Oxendolone

Oxendolone, sold under the brand names Prostetin and Roxenone, is an antiandrogen and progestin medication which is used in Japan in the treatment of enlarged prostate.[17] Although it is approved for the treatment of BPH in Japan, concerns have been raised about its use for this condition due to poor efficacy seen in clinical trials.[11] Oxendolone binds to the androgen receptor (Ki = 320 nM) and progesterone receptor (Ki = 20 nM) and acts as a weak but clinically relevant inhibitor of 5α-reductase (IC50Tooltip half-maximal inhibitory concentration = 1.4 μM).[16] It has been found to suppress luteinizing hormone and testosterone levels to an equivalent extent as allylestrenol and chlormadinone acetate, which are two progestins that are similarly used at high doses to treat BPH.[5] Due to its low oral bioavailability, oxendolone is administered by intramuscular injection in humans.
OxandroloneRoutes ofadministrationIntramuscular injectionDrug classSteroidal antiandrogenProgestogenProgestinPharmacokineticBioavailabilityElimination half-lifeIUPAC nameCAS NumberChemSpiderCompTox DashboardFormulaMolar massSMILESantiandrogenenlarged prostateby mouthinjection into muscleantagonistandrogen receptorbiological targettestosteronedihydrotestosteronesyntheticagonistprogesterone receptorprogesteroneantigonadotropichormonalbenign prostatic hyperplasiaclinical trialsinhibitor5α-reductaserelative binding affinitymetribolonesilent antagonistagonisticselective androgen receptor modulatorluteinizing hormoneallylestrenolchlormadinone acetateList of progestogensList of steroidal antiandrogensestranesteroidderivative19-nortestosteroneacetatecaproateTakedageneric nameMedical usesAndrogensantiandrogensagonistsAndrostenediol dipropionateBoldenone undecylenateClostebolClostebol acetateClostebol caproateClostebol propionateCloxotestosterone acetatePrasterone (dehydroepiandrosterone, DHEA)Prasterone enanthate (DHEA enanthate)Prasterone sulfate (DHEA sulfate)Quinbolonetestosterone cypionatetestosterone enanthatetestosterone propionatetestosterone undecanoatetestosterone ester mixturesDeposteronaOmnadrenSustanonTestoviron DepotAndrostanolone (stanolone, dihydrotestosterone, DHT)Bolazine capronateDrostanolone propionate (dromostanolone propionate)EpitiostanolMepitiostaneMesteroloneMetenolone acetate (methenolone acetate)Metenolone enanthate (methenolone enanthate)Stenbolone acetateBolandiol dipropionatenandrolone decanoatenandrolone phenylpropionateNorclostebolNorclostebol acetateOxabolone cipionate (oxabolone cypionate)Trenbolone acetateTrenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)BolasteroneCalusteroneChlorodehydromethyltestosterone (CDMT)FluoxymesteroneFormeboloneMetandienone (methandienone, methandrostenolone)Methandriol (methylandrostenediol)Methandriol bisenanthoyl acetateMethandriol dipropionateMethandriol propionateMethyltestosteroneMethyltestosterone 3-hexyl etherOxymesteronePenmesterolTiomesterone (thiomesterone)AndroisoxazoleFurazabolMebolazine (dimethazine)MestanoloneOxymetholoneStanozololEthylestrenolMiboleroneNorethandroloneNormethandrone (methylestrenolone, normethisterone)Propetandrol (propethandrol)Norvinisterone (vinylnortestosterone)DanazolGestrinoneProgestinsethisterone (ethynyltestosterone)levonorgestrelnorgestrelnorethisterone (norethindrone)lynestrenolnorgestrienoneTiboloneMedroxyprogesterone acetateProgonadotropinsAntiestrogenstamoxifenclomifeneGnRH agonistsGnRH (gonadorelin)leuprorelinGonadotropinsantagonistsAbiraterone acetate+niraparibCanrenoneCyproterone acetateDelmadinone acetateDienogestDrospirenoneMedrogestoneMegestrol acetateNomegestrol acetateOsaterone acetatePotassium canrenoateSpironolactoneApalutamideBicalutamideCimetidineDarolutamideEnzalutamideFlutamideKetoconazoleNilutamideSeviteronelTopilutamide (fluridil)SteroidogenesisinhibitorsAlfatradiolDutasterideEpristerideFinasterideSaw