Spirolactones are a class of functional group in

organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...

featuring a cyclic ester attached spiro to another ring system. The name is also used to refer to a class of synthetic

steroids A steroid is an organic compound with four fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter mem ...

, called steroid-17α-spirolactones, 17α-spirolactosteroids, or simply 17α-spirolactones, which feature their spirolactone group at the C17α position. They are antimineralocorticoids, or

antagonist An antagonist is a character in a story who is presented as the main enemy or rival of the protagonist and is often depicted as a villain.mineralocorticoid receptor The mineralocorticoid receptor (or MR, MLR, MCR), also known as the aldosterone receptor or nuclear receptor subfamily 3, group C, member 2, (NR3C2) is a protein that in humans is encoded by the ''NR3C2'' gene that is located on chromosome 4q31 ...

(which is activated predominantly by the

mineralocorticoid Mineralocorticoids are a class of corticosteroids, which in turn are a class of steroid hormones. Mineralocorticoids are produced in the adrenal cortex and influence salt and water balances (electrolyte balance and fluid balance). The primary ...

steroid hormone A steroid hormone is a steroid that acts as a hormone. Steroid hormones can be grouped into two classes: corticosteroids (typically made in the adrenal cortex, hence ''cortico-'') and sex steroids (typically made in the gonads or placenta). Wit ...

aldosterone Aldosterone is the main mineralocorticoid steroid hormone produced by the zona glomerulosa of the adrenal cortex in the adrenal gland. It is essential for sodium conservation in the kidney, salivary glands, sweat glands, and colon. It plays ...

), and have been employed clinically as potassium-sparing diuretics. Some also possess progestogenic and/or antiandrogen properties, which have both contributed to

side effect In medicine, a side effect is an effect of the use of a medicinal drug or other treatment, usually adverse but sometimes beneficial, that is unintended. Herbal and traditional medicines also have side effects. A drug or procedure usually use ...

s 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 include the marketed drugs spironolactone (SC-9420; Aldactone), canrenone (SC-9376; Cantaren, Luvion), potassium canrenoate (SC-14266; Venactone, Soldactone), eplerenone (SC-66110, CGP-30083; Inspra), and drospirenone (ZK-30595; Yasmin). Spirolactones that were not ever marketed include SC-5233, SC-8109, SC-11927 (Catatoxic Steroid 1; CS-1), spiroxasone, prorenone (SC-23133), prorenoate potassium (SC-23992), 7α-thiospironolactone (SC-24813), mexrenone (SC-25152, ZK-32055), dicirenone (SC-26304), 7α-thiomethylspironolactone (SC-26519), mexrenoate potassium (SC-26714), spirorenone (ZK-35973), ZK-91587 (15β,16β-methylenemexrenone), mespirenone (ZK-94679), and ZK-97894 (7α-thiomethylmespirenone). Oxprenoate potassium (RU-28318) is not a spirolactone by definition but is a closely related antimineralocorticoid that was never marketed. SC-5233 (6,7-dihydrocanrenone), the C17α propanoic acid lactone of

testosterone Testosterone is the primary male sex hormone and androgen in Male, males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testicles and prostate, as well as promoting se ...

(androst-4-en-17β-ol-3-one), is the unsubstituted

parent A parent is either the progenitor of a child or, in humans, it can refer to a caregiver or legal guardian, generally called an adoptive parent or step-parent. Parents who are progenitors are First-degree relative, first-degree relatives and have ...

or prototype compound of the spirolactones, and is one of a few of the simplest members of the series along with SC-8109 (the 19-demethyl analogue of SC-5233) and canrenone (the 1,2-didehydro analogue of SC-5233). Spironolactone is a derivative of SC-5233 with a 7α-acetylthio group (that is, SC-5233 is 7α-desthioacetylspironolactone).

References

Antimineralocorticoids Lactones Pregnanes Spiro compounds Spirolactones Spironolactone {{Steroid-stub

See also

References