Mespirenone

Mespirenone

Clinical data
Routes of administration	Oral
ATC code	None
Identifiers
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
CAS Number	87952-98-5
PubChem CID	65660
ChemSpider	59095
UNII	E91TME2I23
ChEMBL	CHEMBL1908314
Chemical and physical data
Formula	C25H30O4S
Molar mass	426.5683 g/mol
3D model (JSmol)	Interactive image
SMILES CC(=O)SC1CC2=CC(=O)C=CC2(C3C1C4C5CC5C6(C4(CC3)C)CCC(=O)O6)C
InChI 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. Animal research found that it was 3.3-fold more potent as an antimineralocorticoid relative to spironolactone. In addition to its antimineralocorticoid properties, mespirenone is also a progestogen, antigonadotropin, and antiandrogen. 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. Mespirenone is also a potent and specific enzyme inhibitor of 18-hydroxylase and thus of mineralocorticoid biosynthesis. The drug was under development by Schering (now Bayer Schering Pharma) and reached phase II clinical trials but was discontinued in 1989.