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| Clinical data | |
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| Other names | 7α-TP4; SC-8365; 7α-Mercaptopregn-4-ene-3,20-dione |
| Identifiers | |
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| CAS Number |
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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 nameSC-8365; also known as7α-mercaptopregn-4-ene-3,20-dione) is asynthetic,steroidal, andpotentantimineralocorticoid (putative) andantiandrogen which was developed byG. 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 aderivative ofprogesterone (pregn-4-ene-3,20-dione) with athio (sulfur)substitution at the C7α position, and is related to thespirolactone group of drugs but lacks a γ-lactonering.[1][2]
As an antiandrogen, 7α-TP4 has approximately 8.5% of theaffinity ofdihydrotestosterone (DHT) for the ratventral prostateandrogen receptor (AR), which is similar to that ofspironolactone and itsactive metabolite7α-thiomethylspironolactone.[1] The drug has also been assessed atsteroid hormone-associatedcarrier proteins, and shows very low binding tosex hormone-binding globulin (SHBG) but high affinity forcorticosteroid-binding globulin (CBG) approximately equal to that of progesterone.[2]
7α-Acetylthio-17α-hydroxyprogesterone, a related derivative of progesterone and also of17α-hydroxyprogesterone, has been found to possess potent antimineralocorticoid activity similarly.[4] Spironolactone is the derivative of this compound in which theacetyl group at the C17β position has beencyclized with the C17α hydroxyl group to form aspiro 21-carboxylic acid γ-lactonering.[5][6][7]
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