediated early hepatocarcinogenesis model rats. J Toxicol Sci. 2018;43(10):611-621. doi: 10.2131/jts.43.611. PMID: 30298849.

1: Koda M, Murawaki Y, Kawasaki H, Ikawa S. Effects of canrenoate potassium, an aldosterone antagonist on portal hemodynamics in patients with compensated liver cirrhosis. Hepatogastroenterology. 1996 Jul-Aug;43(10):887-92. PubMed PMID: 8884309. 2: Costa FV, Borghi C, Mussi A, Ambrosioni E. [Antihypertensive efficacy and effects on intra and extracellular electrolytes of a canrenoate potassium-butizide combination]. Minerva Cardioangiol. 1988 Oct;36(10):503-7. Italian. PubMed PMID: 3226562. 3: Niutta E, Cusi D, Colombo R, Tripodi G, Pellizzoni M, Pati P, Cesana B, Alberghini E, Barlassina C, Bianchi G. Antihypertensive effect of captopril, canrenoate potassium, and atenolol. Relations with red blood cell sodium transport and renin. Am J Hypertens. 1988 Oct;1(4 Pt 1):364-71. PubMed PMID: 3063286. 4: Nardoni A, di Piazza V, Moretti V, Copetti R, Trinco G, Geatti O. [False values of blood digoxin in patients with acute and chronic liver disease. Role of canrenoate potassium and comparison of radioimmunologic and immunoenzymatic methods]. Clin Ter. 1988 May 31;125(4):287-90. Italian. PubMed PMID: 2974364. 5: Traina M, Vizzini GB. [Controlled study of the effect of long-term administration of canrenoate potassium in cirrhotic ascites]. Minerva Med. 1986 Jan 28;77(3-4):87-91. Italian. PubMed PMID: 3511409. 6: Caporicci D, Achilli L. [Efficacy of canrenoate potassium in hypertensive cardiopathy. Clinical and echocardiographic evaluation]. Minerva Cardioangiol. 1984 Sep;32(9):581-7. Italian. PubMed PMID: 6514202. 7: Sarti F, Milandri GL, Piemontese A, Macchia S, Simoni S, Dal Monte PR. [Use of canrenoate potassium given orally in ascitogenic cirrhosis]. Minerva Dietol Gastroenterol. 1984 Jul-Sep;30(3):273-80. Italian. PubMed PMID: 6504377. 8: Matsuda K, Tatsuta N, Konishi Y, Minami K, Nishiwaki N, Yamasato A, Chiba Y, Ishihara H, Murata S, Shiraishi Y, Muraguchi T, Hikasa Y. [Therapeutic effect of canrenoate potassium (soldactone) in patients after open-heart surgery]. Nihon Geka Hokan. 1982 May 1;51(3):519-27. Japanese. PubMed PMID: 7138201. 9: Sidorenko BA, Kudisov IuM, Rossel's AN, Razumova ET. [Use of the aldosterone antagonist, canrenoate potassium for treating chronic circulatory insufficiency]. Kardiologiia. 1979 Mar;19(3):41-6. Russian. PubMed PMID: 372667. 10: Piepenbrock S, Hempelmann G, Volkholz E, Oelert H. [Cardiac and selective vascular effects of canrenoate-potassium (aldactone pro injectione) in cardiosurgical patients (author's transl)]. Prakt Anaesth. 1977 Oct;12(5):400-12. German. PubMed PMID: 917981. 11: Finn AM, Brown R, Sadée W. Tissue distribution of 3H-canrenoate potassium in rabbits. J Pharm Sci. 1977 Feb;66(2):275-7. PubMed PMID: 839430. 12: Finn AM, Finn C, Sadée W. Chemical structure and aldosterone receptor affinity of canrenoate-potassium metabolites in rabbits. Res Commun Chem Pathol Pharmacol. 1976 Dec;15(4):613-25. PubMed PMID: 1005910. 13: Eschner J, Fodor L, Ahnefeld FW. [Effect of canrenoate potassium on intraoperative disturbances of electrolyte equilibrium]. Infusionsther Klin Ernahr. 1976 Apr;3(2):98-104. German. PubMed PMID: 965083. 14: Consolo F, Ferraù O, Pitrone F, Luzza G, Russo A, Virga T. [Interference of canrenoate potassium with plasma renin activity. Note I. Effects of canrenoate potassiumon plasma renin activity in patients with essential hypertension]. Boll Soc Ital Biol Sper. 1975 Dec 30;51(24):1943-9. Italian. PubMed PMID: 1231877. 15: Kötter V, Leitner Ev, Arbeiter G, Cordes R, Schröder R. [Influence of canrenoate potassium (aldactone pro injections) on hemodynamics and myocardial ischemia in experimental myocardial infarct]. Z Kardiol. 1975 Jul;64(7):672-86. German. PubMed PMID: 1163092. 16: Gasperi A, Domenichini E, Ruozi P, Bobbio-Pallavicini F. [Canrenoate potassium in the treatment of hyperosmolar syndromes during resuscitation]. Minerva Anestesiol. 1974 Sep;40(9):448-54. Italian. PubMed PMID: 4423734. 17: Sadée W, Abshagen U, Finn C, Rietbrock N. Conversion of spironolactone to canrenone and disposition kinetics of spironolactone and canrenoate-potassium in rats. Naunyn Schmiedebergs Arch Pharmacol. 1974;283(3):303-18. PubMed PMID: 4276758. 18: Sadée W, Schröder R, von Leitner E, Dagcioglu M. Multiple dose kinetics of spironolactone and canrenoate-potassium in cardiac and hepatic failure. Eur J Clin Pharmacol. 1974;7(3):195-200. PubMed PMID: 4853286. 19: Dymling JF, Nilsson KO, Hökfelt B. The effect of Soldactona (canrenoate-potassium) on plasma testosterone and androstenedione and urinary 17-ketosteroids and 17-hydroxycorticosteroids. Acta Endocrinol (Copenh). 1972 May;70(1):104-12. PubMed PMID: 5067696.