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17α-Spirolactone
Spirolactones are a class of functional group in organic chemistry featuring a cyclic ester attached spiro to another ring system. The name is also used to refer to a class of synthetic steroids, called steroid-17α-spirolactones, 17α-spirolactosteroids, or simply 17α-spirolactones, which feature their spirolactone group at the C17α position. They are antimineralocorticoids, or antagonists of the mineralocorticoid receptor (which is activated predominantly by the mineralocorticoid steroid hormone aldosterone), and have been employed clinically as potassium-sparing diuretics. Some also possess progestogenic and/or antiandrogen properties, which have both contributed to side effects and been utilized for medical indications (e.g., spironolactone as an antiandrogen, and drospirenone as a progestin). The spirolactones were developed by G. D. Searle & Company in the 1950s and thereafter and were denoted as "SC" compounds (e.g., SC-9420 for spironolactone). The spirolactones inc ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Potassium-sparing Diuretics2
Potassium-sparing diuretics refers to drugs that cause diuresis without causing potassium loss in the urine. They are typically used as an adjunct in management of hypertension, cirrhosis, and congestive heart failure. The steroidal aldosterone antagonists can also be used for treatment of primary hyperaldosteronism. Spironolactone, a steroidal aldosterone antagonist, is also used in management of female hirsutism and acne from PCOS or other causes. Types of Potassium-Sparing Diuretics * Epithelial sodium channel blockers: ** Amiloride - better tolerated than triamterene ** Triamterene - increased renal side-effects * Aldosterone antagonists, also known as mineralocorticoid receptor antagonists: ** Spironolactone - most widespread use, inexpensive ** Eplerenone - more selective so reduced side-effects but more expensive and less potent ** Finerenone - non-steroidal, more selective and potent than spironolactone and eplerenone ** Canrenone - very limited use Mechanism of action ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Potassium Canrenoate
Potassium canrenoate ( INN, JAN) or canrenoate potassium (USAN) (brand names Venactone, Soldactone), also known as aldadiene kalium, the potassium salt of canrenoic acid, is an aldosterone antagonist of the spirolactone group. Like spironolactone, it is a prodrug, and is metabolized to active canrenone in the body. Potassium canrenoate is notable in that it is the only clinically used antimineralocorticoid which is available for parenteral administration (specifically intravenous) as opposed to oral administration. In the UK it is unlicensed and only used for short term diuresis in oedema or heart failure in neonates or children under specialist initiation and monitoring. See also * Canrenoic acid * Canrenone Canrenone, sold under the brand names Contaren, Luvion, Phanurane, and Spiroletan, is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone which is used as a diuretic in Europe, including in Italy and Belgium. ... References ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Spirorenone
Spirorenone (INN) (developmental code name ZK-35973) is a steroidal antimineralocorticoid of the spirolactone group that was never marketed. Spirorenone possesses 5–8 times the antimineralocorticoid activity of spironolactone in animal studies. The initial discovery of spirorenone was deemed a great success, as no compound with greater antimineralocorticoid activity had been developed since spironolactone in 1957. Moreover, spirorenone itself has virtually no affinity for the androgen receptor while its progestogenic activity shows species differences, being somewhat greater than that of spironolactone in rabbits but absent in mice and rats. As such, it was characterized as a highly potent antimineralocorticoid with far fewer hormonal side effects relative to spironolactone. In clinical trials, spirorenone was found to be 4- to 10-fold as potent as spironolactone as an antimineralocorticoid, and is said to be the most active antimineralocorticoid identified to date. However, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mexrenoate Potassium
Mexrenoate potassium (developmental code name SC-26714) is a synthetic steroidal antimineralocorticoid which was never marketed. See also * Mexrenoic acid * Mexrenone Mexrenone (code names ZK-32055, SC-25152) is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone that was never marketed. It is the lactonic form of mexrenoic acid (mexrenoate), and mexrenoate potassium (SC-2 ... References Abandoned drugs Antimineralocorticoids Carboxylic acids Enones Potassium compounds Pregnanes Spirolactones Tertiary alcohols {{steroid-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
7α-thiomethylspironolactone
7α-Thiomethylspironolactone (7α-TMS; developmental code name SC-26519) is a steroidal antimineralocorticoid and antiandrogen of the spirolactone group and the major active metabolite of spironolactone. Other important metabolites of spironolactone include 7α-thiospironolactone (7α-TS; SC-24813), 6β-hydroxy-7α-thiomethylspironolactone (6β-OH-7α-TMS), and canrenone (SC-9376). Spironolactone is a prodrug with a short terminal half-life of 1.4 hours. The active metabolites of spironolactone have extended terminal half-lives of 13.8 hours for 7α-TMS, 15.0 hours for 6β-OH-7α-TMS, and 16.5 hours for canrenone, and accordingly, these metabolites are responsible for the therapeutic effects of the drug. 7α-TS and 7α-TMS have been found to possess approximately equivalent affinity for the rat ventral prostate androgen receptor (AR) relative to that of spironolactone. The affinity of 7α-TS, 7α-TMS, and spironolactone for the rat prostate AR is about 3.0 to 8.5% of that o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dicirenone