palmetto extractAminoglutethimideBifluranolAntigonadotropinsD2 receptorprolactin releasersdomperidonemetoclopramiderisperidonehaloperidolchlorpromazinesulpirideEstrogensdiethylstilbestrolestradiolethinylestradiolethinylestradiol sulfonateparoxypropioneGnRH antagonistscetrorelixProgestogenshydroxyprogesterone caproategestonorone caproateAndrovax (androstenedione albumin)Ovandrotone albumin (Fecundin)WHO-EMWithdrawnList of androgens/anabolic steroidsantiprogestogensQuingestroneDydrogesteroneTrengestoneAcetomepregenol (mepregenol diacetate)Algestone acetophenide (dihydroxyprogesterone acetophenide)Anagestone acetateChlormethenmadinone acetateFlugestone acetate (flurogestone acetate)Flumedroxone acetateHydroxyprogesterone acetateHydroxyprogesterone heptanoateMelengestrol acetateMethenmadinone acetatePentagestrone acetateProligestoneHaloprogesteroneGestonorone caproate (gestronol hexanoate)NorgestometSegesterone acetate (nestorone, elcometrine)DemegestonePromegestoneTrimegestoneDimethisteroneEthisteroneAltrenogestEtynodiol diacetateNorethisterone acetateNorethisterone enanthateNoretynodrelNorgesteroneNormethandrone (methylestrenolone)NorvinisteroneQuingestanol acetateDesogestrelEtonogestrelGestodeneNorelgestrominNorgestimateAnabolic–androgenic steroidsnandroloneesterstrenboloneTelapristoneUlipristal acetateAglepristoneMifepristone5α-Reductase inhibitors+tadalafilAlpha-1 blockersAlfuzosinDoxazosinSilodosinTamsulosinTerazosinSteroidal antiandrogensHerbal productsPygeum africanumMepartricinPharmacodynamicsmodulators4-Androstenediol4-Dehydroepiandrosterone (4-DHEA)4-Hydroxytestosterone5-Androstenedione11-Ketotestosterone11β-HydroxyandrostenedioneAdrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)Androstenediol (5-androstenediol)Androstenediol 3β-acetateAndrostenediol 17β-acetateAndrostenediol diacetateAndrostenedione (4-androstenedione)AtamestaneBoldenoneBoldione (1,4-androstadienedione)CloxotestosteroneDehydroandrosteroneDHEA (androstenolone, prasterone; 5-DHEA)DHEA enanthate (prasterone enanthate)DHEA sulfateExemestaneFormestanePlomestaneSilandrone+dutasteridePolytestosterone phloretin phosphate1-Androstenediol1-Androstenedione1-Androsterone (1-andro, 1-DHEA)1-Testosterone3α-Androstanediol5α-Androst-2-en-17-one7β-Hydroxyepiandrosterone11-KetodihydrotestosteroneAndrosteroneBolazineDihydrofluoxymesteroneDihydrotestosterone (DHT)androstanolone, stanoloneDrostanoloneDrostanolone propionateEpiandrosteroneMesaboloneMesterolone cipionateMethyldiazinolNisterimeNisterime acetateProstanozolStenboloneTestifenon (testiphenon, testiphenone)7α-Methyl-19-norandrostenedione (MENT dione, trestione)11β-Methyl-19-nortestosterone11β-Methyl-19-nortestosterone dodecylcarbonate19-Nor-5-androstenediol19-Nor-5-androstenedione19-NordehydroepiandrosteroneBolandiolBolandione (19-nor-4-androstenedione)Bolmantalate (nandrolone adamantoate)DienedioneDienoloneDimethandroloneDimethandrolone buciclateDimethandrolone dodecylcarbonateDimethandrolone undecanoateLS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate)Methoxydienone (methoxygonadiene)OxaboloneTrenbolone enanthateTrenbolone hexahydrobenzylcarbonateTrenbolone undecanoateTrendioneTrestolone (MENT)Trestolone acetateTrestolone enanthate5α-Dihydronandrolone19-NorandrosteroneChlorodehydromethylandrostenediol (CDMA)Chloromethylandrostenediol (CMA)EnestebolEthyltestosteroneHydroxystenozoleMetandienone (methandrostenolone)Methandriol diacetateMethylclostebol (chloromethyltestosterone)+esterified estrogensTiomesteroneDesoxymethyltestosteroneMetenoloneMetenolone acetateMetenolone enanthateMethasteroneMethyl-1-testosteroneMethylepitiostanolMethylstenboloneBolenolDimethyldienoloneDimethyltrienoloneEthyldienoloneMethyldienoloneMethylhydroxynandrolone (MOHN, MHN)NorboletonePropetandrolRU-2309Tetrahydrogestrinone5α-Dihydronorethandrolone5α-DihydronormethandroneVinyltestosteroneEthinylandrostenediolEthandrostate17α-Ethynyl-3α-androstanediol17α-Ethynyl-3β-androstanediolDihydroethisteroneΔ4-TiboloneEtynodiolLevonorgestrel esterslevonorgestrel butanoateLynestrenol phenylpropionateNorethisteroneNorethisterone estersQuingestanol5α-Dihydrolevonorgestrel5α-Dihydronorethisterone6α-Methylprogesterone3-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 acetateAbirateroneAllyltestosteroneBenorteroneCanrenoic acidClascoteroneClometeroneCyproheptadineCyproteroneDelanteroneDicirenoneDU-41165EdogestroneEM-5854EpitestosteroneGaleteroneGuggulsteroneMespirenoneMetogestMexrenoneNordinoneOsateroneProrenoneRosteroloneSC-5233 (spirolactone)SpirorenoneSpiroxasoneTopteroneTrimethyltrienolone (R-2956)Zanoterone5N-BicalutamideAtraric acidBakuchiolBavdegalutamideBisphenolsbisphenol Abisphenol Fbisphenol SBMS-641988CioteronelCyanonilutamidep,p’-DDEDieldrinEndosulfanEPI-001FenarimolHydroxyflutamideInocoteroneInocoterone acetateKetodarolutamideLavender oilLG-120907LinuronMasofanitenMethiocarbN-DesmethylapalutamideN-DesmethylenzalutamidePentomonePhenothrinProchlorazProcymidoneProxalutamidePyrilutamideRalaniten (EPI-002)Ralaniten acetate (EPI-506)RD-162RezvilutamideRU-22930RU-56187RU-57073RU-58642RU-58841ThalidomideValproic acidVinclozolinGPRC6ACationsaluminiumcalciumgadoliniummagnesiumstrontiumL-α-Amino acidsL-arginineL-lysineL-ornithineOsteocalcinList of androgens and anabolic steroids3β-Dihydroprogesterone5α-Dihydroprogesterone9α-Bromo-11-ketoprogesterone11-Dehydroprogesterone11-Deoxycorticosterone16α-Hydroxyprogesterone20α-Dihydroprogesterone20β-DihydroprogesteroneDimepregnenDiosgeninP1-185Progesterone 3-acetyl enol ether20α-Dihydrodydrogesterone20α-DihydrotrengestoneDU-41164RetroprogesteroneRo 6-31296α-Methyl-17α-bromoprogesterone16-Methylene-17α-hydroxyprogesterone acetate17α-Bromoprogesterone17α-Hydroxyprogesterone (hydroxyprogesterone)17α-MethylprogesteroneAlgestoneAlgestone acetonideAlgestone acetophenideAnagestoneBromethenmadinone acetateButagest (buterol)ChlormadinoneChlormadinone caproateCismadinoneCismadinone acetateClogestoneClogestone acetateClomegestoneClomegestone acetateCymegesolateDelmadinoneFlugestoneFlugestone acetateFluorometholoneFluorometholone acetateFlumedroxoneFluoromedroxyprogesterone acetateGestacloneHydromadinoneHydromadinone acetateHydroxyprogesterone caproate (hydroxyprogesterone hexanoate)Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)Hydroxyprogesterone heptanoate benzilic acid hydrazoneMecigestone (pentarane B)MedroxyprogesteroneMedroxyprogesterone caproateMegestrolMegestrol caproateMelengestrolMethenmadinoneMethenmadinone caproateMometasoneMometasone furoatePentagestronePentarane ATriamcinolone acetonide17α-Methyl-19-norprogesterone18-Methylsegesterone acetate19-NorprogesteroneAmadinoneAmadinone acetateGestadienolGestadienol acetateGestonorone acetate (gestronol acetate)Gestronol (gestonorone)NomegestrolORG-2058OxogestoneOxogestone phenpropionate (xinogestone)SegesteroneSegesterone acetate (nestorone)6,6-Difluoronorethisterone6,6-Difluoronorethisterone acetate17α-Allyl-19-nortestosteroneChloroethynylnorgestrelCingestolEthyneroneMetynodiolMetynodiol diacetateTigestolTosagestinBolandioneEthylestrenol (ethylnandrol)Metribolone (R-1881)Nandrolone estersNormethandrone (methylestrenolone, normethandrolone, normethisterone)Trenbolone (trienolone)Trenbolone estersTrestoloneSC-81093,8-DihydrodiligustilideLG-2527RiligustilideTanaprogetORG-47241ORG-201745AsoprisnilAsoprisnil ecamateMetapristone (RU-42633)Mifepristone (RU-486)ORF-9326VilaprisanApigeninKaempferolNaringeninSyringic acidLilopristoneLonaprisanOnapristoneToripristone5β-Dihydroprogesterone11-Deoxycortisone (21-hydroxyprogesterone)11-Deoxycortisol (17α,21-dihydroxyprogesterone)17α-HydroxyprogesteroneAllopregnanolonePregnenolone