Mespirenone

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.
Routes ofadministrationATC codeIUPAC nameCAS NumberChemSpiderChEMBLCompTox DashboardFormulaMolar massSMILESsteroidalantimineralocorticoidspirolactonespironolactoneprogestogenantigonadotropinantiandrogenpotentenzyme inhibitor18-hydroxylasemineralocorticoidbiosynthesisScheringBayer Schering Pharmaclinical trialsCanrenoneDrospirenoneAndrogen receptormodulators4-Androstenediol4-Dehydroepiandrosterone (4-DHEA)4-Hydroxytestosterone5-Androstenedione11-Ketotestosterone11β-HydroxyandrostenedioneAdrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)Androstenediol (5-androstenediol)Androstenediol 3β-acetateAndrostenediol 17β-acetateAndrostenediol diacetateAndrostenediol dipropionateAndrostenedione (4-androstenedione)AtamestaneBoldenoneBoldenone undecylenateBoldione (1,4-androstadienedione)ClostebolClostebol acetateClostebol caproateClostebol propionateCloxotestosteroneCloxotestosterone acetateDehydroandrosteroneDHEA (androstenolone, prasterone; 5-DHEA)DHEA enanthate (prasterone enanthate)DHEA sulfateExemestaneFormestanePlomestaneQuinboloneSilandroneTestosterone+dutasteridePolytestosterone phloretin phosphate1-Androstenediol1-Androstenedione1-Androsterone (1-andro, 1-DHEA)1-Testosterone3α-Androstanediol5α-Androst-2-en-17-one7β-Hydroxyepiandrosterone11-KetodihydrotestosteroneAndrosteroneBolazineBolazine capronateDihydrofluoxymesteroneDihydrotestosterone (DHT)androstanolone, stanoloneDrostanoloneDrostanolone propionateEpiandrosteroneEpitiostanolMepitiostaneMesaboloneMesteroloneMesterolone cipionateMethyldiazinolNisterimeNisterime acetateProstanozolStenboloneStenbolone acetateTestifenon (testiphenon, testiphenone)7α-Methyl-19-norandrostenedione (MENT dione, trestione)11β-Methyl-19-nortestosterone11β-Methyl-19-nortestosterone dodecylcarbonate19-Nor-5-androstenediol19-Nor-5-androstenedione19-NordehydroepiandrosteroneBolandiolBolandiol dipropionateBolandione (19-nor-4-androstenedione)Bolmantalate (nandrolone adamantoate)DienedioneDienoloneDimethandroloneDimethandrolone buciclateDimethandrolone dodecylcarbonateDimethandrolone undecanoateLS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate)Methoxydienone (methoxygonadiene)NandroloneNorclostebolNorclostebol acetateNormethandrone (methylestrenolone, normethisterone)OxaboloneOxabolone cipionate (oxabolone cypionate)TrenboloneTrenbolone acetateTrenbolone enanthateTrenbolone hexahydrobenzylcarbonateTrenbolone undecanoateTrendioneTrestolone (MENT)Trestolone acetateTrestolone enanthate5α-Dihydronandrolone19-NorandrosteroneBolasteroneCalusteroneChlorodehydromethylandrostenediol (CDMA)Chlorodehydromethyltestosterone (CDMT)Chloromethylandrostenediol (CMA)EnestebolEthyltestosteroneFluoxymesteroneFormeboloneHydroxystenozoleMetandienone (methandrostenolone)Methandriol (methylandrostenediol)Methandriol bisenanthoyl acetateMethandriol diacetateMethandriol dipropionateMethandriol propionateMethylclostebol (chloromethyltestosterone)Methyltestosterone+esterified estrogensMethyltestosterone 3-hexyl etherOxymesteronePenmesterolTiomesteroneAndroisoxazoleDesoxymethyltestosteroneFurazabolMebolazine (dimethazine)MestanoloneMetenoloneMetenolone acetateMetenolone enanthateMethasteroneMethyl-1-testosteroneMethylepitiostanolMethylstenboloneOxandroloneOxymetholoneStanozololBolenolDimethyldienoloneDimethyltrienoloneEthyldienoloneEthylestrenolMethyldienoloneMethylhydroxynandrolone (MOHN, MHN)MetriboloneMiboleroneNorboletoneNorethandrolonePropetandrolRU-2309Tetrahydrogestrinone5α-Dihydronorethandrolone5α-DihydronormethandroneNorvinisterone (vinylnortestosterone)VinyltestosteroneDanazolEthinylandrostenediolEthandrostateEthisterone (ethynyltestosterone)17α-Ethynyl-3α-androstanediol17α-Ethynyl-3β-androstanediolDihydroethisteroneΔ4-TiboloneDesogestrelEtonogestrelEtynodiolEtynodiol diacetateGestodeneGestrinoneLevonorgestrelLevonorgestrel esterslevonorgestrel butanoateLynestrenolLynestrenol phenylpropionateNorethisteroneNorethisterone estersnorethisterone acetatenorethisterone enanthateNorgestrelNorgestrienoneQuingestanolQuingestanol acetateTibolone5α-Dihydrolevonorgestrel5α-Dihydronorethisterone6α-MethylprogesteroneMedroxyprogesterone acetateMegestrol acetate3-Keto-5α-abiraterone5α-AndrostaneAlternariolCl-4AS-1DrupanolTrilostaneZM-182345ACP-105AC-262,536AcetothiolutamideAcetoxolutamideAndarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)BMS-564,929Enobosarm (ostarine, MK-2866, GTx-024, S-22)GLPG-0492GSK2881078GSK-4336ALG121071 (LGD-121071)LGD-2226LGD-2941 (LGD-122941)LGD-3303LGD-4033JNJ-26146900JNJ-28330835JNJ-37654032OPK-88004 (LY-2452473, TT-701)PF-06260414RU-59063S-40503VosilasarmMK-0773TFM-4AS-17α-Thioprogesterone7α-Thiospironolactone7α-Thiomethylspironolactone11α-Hydroxyprogesterone15β-Hydroxycyproterone acetateAbirateroneAbiraterone acetateAllyltestosteroneBenorteroneCanrenoic acidChlormadinone acetateClascoteroneClometeroneCyproheptadineCyproteroneCyproterone acetateDelanteroneDelmadinone acetateDicirenoneDienogestDU-41165EdogestroneEM-5854EpitestosteroneGaleteroneGuggulsteroneMedrogestoneMetogestMexrenoneMifepristoneNomegestrol acetateNordinoneOsateroneOsaterone acetateOxendolonePotassium canrenoatePromegestoneProrenoneRosteroloneSC-5233 (spirolactone)SpirorenoneSpiroxasoneTopteroneTrimegestoneTrimethyltrienolone (R-2956)Zanoterone5N-BicalutamideApalutamideAtraric acidBakuchiolBavdegalutamideBicalutamideBisphenolsbisphenol Abisphenol Fbisphenol SBMS-641988CimetidineCioteronelCyanonilutamideDarolutamidep,p’-DDEDieldrinEndosulfanEnzalutamideEPI-001FenarimolFlutamideHydroxyflutamideInocoteroneInocoterone acetateKetoconazoleKetodarolutamideLavender oilLG-120907LinuronMasofanitenMethiocarbN-DesmethylapalutamideN-DesmethylenzalutamideNilutamidePentomonePhenothrinProchlorazProcymidoneProxalutamidePyrilutamideRalaniten (EPI-002)Ralaniten acetate (EPI-506)RD-162RezvilutamideRU-22930RU-56187RU-57073RU-58642RU-58841SeviteronelThalidomideTopilutamide (fluridil)Valproic acidVinclozolinGPRC6ACationsaluminiumcalciumgadoliniummagnesiumstrontiumDihydrotestosteroneEstradiolL-α-Amino acidsL-arginineL-lysineL-ornithineOsteocalcinList of androgens and anabolic steroidsMineralocorticoid receptor11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)11-Deoxycortisol (cortodoxone, cortexolone)Cortifen (cortiphen, kortifen)11β-Hydroxyprogesterone18-Hydroxy-11-deoxycorticosterone19-NorprogesteroneAldosteroneCorticosteroneCortisolhydrocortisoneBenzodrocortisone (hydrocortisone benzoate)Hydrocortamate (hydrocortisone diethylaminoacetate)CortisoneCortisone acetateFludrocortisone (fludrocortone)Fludrocortisone acetateMometasoneMometasone furoatePrednisolonePrednazatePrednazolinePrednicarbate (prednisolone ethylcarbonate propionate)PrednimustinePrednisolamate (prednisolone diethylaminoacetate)Prednisone6β-Hydroxy-7α-thiomethylspironolactone7α-Thiomethylspironolactone (SC-26519)7α-Thioprogesterone (SC-8365)7α-Thiospironolactone (SC-24813)16α-Hydroxyprogesterone17α-Hydroxyprogesterone (hydroxyprogesterone)18-DeoxyaldosteroneCanrenoate potassium (potassium canrenoate)Canrenoic acid (canrenoate)Canrenone (canrenoate y-lactone)DimethisteroneDydrogesteroneEplerenoneHydroxyprogesterone caproateMexrenoate potassiumMexrenoic acid (mexrenoate)Oxprenoic acid (oxprenoate)Oxprenoate potassium (RU-28318)PregnenoloneProgesteroneProrenoate potassiumProrenoic acid (prorenoate)SC-8109VamoroloneAmlodipineApararenoneBenidipineEsaxerenoneFelodipineFinerenoneMiricorilant (CORT-118335)NifedipineNimodipineNitrendipineOcedurenoneList of corticosteroidsProgesterone receptor3β-Dihydroprogesterone5α-Dihydroprogesterone9α-Bromo-11-ketoprogesterone11-Dehydroprogesterone11-Deoxycorticosterone20α-Dihydroprogesterone20β-DihydroprogesteroneDimepregnenDiosgeninP1-185Progesterone 3-acetyl enol etherQuingestrone20α-Dihydrodydrogesterone20α-DihydrotrengestoneDU-41164RetroprogesteroneRo 6-3129Trengestone6α-Methyl-17α-bromoprogesterone16-Methylene-17α-hydroxyprogesterone acetate17α-Bromoprogesterone17α-MethylprogesteroneAcetomepregenol (mepregenol diacetate)AlgestoneAlgestone acetonideAlgestone acetophenideAnagestoneAnagestone acetateBromethenmadinone acetateButagest (buterol)ChlormadinoneChlormadinone caproateChlormethenmadinone acetateCismadinoneCismadinone acetateClogestoneClogestone acetateClomegestoneClomegestone acetateCymegesolateDelmadinoneFlugestoneFlugestone acetateFluorometholoneFluorometholone acetateFlumedroxoneFlumedroxone acetateFluoromedroxyprogesterone acetateGestacloneHaloprogesteroneHydromadinoneHydromadinone acetateHydroxyprogesterone acetateHydroxyprogesterone caproate (hydroxyprogesterone hexanoate)Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)Hydroxyprogesterone heptanoate benzilic acid hydrazoneMecigestone (pentarane B)MedroxyprogesteroneMedroxyprogesterone caproateMegestrolMegestrol caproateMelengestrolMelengestrol acetateMethenmadinoneMethenmadinone acetateMethenmadinone caproatePentagestronePentagestrone acetatePentarane AProligestoneTriamcinolone acetonide17α-Methyl-19-norprogesterone18-Methylsegesterone acetateAmadinoneAmadinone acetateDemegestoneGestadienolGestadienol acetateGestonorone acetate (gestronol acetate)Gestonorone caproate (gestronol hexanoate)Gestronol (gestonorone)NomegestrolNorgestometORG-2058OxogestoneOxogestone phenpropionate (xinogestone)SegesteroneSegesterone acetate (nestorone)6,6-Difluoronorethisterone6,6-Difluoronorethisterone acetate17α-Allyl-19-nortestosteroneAllylestrenolAltrenogestChloroethynylnorgestrelCingestolEthisteroneEthyneroneMetynodiolMetynodiol diacetateNorelgestrominNorethisterone (norethindrone)NoretynodrelNorgesteroneNorgestimateNorvinisteroneTigestolTosagestinBolandioneEthylestrenol (ethylnandrol)Metribolone (R-1881)Nandrolone estersnandrolone decanoatenandrolone phenylpropionateNormethandrone (methylestrenolone, normethandrolone, normethisterone)Trenbolone (trienolone)Trenbolone estersTrestolone3,8-DihydrodiligustilideLG-2527RiligustilideTanaprogetORG-47241ORG-201745AsoprisnilAsoprisnil ecamateMetapristone (RU-42633)Mifepristone (RU-486)ORF-9326TelapristoneUlipristal acetateVilaprisanApigeninKaempferolNaringeninSyringic acidAglepristoneLilopristoneLonaprisanOnapristoneToripristone5β-Dihydroprogesterone11-Deoxycortisone (21-hydroxyprogesterone)11-Deoxycortisol (17α,21-dihydroxyprogesterone)17α-HydroxyprogesteroneAllopregnanoloneList of progestogenssteroid