Clinical data | |
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Other names | 7α-TP4; SC-8365; 7α-Mercaptopregn-4-ene-3,20-dione |
Identifiers | |
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Chemical and physical data | |
Formula | C21H28O2S |
Molar mass | 344.51 g·mol−1 |
3D model ( JSmol) | |
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7α-Thioprogesterone (7α-TP4; developmental code name SC-8365; also known as 7α-mercaptopregn-4-ene-3,20-dione) is a synthetic, steroidal, and potent antimineralocorticoid (putative) and antiandrogen 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. [1] [2] [3] It is a derivative of progesterone (pregn-4-ene-3,20-dione) with a thio ( sulfur) substitution at the C7α position, and is related to the spirolactone group of drugs but lacks a γ- lactone ring. [1] [2]
As an antiandrogen, 7α-TP4 has approximately 8.5% of the affinity of dihydrotestosterone (DHT) for the rat ventral prostate androgen receptor (AR), which is similar to that of spironolactone and its active metabolite 7α-thiomethylspironolactone. [1] The drug has also been assessed at steroid hormone-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. [2]
7α-Acetylthio-17α-hydroxyprogesterone, a related derivative of progesterone and also of 17α-hydroxyprogesterone, has been found to possess potent antimineralocorticoid activity similarly. [4] Spironolactone is the derivative of this compound in which the acetyl group at the C17β position has been cyclized with the C17α hydroxyl group to form a spiro 21- carboxylic acid γ- lactone ring. [5] [6] [7]