Mespirenone (INN) (developmental code name ZK-94679), also known as Δ1-15β,16β-methylenespironolactone, is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone that was never marketed.[1][2] Animal research found that it was 3.3-fold more potent as an antimineralocorticoid relative to spironolactone.[3] In addition to its antimineralocorticoid properties, mespirenone is also a progestogen, antigonadotropin, and antiandrogen.[2][4] It is 2- to 3-fold as potent as spironolactone as a progestogen and antigonadotropin but its antiandrogenic activity is markedly reduced and weak (though still of significance) in comparison.[4][5] Mespirenone is also a potent and specific enzyme inhibitor of 18-hydroxylase and thus of mineralocorticoid biosynthesis.[6] The drug was under development by Schering (now Bayer Schering Pharma) and reached phase II clinical trials but was discontinued in 1989.[7]
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| Routes of administration | Oral |
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| Formula | C25H30O4S |
| Molar mass | 426.57 g·mol−1 |
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See also
editReferences
edit- ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 775–. ISBN 978-1-4757-2085-3.
- ^ a b Losert W, Bittler D, Buse M, Casals-Stenzel J, Haberey M, Laurent H, et al. (November 1986). "Mespirenone and other 15,16-methylene-17-spirolactones, a new type of steroidal aldosterone antagonists". Arzneimittel-Forschung. 36 (11): 1583–1600. PMID 3028435.
- ^ Weindel K, Lewicka S, Vecsei P (October 1991). "Interference of C17-spirosteroids with late steps of aldosterone biosynthesis. Structure-activity studies". Arzneimittel-Forschung. 41 (10): 1082–1091 (1083). PMID 1799390.
- ^ a b Nishino Y, Schröder H, el Etreby MF (December 1988). "Experimental studies on the endocrine side effects of new aldosterone antagonists". Arzneimittel-Forschung. 38 (12): 1800–1805. PMID 3245852.
- ^ Opoku J, Kalimi M, Agarwal M, Qureshi D (February 1991). "Effect of a new mineralocorticoid antagonist mespirenone on aldosterone-induced hypertension". The American Journal of Physiology. 260 (2 Pt 1): E269–E271. doi:10.1152/ajpendo.1991.260.2.E269. PMID 1996630.
- ^ Weindel K, Lewicka S, Vecsei P (September 1991). "Inhibitory effects of the novel anti-aldosterone compound mespirenone on adrenocortical steroidogenesis in vitro". Arzneimittel-Forschung. 41 (9): 946–949. PMID 1796922.
- ^ Kolkhof P, Bärfacker L, Hillisch A, Haning H, Schäfer S (8 September 2008). "Nuclear receptors as targets in cardiovascular diseases". In Ottow E, Weinmann H (eds.). Nuclear Receptors as Drug Targets. John Wiley & Sons. pp. 410–. ISBN 978-3-527-62330-3.
