Prorenone (developmental code name SC-23133) is a
steroid
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...
al
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 often u ...
of the
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-spirol ...
group related to
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 ...
that was never marketed.
It is the
lactonic form of
prorenoic acid
Prorenoic acid, or prorenoate, is a synthetic steroidal antimineralocorticoid which was never marketed.
See also
* Prorenoate potassium
Prorenoate potassium (developmental code name SC-23992) is a synthetic steroidal antimineralocorticoid ...
(prorenoate), and
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 dru ...
(SC-23992), the
potassium
Potassium is the chemical element with the symbol K (from Neo-Latin ''kalium'') and atomic number19. Potassium is a silvery-white metal that is soft enough to be cut with a knife with little force. Potassium metal reacts rapidly with atmosphe ...
salt
Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quantitie ...
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
A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...
to prorenone.
In addition to the
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 ...
, prorenone also binds to the
glucocorticoid
Glucocorticoids (or, less commonly, glucocorticosteroids) are a class of corticosteroids, which are a class of steroid hormones. Glucocorticoids are corticosteroids that bind to the glucocorticoid receptor that is present in almost every vertebr ...
,
androgen
An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This inc ...
, and
progesterone receptor
The progesterone receptor (PR), also known as NR3C3 or nuclear receptor subfamily 3, group C, member 3, is a protein found inside cells. It is activated by the steroid hormone progesterone.
In humans, PR is encoded by a single ''PGR'' gene resid ...
s.
The antiandrogenic potency of prorenone ''
in vivo
Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, and ...
'' in animals is close to that of spironolactone.
Similarly to spironolactone, prorenone is also a potent
inhibitor
Inhibitor or inhibition may refer to:
In biology
* Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity
* Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotra ...
of
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 a c ...
biosynthesis
Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. ...
.
Chemistry
Synthesis
Prorenone can be synthesized via a
Johnson–Corey–Chaykovsky reaction
The Johnson–Corey–Chaykovsky reaction (sometimes referred to as the Corey–Chaykovsky reaction or CCR) is a chemical reaction used in organic chemistry for the synthesis of epoxides, aziridines, and cyclopropanes. It was discovered in 1961 ...
by reaction of canrenone with
trimethylsulfonium iodide
Trimethylsulfonium (systematically named trimethylsulfanium and trimethylsulfur(1+)) is an organic chemistry, organic cation with the chemical formula (CH3)3S+ (also written as ).
Compounds
Several salt (chemistry), salts of trimethylsulfonium ...
and
sodium hydride
Sodium hydride is the chemical compound with the empirical formula Na H. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H− ions, in co ...
.
[Chinn, L.; 1974, ]
:
See also
*
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 ...
*
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 ...
*
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 dru ...
*
Prorenoic acid
Prorenoic acid, or prorenoate, is a synthetic steroidal antimineralocorticoid which was never marketed.
See also
* Prorenoate potassium
Prorenoate potassium (developmental code name SC-23992) is a synthetic steroidal antimineralocorticoid ...
*
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 spironolact ...
References
Antiandrogens
Antimineralocorticoids
Cyclopropanes
Pregnanes
Progestogens
Spiro compounds
Spirolactones
Steroidal antiandrogens
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