Dicirenone (INN, USAN; developmental code name SC-26304; also known as 7α-carboxyisopropylspirolactone) is a synthetic, steroidal antimineralocorticoid of the spirolactone group which was developed as a diuretic and antihypertensive agent but was never marketed. It was synthesized and assayed in 1974. Similarly to other spirolactones like spironolactone, dicirenone also possesses antiandrogen activity, albeit with relatively reduced affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Par .... References Abandoned drugs Antimineralocorticoids Carboxylic acids Esters Isopropyl esters Lactones Pregnanes Spiro compounds Spirolactones Steroidal antiandrogens {{Cardiovascular-drug-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mexrenone
Mexrenone (code names ZK-32055, SC-25152) is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone that was never marketed. It is the lactonic form of mexrenoic acid (mexrenoate), and mexrenoate potassium (SC-26714), the potassium salt of mexrenoic acid, also exists. In addition to the mineralocorticoid receptor, mexrenone also binds to the glucocorticoid, androgen, and progesterone receptors. Relative to spironolactone, it has markedly reduced antiandrogen activity (approximately one-tenth of the antimineralocorticoid dosage equivalent antiandrogen activity of spironolactone). Eplerenone is the 9-11α- epoxy analogue of mexrenone. See also * Canrenone * Mexrenoate potassium * Mexrenoic acid * Potassium canrenoate * Prorenone Prorenone (developmental code name SC-23133) is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone that was never marketed. It is the lactonic form of prorenoic acid (prorenoate ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
7α-thiospironolactone
7α-Thiospironolactone (7α-TS; developmental code name SC-24813; also known as deacetylspironolactone) is a steroidal antimineralocorticoid and antiandrogen of the spirolactone group and a minor active metabolite of spironolactone. Other important metabolites of spironolactone include 7α-thiomethylspironolactone (7α-TMS; SC-26519), 6β-hydroxy-7α-thiomethylspironolactone (6β-OH-7α-TMS), and canrenone (SC-9376). Spironolactone is a prodrug with a short terminal half-life of 1.4 hours. The active metabolites of spironolactone have extended terminal half-lives of 13.8 hours for 7α-TMS, 15.0 hours for 6β-OH-7α-TMS, and 16.5 hours for canrenone, and accordingly, these metabolites are responsible for the therapeutic effects of the drug. 7α-TS and 7α-TMS have been found to possess approximately equivalent affinity for the rat ventral prostate androgen receptor (AR) relative to that of spironolactone. The affinity of 7α-TS, 7α-TMS, and spironolactone for the rat prost ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Prorenoate Potassium
Prorenoate potassium (developmental code name SC-23992) is a synthetic steroidal antimineralocorticoid An antimineralocorticoid, also known as a mineralocorticoid receptor antagonist (MRA or MCRA) or aldosterone antagonist, is a diuretic drug which antagonizes the action of aldosterone at mineralocorticoid receptors. This group of drugs is ofte ... which was never marketed. See also * Prorenoic acid * Prorenone References Abandoned drugs Antimineralocorticoids Carboxylic acids Ketones Potassium compounds Pregnanes Spirolactones Tertiary alcohols {{Steroid-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Prorenone
Prorenone (developmental code name SC-23133) is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone that was never marketed. It is the lactonic form of prorenoic acid (prorenoate), and prorenoate potassium (SC-23992), the potassium salt of prorenoic acid, also exists. Prorenoate potassium is about 8 times more potent than spironolactone as an antimineralocorticoid in animals, and it may act as a prodrug to prorenone. In addition to the mineralocorticoid receptor, prorenone also binds to the glucocorticoid, androgen, and progesterone receptors. The antiandrogenic potency of prorenone ''in vivo'' in animals is close to that of spironolactone. Similarly to spironolactone, prorenone is also a potent inhibitor of aldosterone biosynthesis. Chemistry Synthesis Prorenone can be synthesized via a Johnson–Corey–Chaykovsky reaction by reaction of canrenone with trimethylsulfonium iodide and sodium hydride Sodium hydride is the chemical compou ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Spiroxasone
Spiroxasone (, ) is a synthetic, steroidal antimineralocorticoid of the spirolactone group which was developed as a diuretic and antihypertensive agent but was never marketed. It was synthesized and assayed in 1963. The drug is 7α-acetylthiospirolactone with the ketone group removed from the C17α spirolactone ring. Similarly to other spirolactones like spironolactone, spiroxasone also possesses antiandrogen Antiandrogens, also known as androgen antagonists or testosterone blockers, are a class of drugs that prevent androgens like testosterone and dihydrotestosterone (DHT) from mediating their biological effects in the body. They act by blocking the ... activity. References Abandoned drugs Acetate esters Antimineralocorticoids Pregnanes Spiro compounds Spirolactones Steroidal antiandrogens Thioesters {{Cardiovascular-drug-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
