Gestrinone

[3][4] It has also been used to treat other conditions such as uterine fibroids and heavy menstrual bleeding and has been investigated as a method of birth control.[5][6] Due to its antigonadotropic effects and ability to inhibit ovulation, gestrinone has been studied as a method of hormonal birth control in women.It is also contraindicated in patients who experienced metabolic and/or vascular disorders during previous estrogen or progestogen therapy, or who are allergic to the medication.[1][10] In one study of 2.5 mg oral gestrinone twice per week in women, it caused seborrhea in 71%, acne in 65%, breast hypoplasia in 29%, hirsutism in 9%, and scalp hair loss in 9%.[1] Other androgenic side effects that have been reported include oily skin and hair, weight gain, voice deepening, and clitoral enlargement, the latter two of which as well as hirsutism may be irreversible.[1][18][21] In addition to the PR and AR, gestrinone has been found to bind to the estrogen receptor (ER) with relatively "avid" affinity.[32][33] The androgenic properties of gestrinone are more exploited in its derivative tetrahydrogestrinone (THG; 17α-ethyl-18-methyl-δ9,11-19-nortestosterone), a designer steroid which is far more potent as both an AAS and progestogen in comparison.[27][15][7] Gestrinone is or has been marketed in Europe, Australia, Latin America, and Southeast Asia,[15][7] though notably not in the United States.
Drugs.comPregnancycategoryRoutes ofadministrationBy mouthvaginalDrug classProgestogenProgestinAntiprogestogenAndrogenAnabolic steroidSteroidogenesis inhibitorAntiestrogenATC codeG03XA02Legal statusPharmacokineticProtein bindingalbuminMetabolismhydroxylationElimination half-lifeExcretionIUPAC nameCAS NumberDrugBankChemSpiderChEMBLCompTox DashboardECHA InfoCardFormulaMolar massSMILESendometriosisuterine fibroidsheavy menstrual bleedingbirth controlin through the vaginaSide effectsmenstrual abnormalitiesestrogen deficiencysymptomsmasculinizationseborrheabreast shrinkageincreased hair growthscalp hair lossmechanism of actionantigonadotropinEuropeUnited StatesanabolicInternational Olympic Committeedanazolmenorrhagiaantigonadotropicovulationhormonal birth controlmenstrual cyclespregnancyemergency post-coital contraceptivecontraindicatedlactationchronic kidney diseaseandrogenicantiestrogenicbreast hypoplasiahirsutismoily skinweight gainvoice deepeningclitoral enlargementgonadotropinsecretionamenorrheaoligomenorrheaestradiolaffinityprogesterone receptorandrogen receptorprogestogenicantiprogestogenicpartial agonistselective progesterone receptor modulatoragonistanabolic–androgenic steroidpituitary glandluteinizing hormonefollicle-stimulating hormonemenstrual cycleovariansteroidogenesissex hormone-binding globulintestosteroneestrogen receptorendometriumcorticosteroid-binding globulinNorethisteroneNorgestrienoneLevonorgestrelligandsprogesteronealdosteronecortisolmetabolizedactive metabolitesexcretedList of progestogensList of androgens/anabolic steroidssyntheticestranesteroidderivativegonane19-nortestosteronemethylanalogueethynyltrenbolonetetrahydrogestrinonedesigner steroidFood and Drug Administrationgeneric nameAustraliaLatin AmericaSoutheast AsiaAnvisaDiário Oficial da UniãoAndrogensantiandrogensagonistsAndrostenediol 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)MestanoloneOxandroloneOxymetholoneStanozololEthylestrenolMiboleroneNorethandroloneNormethandrone (methylestrenolone, normethisterone)Propetandrol (propethandrol)Norvinisterone (vinylnortestosterone)Progestinsethisterone (ethynyltestosterone)norgestrelnorethisterone (norethindrone)lynestrenolTiboloneMedroxyprogesterone acetateProgonadotropinsAntiestrogenstamoxifenclomifeneGnRH agonistsGnRH (gonadorelin)leuprorelinGonadotropinsantagonistsAbiraterone acetate+niraparibCanrenoneChlormadinone acetateCyproterone acetateDelmadinone acetateDienogestDrospirenoneMedrogestoneMegestrol acetateNomegestrol acetateOsaterone acetateOxendolonePotassium canrenoateSpironolactoneApalutamideBicalutamideCimetidineDarolutamideEnzalutamideFlutamideKetoconazoleNilutamideSeviteronelTopilutamide (fluridil)Steroidogenesisinhibitors5α-ReductaseAlfatradiolDutasterideEpristerideFinasterideSaw palmetto extractAminoglutethimideBifluranolAntigonadotropinsD2 receptorprolactin releasersdomperidonemetoclopramiderisperidonehaloperidolchlorpromazinesulpirideEstrogensdiethylstilbestrolethinylestradiolethinylestradiol sulfonateparoxypropioneGnRH antagonistscetrorelixProgestogenshydroxyprogesterone caproategestonorone caproateAndrovax (androstenedione albumin)Ovandrotone albumin (Fecundin)WHO-EMWithdrawnClinical trialsantiprogestogensQuingestroneDydrogesteroneTrengestoneAcetomepregenol (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)DemegestonePromegestoneTrimegestoneDimethisteroneEthisteroneAllylestrenolAltrenogestEtynodiol diacetateNorethisterone acetateNorethisterone enanthateNoretynodrelNorgesteroneNormethandrone (methylestrenolone)NorvinisteroneQuingestanol acetateDesogestrelEtonogestrelGestodeneNorelgestrominNorgestimateAnabolic–androgenic steroidsnandroloneestersTelapristoneUlipristal acetateAglepristoneMifepristonemodulators4-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 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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)MetriboloneNorboletonePropetandrolRU-23095α-Dihydronorethandrolone5α-DihydronormethandroneVinyltestosteroneEthinylandrostenediolEthandrostate17α-Ethynyl-3α-androstanediol17α-Ethynyl-3β-androstanediolDihydroethisteroneΔ4-TiboloneEtynodiolLevonorgestrel esterslevonorgestrel butanoateLynestrenol phenylpropionateNorethisterone 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 acidVinclozolinGPRC6ACationsaluminiumcalciumgadoliniummagnesiumstrontiumDihydrotestosteroneL-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-HydroxyprogesteroneAllopregnanolonePregnenoloneUlipristalSelective estrogenreceptor modulatorsRaloxifeneBazedoxifeneLasofoxifeneOrmeloxifeneOspemifenePrasterone