Spirolactones
Spirolactones are a class of functional group in organic chemistry featuring a cyclic ester attached Spiro compound, 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 receptor antagonist, 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 spir ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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Drospirenone
Drospirenone is a progestin and antiandrogen medication which is used in birth control pills to prevent pregnancy and in menopausal hormone therapy, among other uses. It is available both alone under the brand name Slynd and in combination with an estrogen under the brand name Yasmin among others. The medication Is an analog of the drug spironolactone. Drospirenone is taken by mouth. Common side effects include acne, headache, breast tenderness, weight increase, and menstrual changes. Rare side effects may include high potassium levels and blood clots, among others. Drospirenone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has additional antimineralocorticoid and antiandrogenic activity and no other important hormonal activity. Because of its antimineralocorticoid activity and lack of undesirable off-target activity, drospirenone is said to more closely rese ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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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. It is also an important active metabolite of spironolactone, and partially accounts for its therapeutic effects. Medical uses Canrenone is mainly used as a diuretic. Canrenone has been found to be effective in the treatment of hirsutism in women. Heart failure Two studies of canrenone in people with heart failure have shown a mortality benefit compared to placebo. In the evaluation which studied people with chronic heart failure (CHF), people that were treated with canrenone displayed a lower number of deaths compared to the placebo group, indicating a death and morbidity benefit of the medication. One study compared 166 treated with canrenone to 336 given conventional therapy lasting 10 years. Differences in systolic and diastolic b ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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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]   |
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Spironolactone
Spironolactone, sold under the brand name Aldactone among others, is a medication that is primarily used to treat fluid build-up due to heart failure, liver scarring, or kidney disease. It is also used in the treatment of high blood pressure, low blood potassium that does not improve with supplementation, early puberty in boys, acne and excessive hair growth in women, and as a part of transgender hormone therapy in transfeminine people. Spironolactone is taken by mouth. Common side effects include electrolyte abnormalities, particularly high blood potassium, nausea, vomiting, headache, rashes, and a decreased desire for sex. In those with liver or kidney problems, extra care should be taken. Spironolactone has not been well studied in pregnancy and should not be used to treat high blood pressure of pregnancy. It is a steroid that blocks the effects of the hormones aldosterone and testosterone and has some estrogen-like effects. Spironolactone belongs to a cla ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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SC-5233
SC-5233, also known as 6,7-dihydrocanrenone or 20-spirox-4-ene-3,20-dione, is a synthetic, steroidal antimineralocorticoid of the spirolactone group which was developed by G. D. Searle & Company in the 1950s but was never marketed. It was the first synthetic antagonist of the mineralocorticoid receptor to have been identified and tested in humans. The drug was found to lack appreciable oral bioavailability and to be of low potency when administered parenterally, but it nonetheless produced a mild diuretic effect in patients with congestive heart failure. SC-8109, the 19-nor (19-demethyl) analogue, was developed and found to have improved oral bioavailability and potency, but still had low potency. Spironolactone (SC-9420; Aldactone) followed and had both good oral bioavailability and potency, and was the first synthetic antimineralocorticoid to be marketed. It has about 46-fold higher oral potency than SC-5233. SC-5233 is the propionic acid lactone of testosterone (androst-4-en ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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SC-8109
SC-8109 is a steroidal antimineralocorticoid of the spirolactone group which was never marketed. It is a potent antagonist of the mineralocorticoid receptor and is more potent than the related drug SC-5233 (of which SC-8109 is the 19-nor analogue). However, SC-8109 was found to have relatively low oral bioavailability and potency, though it nonetheless produced a mild diuretic effect in patients with congestive heart failure. Spironolactone (SC-9420; Aldactone), another spirolactone, followed and had both good oral bioavailability and potency, and was the first antimineralocorticoid to be marketed. In addition to its antimineralocorticoid activity, SC-8109 shows potent progestogenic activity, with similar potency relative to that of progesterone. Its analogue, SC-5233, possesses similar but less potent progestogenic activity. In addition, SC-5233 has been assessed and found to possess some antiandrogenic activity, antagonizing the effects of testosterone in animals, and SC-8109 ... [...More Info...]       [...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]   |
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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]   |
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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]   |
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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]   |
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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]   |
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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]   |
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Dicirenone
Dicirenone (International Nonproprietary Name, INN, United States Adopted Name, USAN; developmental code name SC-26304; also known as 7α-carboxyisopropylspirolactone) is a synthetic compound, synthetic, steroidal antimineralocorticoid of the spirolactone group which was developed as a diuretic and antihypertensive agent but was never marketed. It was chemical synthesis, synthesized and bioassay, assayed in 1974. Similarly to other spirolactones like spironolactone, dicirenone also possesses antiandrogen activity, albeit with relatively reduced affinity (pharmacology), affinity. 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]   |