SC-5233
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| Clinical data | |
|---|---|
| Routes of administration | Oral |
| ATC code | None |
| Identifiers | |
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| Synonyms | 7-Desthioacetylspironolactone |
| CAS Number | 976-70-5 |
| PubChem (CID) | 101931 |
| ChemSpider | 92091 |
| ChEMBL | CHEMBL400534 |
| Chemical and physical data | |
| Formula | C22H30O3 |
| Molar mass | 342.4718 g/mol |
| 3D model (Jmol) | Interactive image |
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SC-5233, also known as 6,7-dihydrocanrenone or 20-spirox-4-ene-3,20-dione, is a steroidal antimineralocorticoid of the spirolactone group that was developed by G. D. Searle & Company in the 1950s but was never marketed.[1][2] It was the first antagonist of the mineralocorticoid receptor to have been identified and tested in humans.[1][3] The drug was found to have poor oral bioavailability and potency,[4] but it nonetheless produced a mild diuretic effect in patients with congestive heart failure.[1] SC-8109, the 19-nor (19-demethyl) analogue, was developed and found to have improved oral bioavailability and potency, but still had relatively low potency.[5] Spironolactone (SC-9420; Aldactone) followed and had both good oral bioavailability and potency, and was the first antimineralocorticoid to be marketed.[3]
SC-5233 is the propionic acid lactone of 17β-hydroxyandrost-4-en-3-one or testosterone and is also known 3-(3-oxo-17β-hydroxyandrost-4-en-17α-yl)propionic acid γ-lactone or as 17α-(2-carboxyethyl)testosterone γ-lactone.[6] It is the unsubstituted parent or prototype compound of the spirolactone family of steroidal antimineralocorticoids.[2][7]
Similarly to other spirolactones like canrenone and spironolactone, SC-5233 has antiandrogen activity and antagonizes the effects of testosterone in animals.[6] In addition, along with SC-8109, it has been found to possess potent progestogenic activity.[8]
References
- 1 2 3 E. Buchborn; K. D. Bock (14 December 2013). Diuresis and Diuretics / Diurese und Diuretica: An International Symposium Herrenchiemsee, June 17th–20th, 1959 Sponsored by CIBA / Ein Internationales Symposium Herrenchiemsee, 17.–20. Juni 1959 Veranstaltet mit Unterstützung der CIBA. Springer-Verlag. pp. 224,261. ISBN 978-3-642-49716-2.
- 1 2 Gyorgy Szasz; Zsuzsanna Budvari-Barany (19 December 1990). Pharmaceutical Chemistry of Antihypertensive Agents. CRC Press. pp. 82–. ISBN 978-0-8493-4724-5.
- 1 2 Dennis V. Cokkinos (6 November 2014). Introduction to Translational Cardiovascular Research. Springer. pp. 61–. ISBN 978-3-319-08798-6.
- ↑ The British Encyclopaedia of Medical Practice: Medical progress. 1961.
- ↑ Milan L. Brandon (1 January 1962). Corticosteroids in medical practice. Thomas.
- 1 2 KAGAWA CM, STURTEVANT FM, VAN ARMAN CG (1959). "Pharmacology of a new steroid that blocks salt activity of aldosterone and desoxycorticosterone". J. Pharmacol. Exp. Ther. 126 (2): 123–30. PMID 13665517.
- ↑ Janos Fischer; C. Robin Ganellin (24 August 2010). Analogue-based Drug Discovery II. John Wiley & Sons. pp. 361–. ISBN 978-3-527-63212-1.
- ↑ HERTZ R, TULLNER WW (1958). "Progestational activity of certain steroid-17-spirolactones". Proc. Soc. Exp. Biol. Med. 99 (2): 451–2. PMID 13601900.