mespirenone

{{Short description|Chemical compound}}

{{Use dmy dates|date=April 2017}}

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| IUPAC_name = S-[(4aR,4bS,6aS,7S,7aS,8aS,8bS,8cR,9R)-4a,6a-Dimethyl-2,5'-dioxo-2,4',4b,5,5',6,6a,7a,8,8a,8b,8c,9,10-tetradecahydro-3'H,4aH-spiro[cyclopropa[4,5]cyclopenta[1,2-a]phenanthrene-7,2'-furan]-9-yl]ethane thioate

| image = Mespirenone.svg

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| routes_of_administration = Oral

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| CAS_number = 87952-98-5

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| ATC_prefix = None

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| PubChem = 65660

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| ChemSpiderID = 59095

| ChEMBL = 1908314

| UNII = E91TME2I23

| C=25 | H=30 | O=4 | S=1

| smiles = CC(=O)SC1CC2=CC(=O)C=CC2(C3C1C4C5CC5C6(C4(CC3)C)CCC(=O)O6)C

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| StdInChI = InChI=1S/C25H30O4S/c1-13(26)30-19-11-14-10-15(27)4-7-23(14,2)17-5-8-24(3)22(21(17)19)16-12-18(16)25(24)9-6-20(28)29-25/h4,7,10,16-19,21-22H,5-6,8-9,11-12H2,1-3H3/t16-,17+,18+,19-,21+,22+,23+,24+,25+/m1/s1

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| StdInChIKey = CPHJTSJQUQZOLJ-ISIDMKFXSA-N

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Mespirenone (INN; developmental code ZK-94679; also known as Δ¹-15β,16β-methylenespironolactone) is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone that was never marketed.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA775|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=775–}}{{cite journal | vauthors = Losert W, Bittler D, Buse M, Casals-Stenzel J, Haberey M, Laurent H, Nickisch K, Schillinger E, Wiechert R | display-authors = 6 | title = Mespirenone and other 15,16-methylene-17-spirolactones, a new type of steroidal aldosterone antagonists | journal = Arzneimittel-Forschung | volume = 36 | issue = 11 | pages = 1583–1600 | date = November 1986 | pmid = 3028435 }} Animal research found that it was 3.3-fold more potent as an antimineralocorticoid relative to spironolactone.{{cite journal | vauthors = Weindel K, Lewicka S, Vecsei P | title = Interference of C17-spirosteroids with late steps of aldosterone biosynthesis. Structure-activity studies | journal = Arzneimittel-Forschung | volume = 41 | issue = 10 | pages = 1082–1091 (1083) | date = October 1991 | pmid = 1799390 | doi = | url = https://books.google.com/books?id=QtcTAQAAMAAJ }} In addition to its antimineralocorticoid properties, mespirenone is also a progestogen, antigonadotropin, and antiandrogen.{{cite journal | vauthors = Nishino Y, Schröder H, el Etreby MF | title = Experimental studies on the endocrine side effects of new aldosterone antagonists | journal = Arzneimittel-Forschung | volume = 38 | issue = 12 | pages = 1800–1805 | date = December 1988 | pmid = 3245852 }} 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.{{cite journal | vauthors = Opoku J, Kalimi M, Agarwal M, Qureshi D | title = Effect of a new mineralocorticoid antagonist mespirenone on aldosterone-induced hypertension | journal = The American Journal of Physiology | volume = 260 | issue = 2 Pt 1 | pages = E269–E271 | date = February 1991 | pmid = 1996630 | doi = 10.1152/ajpendo.1991.260.2.E269 }} Mespirenone is also a potent and specific enzyme inhibitor of 18-hydroxylase and thus of mineralocorticoid biosynthesis.{{cite journal | vauthors = Weindel K, Lewicka S, Vecsei P | title = Inhibitory effects of the novel anti-aldosterone compound mespirenone on adrenocortical steroidogenesis in vitro | journal = Arzneimittel-Forschung | volume = 41 | issue = 9 | pages = 946–949 | date = September 1991 | pmid = 1796922 }} The drug was under development by Schering (now Bayer Schering Pharma) and reached phase II clinical trials but was discontinued in 1989.{{cite book| vauthors = Kolkhof P, Bärfacker L, Hillisch A, Haning H, Schäfer S | chapter = Nuclear receptors as targets in cardiovascular diseases | veditors = Ottow E, Weinmann H |title=Nuclear Receptors as Drug Targets | chapter-url = https://books.google.com/books?id=iATfLbPgRugC&pg=PA410 |date=8 September 2008|publisher=John Wiley & Sons|isbn=978-3-527-62330-3|pages=410–}}