7α-Thioprogesterone (7α-TP4; developmental code name SC-8365; also known as 7α-mercaptopregn-4-ene-3,20-dione) is a synthetic,

steroid A steroid is an organic compound with four fused compound, 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 t ...

al, and potent antimineralocorticoid (putative) and

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 t ...

which was developed by G. D. Searle & Co and was described in the late 1970s and early 1980s but was never developed or introduced for medical use. It is a

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

progesterone Progesterone (; P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the ma ...

(pregn-4-ene-3,20-dione) with a thio (

sulfur Sulfur ( American spelling and the preferred IUPAC name) or sulphur ( Commonwealth spelling) is a chemical element; it has symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms ...

) substitution at the C7α position, and is related to the spirolactone group of drugs but lacks a γ- lactone ring. As an antiandrogen, 7α-TP4 has approximately 8.5% of the

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 Pa ...

dihydrotestosterone Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production o ...

(DHT) for the rat ventral prostate

androgen receptor The androgen receptor (AR), also known as NR3C4 (nuclear receptor subfamily 3, group C, member 4), is a type of nuclear receptor that is activated by binding any of the androgenic hormones, including testosterone and dihydrotestosterone, in th ...

(AR), which is similar to that of

spironolactone Spironolactone, sold under the brand name Aldactone among others, is classed as a diuretic medication. It can be used to treat edema, fluid build-up due to hepatic cirrhosis, liver disease or kidney disease. It is also used to reduce risk o ...

and its active metabolite 7α-thiomethylspironolactone. The drug has also been assessed at

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 ...

-associated carrier proteins, and shows very low binding to sex hormone-binding globulin (SHBG) but high affinity for corticosteroid-binding globulin (CBG) approximately equal to that of progesterone. 7α-Acetylthio-17α-hydroxyprogesterone, a related derivative of progesterone and also of 17α-hydroxyprogesterone, has been found to possess potent antimineralocorticoid activity similarly. Spironolactone is the derivative of this compound in which the

acetyl group In organic chemistry, an acetyl group is a functional group denoted by the chemical formula and the structure . It is sometimes represented by the symbol Ac (not to be confused with the element actinium). In IUPAC nomenclature, an acetyl grou ...

at the C17β position has been cyclized with the C17α hydroxyl group to form a spiro 21-

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...

γ- lactone ring.

References

Antimineralocorticoids Diketones Organosulfur compounds Pregnanes Steroidal antiandrogens {{Genito-urinary-drug-stub