7α-Thioprogesterone

7α-Thioprogesterone
Identifiers
Synonyms 7α-TP4; SC-8365; 7α-Mercaptopregn-4-ene-3,20-dione
Chemical and physical data
Formula C21H28O2S
Molar mass 344.511 g/mol
3D model (JSmol)

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 the same affinity as that of spironolactone and its active metabolites like 7α-thiomethylspironolactone for the rat ventral prostate androgen receptor (AR), which is in the range of 3.0 to 8.5% of that of dihydrotestosterone (DHT).[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]

References

  1. 1 2 3 Cutler GB, Pita JC, Rifka SM, Menard RH, Sauer MA, Loriaux DL (1978). "SC 25152: A potent mineralocorticoid antagonist with reduced affinity for the 5 alpha-dihydrotestosterone receptor of human and rat prostate". J. Clin. Endocrinol. Metab. 47 (1): 171–5. PMID 263288. doi:10.1210/jcem-47-1-171.
  2. 1 2 3 Pugeat MM, Dunn JF, Nisula BC (1981). "Transport of steroid hormones: interaction of 70 drugs with testosterone-binding globulin and corticosteroid-binding globulin in human plasma". J. Clin. Endocrinol. Metab. 53 (1): 69–75. PMID 7195405. doi:10.1210/jcem-53-1-69.
  3. ↑ Ulrich Westphal (6 December 2012). Steroid-Protein Interactions II. Springer Science & Business Media. pp. 501–. ISBN 978-3-642-82486-9.



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