Dimethandrolone undecanoate

Dimethandrolone undecanoate (DMAU), also known by its developmental code name CDB-4521, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under development as a potential birth control pill for men.[2][3][4] The medication has been found to profoundly and rapidly reversibly suppress testicular testosterone production in men when taken by mouth once per day for a month.[5][10] In addition to male contraception, there has also been interest in the potential use of DMAU in androgen replacement therapy for low testosterone levels in men.[18][19][14][8] Reduced sexual function and decreased bone mineral density have been observed with the closely related medication trestolone, which has low estrogenicity similarly to DMAU.[14][20][8] Unlike testosterone but similarly to 17α-alkyated AAS like methyltestosterone (17α-methyltestosterone), DMAU has been found to produce some effects indicative of potential liver toxicity when it was administered orally to animals.[15] A pharmacokinetic study of DMAU in men found that only 2 to 3% of the drug was hydrolyzed into dimethandrolone when it was administered orally in the form of powder in capsules.[3] Although the hydrolysis of DMAU into dimethandrolone was very limited, it was still sufficient to produce dose-dependent biological effects at the dosages assessed, including reversible suppression of luteinizing hormone and testosterone levels.
Routes ofadministrationBy mouthintramuscular injectionDrug classAndrogenAnabolic steroidAndrogen esterProgestogenIUPAC nameCAS NumberDrugBankChemSpiderFormulaMolar massSMILESexperimentalbirth control pillfor meninjection into muscleSide effectsweight gainHDL cholesterollow estrogen levelssymptomsreduced sexual functiondecreased bone mineral densityagonistandrogen receptorbiological targettestosteroneprogestinsyntheticprogesterone receptorprogesteroneantigonadotropicsperm productioncontraceptiveestrogenicprodrugdimethandroloneNational Institute of Child Health and Human DevelopmentUnited States governmentmale hormonal contraceptivetesticularproductionsurgical castrationspermatogenesisfertilityandrogen replacement therapylow testosterone levelswell tolerated5α-reducedscalp hair lossestrogensexual dysfunctiondecreased sex drivereduced erectile functionosteoporosisbone mineral densitytrestolone17α-alkyatedmethyltestosteroneliver toxicity11β-methyl-19-nortestosterone 17β-dodecylcarbonatekidneyhormonal contraceptivearomatizedsubstrate5α-reductasetissueshair folliclesprostate glandandrogenicandrogen-dependent conditionspattern scalp hair lossbody hair growthbenign prostatic hyperplasiaprostate cancerpharmacokinetichydrolyzedcapsulestestosterone undecanoatesteric hindrancemethyl groupsluteinizing hormonecastor oilbenzyl benzoateself-emulsifying drug delivery systemList of androgens/anabolic steroidsList of androgen estersestranesteroid17α-alkylatedderivative19-nortestosteroneundecanoatedimethandrolone buciclatedimethandrolone dodecylcarbonatetrestolone acetatepatentNational Institutes of HealthUnited States Department of Health and Human ServicesLive ScienceNBC NewsChicago Tribunemodulators4-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 sulfateExemestaneFormestanePlomestaneQuinboloneSilandrone+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)DienedioneDienoloneLS-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 enanthate5α-Dihydronandrolone19-NorandrosteroneBolasteroneCalusteroneChlorodehydromethylandrostenediol (CDMA)Chlorodehydromethyltestosterone (CDMT)Chloromethylandrostenediol (CMA)EnestebolEthyltestosteroneFluoxymesteroneFormeboloneHydroxystenozoleMetandienone (methandrostenolone)Methandriol (methylandrostenediol)Methandriol bisenanthoyl acetateMethandriol diacetateMethandriol dipropionateMethandriol propionateMethylclostebol (chloromethyltestosterone)+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 acidCanrenoneChlormadinone acetateClascoteroneClometeroneCyproheptadineCyproteroneCyproterone acetateDelanteroneDelmadinone acetateDicirenoneDienogestDrospirenoneDU-41165EdogestroneEM-5854EpitestosteroneGaleteroneGuggulsteroneMedrogestoneMespirenoneMetogestMexrenoneMifepristoneNomegestrol acetateNordinoneOsateroneOsaterone acetateOxendolonePotassium canrenoatePromegestoneProrenoneRosteroloneSC-5233 (spirolactone)SpironolactoneSpirorenoneSpiroxasoneTopteroneTrimegestoneTrimethyltrienolone (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 steroids3β-Dihydroprogesterone5α-Dihydroprogesterone9α-Bromo-11-ketoprogesterone11-Dehydroprogesterone11-Deoxycorticosterone16α-Hydroxyprogesterone20α-Dihydroprogesterone20β-DihydroprogesteroneDimepregnenDiosgeninP1-185Progesterone 3-acetyl enol etherQuingestrone20α-Dihydrodydrogesterone20α-DihydrotrengestoneDU-41164DydrogesteroneRetroprogesteroneRo 6-3129Trengestone6α-Methyl-17α-bromoprogesterone16-Methylene-17α-hydroxyprogesterone acetate17α-Bromoprogesterone17α-Hydroxyprogesterone (hydroxyprogesterone)17α-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 caproateMometasoneMometasone furoatePentagestronePentagestrone acetatePentarane AProligestoneTriamcinolone acetonide17α-Methyl-19-norprogesterone18-Methylsegesterone acetate19-NorprogesteroneAmadinoneAmadinone 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)NoretynodrelNorgesteroneNorgestimateNorvinisteroneTigestolTosagestinBolandioneDimethisteroneEthylestrenol (ethylnandrol)Metribolone (R-1881)Nandrolone estersnandrolone decanoatenandrolone phenylpropionateNormethandrone (methylestrenolone, normethandrolone, normethisterone)Trenbolone (trienolone)Trenbolone estersSC-81093,8-DihydrodiligustilideLG-2527RiligustilideTanaprogetORG-47241ORG-201745AsoprisnilAsoprisnil ecamateMetapristone (RU-42633)Mifepristone (RU-486)ORF-9326TelapristoneUlipristal acetateVilaprisanApigeninKaempferolNaringeninSyringic acidAglepristoneLilopristoneLonaprisanOnapristoneToripristone5β-Dihydroprogesterone11-Deoxycortisone (21-hydroxyprogesterone)11-Deoxycortisol (17α,21-dihydroxyprogesterone)17α-HydroxyprogesteroneAllopregnanolonePregnenoloneList of progestogens