Mespirenone Routes of administration Oral ATC code
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
CAS Number PubChem CID ChemSpider UNII ChEMBL Formula C 25 H 30 O 4 S Molar mass 426.57 g·mol−1 3D model (JSmol )
CC(=O)SC1CC2=CC(=O)C=CC2(C3C1C4C5CC5C6(C4(CC3)C)CCC(=O)O6)C
InChI=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
Key:CPHJTSJQUQZOLJ-ISIDMKFXSA-N
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]
See also [ ]
Canrenone
Drospirenone
Spironolactone
References [ ]
^ J. Elks (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, Nickisch K, Schillinger E, Wiechert R (1986). "Mespirenone and other 15,16-methylene-17-spirolactones, a new type of steroidal aldosterone antagonists". Arzneimittelforschung . 36 (11): 1583–600. PMID 3028435 .
^ Arzneimittel-Forschung . Editio Cantor. 1991.
^ a b Nishino Y, Schröder H, el Etreby MF (1988). "Experimental studies on the endocrine side effects of new aldosterone antagonists". Arzneimittelforschung . 38 (12): 1800–5. PMID 3245852 .
^ Opoku J, Kalimi M, Agarwal M, Qureshi D (1991). "Effect of a new mineralocorticoid antagonist mespirenone on aldosterone-induced hypertension". Am. J. Physiol . 260 (2 Pt 1): E269–71. doi :10.1152/ajpendo.1991.260.2.E269 . PMID 1996630 .
^ Weindel K, Lewicka S, Vecsei P (1991). "Inhibitory effects of the novel anti-aldosterone compound mespirenone on adrenocortical steroidogenesis in vitro". Arzneimittelforschung . 41 (9): 946–9. PMID 1796922 .
^ Eckhard Ottow; Hilmar Weinmann (8 September 2008). Nuclear Receptors as Drug Targets . John Wiley & Sons. pp. 410–. ISBN 978-3-527-62330-3 .
AR
Agonists
Testosterone derivatives: 4-Androstenediol
4-Dehydroepiandrosterone (4-DHEA)
4-Hydroxytestosterone
5-Androstenedione
11-Ketotestosterone
11β-Hydroxyandrostenedione
Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
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Atamestane
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AA560
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RD-162
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RU-22930
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See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens/anabolic steroids
MR
Agonists
11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)
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Nonsteroidal: Amlodipine
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Benidipine
Esaxerenone
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Finerenone
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Nitrendipine
See also
Receptor/signaling modulators
Mineralocorticoids and antimineralocorticoids
Glucocorticoid receptor modulators
List of corticosteroids
PR
Agonists
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
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Lynestrenol
Lynestrenol phenylpropionate
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RU-2309
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Trendione
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Spirolactone derivatives: Canrenoic acid
Canrenone
Drospirenone
Mespirenone
Potassium canrenoate
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SC-5233 (spirolactone)
SC-8109
Spironolactone
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Nonsteroidal: Apigenin
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Syringic acid
Antagonists
Nonsteroidal: Darolutamide
Valproic acid
mPR (PAQR )
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens