Estrogen - Wikipedia

Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex ... Estrogen FromWikipedia,thefreeencyclopedia Jumptonavigation Jumptosearch Primaryfemalesexhormone Thisarticleisaboutestrogensashormones.Fortheiruseasmedications,seeEstrogen(medication). EstrogenDrugclassEstradiol,themajorestrogensexhormoneinhumansandawidelyusedmedication.ClassidentifiersUseContraception,menopause,hypogonadism,transgenderwomen,prostatecancer,breastcancer,othersATCcodeG03CBiologicaltargetEstrogenreceptors(ERα,ERβ,mERs(e.g.,GPER,others))ExternallinksMeSHD004967InWikidata Estrogenoroestrogenisacategoryofsexhormoneresponsibleforthedevelopmentandregulationofthefemalereproductivesystemandsecondarysexcharacteristics.[1][2]Therearethreemajorendogenousestrogensthathaveestrogenichormonalactivity:estrone(E1),estradiol(E2),andestriol(E3).[1][3]Estradiol,anestrane,isthemostpotentandprevalent.[1]Anotherestrogencalledestetrol(E4)isproducedonlyduringpregnancy. Estrogensaresynthesizedinallvertebrates[4]andsomeinsects.[5]Theirpresenceinbothvertebratesandinsectssuggeststhatestrogenicsexhormoneshaveanancientevolutionaryhistory.Quantitatively,estrogenscirculateatlowerlevelsthanandrogensinbothmenandwomen.[6]Whileestrogenlevelsaresignificantlylowerinmalesthaninfemales,estrogensneverthelesshaveimportantphysiologicalrolesinmales.[7] Likeallsteroidhormones,estrogensreadilydiffuseacrossthecellmembrane.Onceinsidethecell,theybindtoandactivateestrogenreceptors(ERs)whichinturnmodulatetheexpressionofmanygenes.[8]Additionally,estrogensbindtoandactivaterapid-signalingmembraneestrogenreceptors(mERs),[9][10]suchasGPER(GPR30).[11] Inadditiontotheirroleasnaturalhormones,estrogensareusedasmedications,forinstanceinmenopausalhormonetherapy,hormonalbirthcontrolandfeminizinghormonetherapyfortransgenderwomenandnonbinarypeople. Contents 1Typesandexamples 2Biologicalfunction 2.1Overviewofactions 2.2Femalepubertaldevelopment 2.2.1Breastdevelopment 2.3Femalereproductivesystem 2.4NeuroprotectionandDNArepair 2.5Brainandbehavior 2.5.1Sexdrive 2.5.2Cognition 2.5.3Mentalhealth 2.5.4Parenthood 2.5.5Bingeeating 2.5.6Masculinizationinrodents 2.6Skeletalsystem 2.7Cardiovascularsystem 2.8Immunesystem 2.9Associatedconditions 3Biochemistry 3.1Biosynthesis 3.2Distribution 3.3Metabolism 3.4Excretion 4Medicaluse 5Chemistry 6History 7Societyandculture 7.1Etymology 7.2Environment 7.3Cosmetics 8Seealso 9References 10Externallinks Typesandexamples[edit] vteStructuresofmajorendogenousestrogens Estrone(E1) Estradiol(E2) Estriol(E3) Estetrol(E4) Notethehydroxyl(–OH)groups:estrone(E1)hasone,estradiol(E2)hastwo,estriol(E3)hasthree,andestetrol(E4)hasfour. Thefourmajornaturallyoccurringestrogensinwomenareestrone(E1),estradiol(E2),estriol(E3),andestetrol(E4).Estradiol(E2)isthepredominantestrogenduringreproductiveyearsbothintermsofabsoluteserumlevelsaswellasintermsofestrogenicactivity.Duringmenopause,estroneisthepredominantcirculatingestrogenandduringpregnancyestriolisthepredominantcirculatingestrogenintermsofserumlevels.Givenbysubcutaneousinjectioninmice,estradiolisabout10-foldmorepotentthanestroneandabout100-foldmorepotentthanestriol.[12]Thus,estradiolisthemostimportantestrogeninnon-pregnantfemaleswhoarebetweenthemenarcheandmenopausestagesoflife.However,duringpregnancythisroleshiftstoestriol,andinpostmenopausalwomenestronebecomestheprimaryformofestrogeninthebody.Anothertypeofestrogencalledestetrol(E4)isproducedonlyduringpregnancy.Allofthedifferentformsofestrogenaresynthesizedfromandrogens,specificallytestosteroneandandrostenedione,bytheenzymearomatase. Minorendogenousestrogens,thebiosynthesesofwhichdonotinvolvearomatase,include27-hydroxycholesterol,dehydroepiandrosterone(DHEA),7-oxo-DHEA,7α-hydroxy-DHEA,16α-hydroxy-DHEA,7β-hydroxyepiandrosterone,androstenedione(A4),androstenediol(A5),3α-androstanediol,and3β-androstanediol.[13][14]Someestrogenmetabolites,suchasthecatecholestrogens2-hydroxyestradiol,2-hydroxyestrone,4-hydroxyestradiol,and4-hydroxyestrone,aswellas16α-hydroxyestrone,arealsoestrogenswithvaryingdegreesofactivity.[15]Thebiologicalimportanceoftheseminorestrogensisnotentirelyclear. Biologicalfunction[edit] Referencerangesforthebloodcontentofestradiol,theprimarytypeofestrogen,duringthemenstrualcycle.[16] Theactionsofestrogenaremediatedbytheestrogenreceptor(ER),adimericnuclearproteinthatbindstoDNAandcontrolsgeneexpression.Likeothersteroidhormones,estrogenenterspassivelyintothecellwhereitbindstoandactivatestheestrogenreceptor.Theestrogen:ERcomplexbindstospecificDNAsequencescalledahormoneresponseelementtoactivatethetranscriptionoftargetgenes(inastudyusinganestrogen-dependentbreastcancercelllineasmodel,89suchgeneswereidentified).[17]Sinceestrogenentersallcells,itsactionsaredependentonthepresenceoftheERinthecell.TheERisexpressedinspecifictissuesincludingtheovary,uterusandbreast.ThemetaboliceffectsofestrogeninpostmenopausalwomenhavebeenlinkedtothegeneticpolymorphismoftheER.[18] Whileestrogensarepresentinbothmenandwomen,theyareusuallypresentatsignificantlyhigherlevelsinwomenofreproductiveage.Theypromotethedevelopmentoffemalesecondarysexualcharacteristics,suchasbreasts,andarealsoinvolvedinthethickeningoftheendometriumandotheraspectsofregulatingthemenstrualcycle.Inmales,estrogenregulatescertainfunctionsofthereproductivesystemimportanttothematurationofsperm[19][20][21]andmaybenecessaryforahealthylibido.[22] vteAffinitiesofestrogenreceptorligandsfortheERαandERβ Ligand Othernames Relativebindingaffinities(RBA, %)a Absolutebindingaffinities(Ki,nM)a Action ERα ERβ ERα ERβ Estradiol E2;17β-Estradiol 100 100 0.115(0.04–0.24) 0.15(0.10–2.08) Estrogen Estrone E1;17-Ketoestradiol 16.39(0.7–60) 6.5(1.36–52) 0.445(0.3–1.01) 1.75(0.35–9.24) Estrogen Estriol E3;16α-OH-17β-E2 12.65(4.03–56) 26(14.0–44.6) 0.45(0.35–1.4) 0.7(0.63–0.7) Estrogen Estetrol E4;15α,16α-Di-OH-17β-E2 4.0 3.0 4.9 19 Estrogen Alfatradiol 17α-Estradiol 20.5(7–80.1) 8.195(2–42) 0.2–0.52 0.43–1.2 Metabolite 16-Epiestriol 16β-Hydroxy-17β-estradiol 7.795(4.94–63) 50 ? ? Metabolite 17-Epiestriol 16α-Hydroxy-17α-estradiol 55.45(29–103) 79–80 ? ? Metabolite 16,17-Epiestriol 16β-Hydroxy-17α-estradiol 1.0 13 ? ? Metabolite 2-Hydroxyestradiol 2-OH-E2 22(7–81) 11–35 2.5 1.3 Metabolite 2-Methoxyestradiol 2-MeO-E2 0.0027–2.0 1.0 ? ? Metabolite 4-Hydroxyestradiol 4-OH-E2 13(8–70) 7–56 1.0 1.9 Metabolite 4-Methoxyestradiol 4-MeO-E2 2.0 1.0 ? ? Metabolite 2-Hydroxyestrone 2-OH-E1 2.0–4.0 0.2–0.4 ? ? Metabolite 2-Methoxyestrone 2-MeO-E1 <0.001–<1 <1 ? ? Metabolite 4-Hydroxyestrone 4-OH-E1 1.0–2.0 1.0 ? ? Metabolite 4-Methoxyestrone 4-MeO-E1 <1 <1 ? ? Metabolite 16α-Hydroxyestrone 16α-OH-E1;17-Ketoestriol 2.0–6.5 35 ? ? Metabolite 2-Hydroxyestriol 2-OH-E3 2.0 1.0 ? ? Metabolite 4-Methoxyestriol 4-MeO-E3 1.0 1.0 ? ? Metabolite Estradiolsulfate E2S;Estradiol3-sulfate <1 <1 ? ? Metabolite Estradioldisulfate Estradiol3,17β-disulfate 0.0004 ? ? ? Metabolite Estradiol3-glucuronide E2-3G 0.0079 ? ? ? Metabolite Estradiol17β-glucuronide E2-17G 0.0015 ? ? ? Metabolite Estradiol3-gluc.17β-sulfate E2-3G-17S 0.0001 ? ? ? Metabolite Estronesulfate E1S;Estrone3-sulfate <1 <1 >10 >10 Metabolite Estradiolbenzoate EB;Estradiol3-benzoate 10 ? ? ? Estrogen Estradiol17β-benzoate E2-17B 11.3 32.6 ? ? Estrogen Estronemethylether Estrone3-methylether 0.145 ? ? ? Estrogen ent-Estradiol 1-Estradiol 1.31–12.34 9.44–80.07 ? ? Estrogen Equilin 7-Dehydroestrone 13(4.0–28.9) 13.0–49 0.79 0.36 Estrogen Equilenin 6,8-Didehydroestrone 2.0–15 7.0–20 0.64 0.62 Estrogen 17β-Dihydroequilin 7-Dehydro-17β-estradiol 7.9–113 7.9–108 0.09 0.17 Estrogen 17α-Dihydroequilin 7-Dehydro-17α-estradiol 18.6(18–41) 14–32 0.24 0.57 Estrogen 17β-Dihydroequilenin 6,8-Didehydro-17β-estradiol 35–68 90–100 0.15 0.20 Estrogen 17α-Dihydroequilenin 6,8-Didehydro-17α-estradiol 20 49 0.50 0.37 Estrogen Δ8-Estradiol 8,9-Dehydro-17β-estradiol 68 72 0.15 0.25 Estrogen Δ8-Estrone 8,9-Dehydroestrone 19 32 0.52 0.57 Estrogen Ethinylestradiol EE;17α-Ethynyl-17β-E2 120.9(68.8–480) 44.4(2.0–144) 0.02–0.05 0.29–0.81 Estrogen Mestranol EE3-methylether ? 2.5 ? ? Estrogen Moxestrol RU-2858;11β-Methoxy-EE 35–43 5–20 0.5 2.6 Estrogen Methylestradiol 17α-Methyl-17β-estradiol 70 44 ? ? Estrogen Diethylstilbestrol DES;Stilbestrol 129.5(89.1–468) 219.63(61.2–295) 0.04 0.05 Estrogen Hexestrol Dihydrodiethylstilbestrol 153.6(31–302) 60–234 0.06 0.06 Estrogen Dienestrol Dehydrostilbestrol 37(20.4–223) 56–404 0.05 0.03 Estrogen Benzestrol(B2) – 114 ? ? ? Estrogen Chlorotrianisene TACE 1.74 ? 15.30 ? Estrogen Triphenylethylene TPE 0.074 ? ? ? Estrogen Triphenylbromoethylene TPBE 2.69 ? ? ? Estrogen Tamoxifen ICI-46,474 3(0.1–47) 3.33(0.28–6) 3.4–9.69 2.5 SERM Afimoxifene 4-Hydroxytamoxifen;4-OHT 100.1(1.7–257) 10(0.98–339) 2.3(0.1–3.61) 0.04–4.8 SERM Toremifene 4-Chlorotamoxifen;4-CT ? ? 7.14–20.3 15.4 SERM Clomifene MRL-41 25(19.2–37.2) 12 0.9 1.2 SERM Cyclofenil F-6066;Sexovid 151–152 243 ? ? SERM Nafoxidine U-11,000A 30.9–44 16 0.3 0.8 SERM Raloxifene – 41.2(7.8–69) 5.34(0.54–16) 0.188–0.52 20.2 SERM Arzoxifene LY-353,381 ? ? 0.179 ? SERM Lasofoxifene CP-336,156 10.2–166 19.0 0.229 ? SERM Ormeloxifene Centchroman ? ? 0.313 ? SERM Levormeloxifene 6720-CDRI;NNC-460,020 1.55 1.88 ? ? SERM Ospemifene Deaminohydroxytoremifene 0.82–2.63 0.59–1.22 ? ? SERM Bazedoxifene – ? ? 0.053 ? SERM Etacstil GW-5638 4.30 11.5 ? ? SERM ICI-164,384 – 63.5(3.70–97.7) 166 0.2 0.08 Antiestrogen Fulvestrant ICI-182,780 43.5(9.4–325) 21.65(2.05–40.5) 0.42 1.3 Antiestrogen Propylpyrazoletriol PPT 49(10.0–89.1) 0.12 0.40 92.8 ERαagonist 16α-LE2 16α-Lactone-17β-estradiol 14.6–57 0.089 0.27 131 ERαagonist 16α-Iodo-E2 16α-Iodo-17β-estradiol 30.2 2.30 ? ? ERαagonist Methylpiperidinopyrazole MPP 11 0.05 ? ? ERαantagonist Diarylpropionitrile DPN 0.12–0.25 6.6–18 32.4 1.7 ERβagonist 8β-VE2 8β-Vinyl-17β-estradiol 0.35 22.0–83 12.9 0.50 ERβagonist Prinaberel ERB-041;WAY-202,041 0.27 67–72 ? ? ERβagonist ERB-196 WAY-202,196 ? 180 ? ? ERβagonist Erteberel SERBA-1;LY-500,307 ? ? 2.68 0.19 ERβagonist SERBA-2 – ? ? 14.5 1.54 ERβagonist Coumestrol – 9.225(0.0117–94) 64.125(0.41–185) 0.14–80.0 0.07–27.0 Xenoestrogen Genistein – 0.445(0.0012–16) 33.42(0.86–87) 2.6–126 0.3–12.8 Xenoestrogen Equol – 0.2–0.287 0.85(0.10–2.85) ? ? Xenoestrogen Daidzein – 0.07(0.0018–9.3) 0.7865(0.04–17.1) 2.0 85.3 Xenoestrogen BiochaninA – 0.04(0.022–0.15) 0.6225(0.010–1.2) 174 8.9 Xenoestrogen Kaempferol – 0.07(0.029–0.10) 2.2(0.002–3.00) ? ? Xenoestrogen Naringenin – 0.0054(<0.001–0.01) 0.15(0.11–0.33) ? ? Xenoestrogen 8-Prenylnaringenin 8-PN 4.4 ? ? ? Xenoestrogen Quercetin – <0.001–0.01 0.002–0.040 ? ? Xenoestrogen Ipriflavone – <0.01 <0.01 ? ? Xenoestrogen Miroestrol – 0.39 ? ? ? Xenoestrogen Deoxymiroestrol – 2.0 ? ? ? Xenoestrogen β-Sitosterol – <0.001–0.0875 <0.001–0.016 ? ? Xenoestrogen Resveratrol – <0.001–0.0032 ? ? ? Xenoestrogen α-Zearalenol – 48(13–52.5) ? ? ? Xenoestrogen β-Zearalenol – 0.6(0.032–13) ? ? ? Xenoestrogen Zeranol α-Zearalanol 48–111 ? ? ? Xenoestrogen Taleranol β-Zearalanol 16(13–17.8) 14 0.8 0.9 Xenoestrogen Zearalenone ZEN 7.68(2.04–28) 9.45(2.43–31.5) ? ? Xenoestrogen Zearalanone ZAN 0.51 ? ? ? Xenoestrogen BisphenolA BPA 0.0315(0.008–1.0) 0.135(0.002–4.23) 195 35 Xenoestrogen Endosulfan EDS <0.001–<0.01 <0.01 ? ? Xenoestrogen Kepone Chlordecone 0.0069–0.2 ? ? ? Xenoestrogen o,p'-DDT – 0.0073–0.4 ? ? ? Xenoestrogen p,p'-DDT – 0.03 ? ? ? Xenoestrogen Methoxychlor p,p'-Dimethoxy-DDT 0.01(<0.001–0.02) 0.01–0.13 ? ? Xenoestrogen HPTE Hydroxychlor;p,p'-OH-DDT 1.2–1.7 ? ? ? Xenoestrogen Testosterone T;4-Androstenolone <0.0001–<0.01 <0.002–0.040 >5000 >5000 Androgen Dihydrotestosterone DHT;5α-Androstanolone 0.01(<0.001–0.05) 0.0059–0.17 221–>5000 73–1688 Androgen Nandrolone 19-Nortestosterone;19-NT 0.01 0.23 765 53 Androgen Dehydroepiandrosterone DHEA;Prasterone 0.038(<0.001–0.04) 0.019–0.07 245–1053 163–515 Androgen 5-Androstenediol A5;Androstenediol 6 17 3.6 0.9 Androgen 4-Androstenediol – 0.5 0.6 23 19 Androgen 4-Androstenedione A4;Androstenedione <0.01 <0.01 >10000 >10000 Androgen 3α-Androstanediol 3α-Adiol 0.07 0.3 260 48 Androgen 3β-Androstanediol 3β-Adiol 3 7 6 2 Androgen Androstanedione 5α-Androstanedione <0.01 <0.01 >10000 >10000 Androgen Etiocholanedione 5β-Androstanedione <0.01 <0.01 >10000 >10000 Androgen Methyltestosterone 17α-Methyltestosterone <0.0001 ? ? ? Androgen Ethinyl-3α-androstanediol 17α-Ethynyl-3α-adiol 4.0 <0.07 ? ? Estrogen Ethinyl-3β-androstanediol 17α-Ethynyl-3β-adiol 50 5.6 ? ? Estrogen Progesterone P4;4-Pregnenedione <0.001–0.6 <0.001–0.010 ? ? Progestogen Norethisterone NET;17α-Ethynyl-19-NT 0.085(0.0015–<0.1) 0.1(0.01–0.3) 152 1084 Progestogen Norethynodrel 5(10)-Norethisterone 0.5(0.3–0.7) <0.1–0.22 14 53 Progestogen Tibolone 7α-Methylnorethynodrel 0.5(0.45–2.0) 0.2–0.076 ? ? Progestogen Δ4-Tibolone 7α-Methylnorethisterone 0.069–<0.1 0.027–<0.1 ? ? Progestogen 3α-Hydroxytibolone – 2.5(1.06–5.0) 0.6–0.8 ? ? Progestogen 3β-Hydroxytibolone – 1.6(0.75–1.9) 0.070–0.1 ? ? Progestogen Footnotes:a=(1)Bindingaffinityvaluesareoftheformat"median(range)"(#(#–#)),"range"(#–#),or"value"(#)dependingonthevaluesavailable.ThefullsetsofvalueswithintherangescanbefoundintheWikicode.(2)Bindingaffinitiesweredeterminedviadisplacementstudiesinavarietyofin-vitrosystemswithlabeledestradiolandhumanERαandERβproteins(excepttheERβvaluesfromKuiperetal.(1997),whichareratERβ).Sources:Seetemplatepage. vteRelativeaffinitiesofestrogensforsteroidhormonereceptorsandbloodproteins Estrogen Relativebindingaffinities(%) ER AR PR GR MR SHBG CBG Estradiol 100 7.9 2.6 0.6 0.13 8.7–12 <0.1 Estradiolbenzoate ? ? ? ? ? <0.1–0.16 <0.1 Estradiolvalerate 2 ? ? ? ? ? ? Estrone 11–35 <1 <1 <1 <1 2.7 <0.1 Estronesulfate 2 2 ? ? ? ? ? Estriol 10–15 <1 <1 <1 <1 <0.1 <0.1 Equilin 40 ? ? ? ? ? 0 Alfatradiol 15 <1 <1 <1 <1 ? ? Epiestriol 20 <1 <1 <1 <1 ? ? Ethinylestradiol 100–112 1–3 15–25 1–3 <1 0.18 <0.1 Mestranol 1 ? ? ? ? <0.1 <0.1 Methylestradiol 67 1–3 3–25 1–3 <1 ? ? Moxestrol 12 <0.1 0.8 3.2 <0.1 <0.2 <0.1 Diethylstilbestrol ? ? ? ? ? <0.1 <0.1 Notes:Referenceligands(100%)wereprogesteroneforthePR,testosteronefortheAR,estradiolfortheER,dexamethasonefortheGR,aldosteronefortheMR,dihydrotestosteroneforSHBG,andcortisolforCBG.Sources:Seetemplate. vteAffinitiesandestrogenicpotenciesofestrogenestersandethersattheestrogenreceptors Estrogen Othernames RBA(%)a REP(%)b ER ERα ERβ Estradiol E2 100 100 100 Estradiol3-sulfate E2S;E2-3S ? 0.02 0.04 Estradiol3-glucuronide E2-3G ? 0.02 0.09 Estradiol17β-glucuronide E2-17G ? 0.002 0.0002 Estradiolbenzoate EB;Estradiol3-benzoate 10 1.1 0.52 Estradiol17β-acetate E2-17A 31–45 24 ? Estradioldiacetate EDA;Estradiol3,17β-diacetate ? 0.79 ? Estradiolpropionate EP;Estradiol17β-propionate 19–26 2.6 ? Estradiolvalerate EV;Estradiol17β-valerate 2–11 0.04–21 ? Estradiolcypionate EC;Estradiol17β-cypionate ?c 4.0 ? Estradiolpalmitate Estradiol17β-palmitate 0 ? ? Estradiolstearate Estradiol17β-stearate 0 ? ? Estrone E1;17-Ketoestradiol 11 5.3–38 14 Estronesulfate E1S;Estrone3-sulfate 2 0.004 0.002 Estroneglucuronide E1G;Estrone3-glucuronide ? <0.001 0.0006 Ethinylestradiol EE;17α-Ethynylestradiol 100 17–150 129 Mestranol EE3-methylether 1 1.3–8.2 0.16 Quinestrol EE3-cyclopentylether ? 0.37 ? Footnotes:a=Relativebindingaffinities(RBAs)weredeterminedviain-vitrodisplacementoflabeledestradiolfromestrogenreceptors(ERs)generallyofrodentuterinecytosol.Estrogenestersarevariablyhydrolyzedintoestrogensinthesesystems(shorteresterchainlength->greaterrateofhydrolysis)andtheERRBAsoftheestersdecreasestronglywhenhydrolysisisprevented.b=Relativeestrogenicpotencies(REPs)werecalculatedfromhalf-maximaleffectiveconcentrations(EC50)thatweredeterminedviain-vitroβ‐galactosidase(β-gal)andgreenfluorescentprotein(GFP)productionassaysinyeastexpressinghumanERαandhumanERβ.Bothmammaliancellsandyeasthavethecapacitytohydrolyzeestrogenesters.c=TheaffinitiesofestradiolcypionatefortheERsaresimilartothoseofestradiolvalerateandestradiolbenzoate(figure).Sources:Seetemplatepage. vteSelectedbiologicalpropertiesofendogenousestrogensinrats Estrogen ERRBA(%) Uterineweight(%) Uterotrophy LHlevels(%) SHBGRBA(%) Control – 100 – 100 – Estradiol(E2) 100 506±20 +++ 12–19 100 Estrone(E1) 11±8 490±22 +++ ? 20 Estriol(E3) 10±4 468±30 +++ 8–18 3 Estetrol(E4) 0.5±0.2 ? Inactive ? 1 17α-Estradiol 4.2±0.8 ? ? ? ? 2-Hydroxyestradiol 24±7 285±8 +b 31–61 28 2-Methoxyestradiol 0.05±0.04 101 Inactive ? 130 4-Hydroxyestradiol 45±12 ? ? ? ? 4-Methoxyestradiol 1.3±0.2 260 ++ ? 9 4-Fluoroestradiola 180±43 ? +++ ? ? 2-Hydroxyestrone 1.9±0.8 130±9 Inactive 110–142 8 2-Methoxyestrone 0.01±0.00 103±7 Inactive 95–100 120 4-Hydroxyestrone 11±4 351 ++ 21–50 35 4-Methoxyestrone 0.13±0.04 338 ++ 65–92 12 16α-Hydroxyestrone 2.8±1.0 552±42 +++ 7–24 <0.5 2-Hydroxyestriol 0.9±0.3 302 +b ? ? 2-Methoxyestriol 0.01±0.00 ? Inactive ? 4 Notes:Valuesaremean±SDorrange.ERRBA=Relativebindingaffinitytoestrogenreceptorsofratuterinecytosol.Uterineweight=Percentagechangeinuterinewetweightofovariectomizedratsafter72 hourswithcontinuousadministrationof1 μg/hourviasubcutaneouslyimplantedosmoticpumps.LHlevels=Luteinizinghormonelevelsrelativetobaselineofovariectomizedratsafter24to72 hoursofcontinuousadministrationviasubcutaneousimplant.Footnotes:a=Synthetic(i.e.,notendogenous).b=Atypicaluterotrophiceffectwhichplateauswithin48 hours(estradiol'suterotrophycontinueslinearlyupto72 hours).Sources:Seetemplate. Overviewofactions[edit] Thissectionisinlistformatbutmayreadbetterasprose.Youcanhelpbyconvertingthissection,ifappropriate.Editinghelpisavailable.(October2019) Structural Anabolic:Increasesmusclemassandstrength,speedofmuscleregeneration,andbonedensity,increasedsensitivitytoexercise,protectionagainstmuscledamage,strongercollagensynthesis,increasesthecollagencontentofconnectivetissues,tendons,andligaments,butalsodecreasesstiffnessoftendonsandligaments(especiallyduringmenstruation).Decreasedstiffnessoftendonsgiveswomenmuchlowerpredispositiontomusclestrainsbutsoftligamentsaremuchmorepronetoinjuries(ACLtearsare2-8xmorecommonamongwomenthanmen).[23][24][25][26] Anti-inflammatoryproperties Mediateformationoffemalesecondarysexcharacteristics Acceleratemetabolism Increasedfatstorageinsomebodypartssuchasbreasts,buttocks,andlegsbutdecreasedabdominalandvisceralfat(androgenicobesity).[27][28][29]Estradiolalsoregulatesenergyexpenditure,bodyweighthomeostasis,andseemstohavemuchstrongeranti-obesityeffectsthantestosteroneingeneral.[30] Womentendtohavelowerbasestrengthbutonaveragehaveaboutthesameincreasesofmusclemassinresponsestoresistancetrainingasmenandfarfasterrelativeincreasesinstrength.[31][32] Stimulateendometrialgrowth Increaseuterinegrowth Increasevaginallubrication Thickenthevaginalwall Maintenanceofvesselandskin Reduceboneresorption,increaseboneformation Proteinsynthesis Increasehepaticproductionofbindingproteins Coagulation Increasecirculatingleveloffactors2,7,9,10,plasminogen DecreaseantithrombinIII Increaseplateletadhesiveness IncreasevWF(estrogen->AngiotensinII->Vasopressin) IncreasePAI-1andPAI-2alsothroughAngiotensinII Lipid IncreaseHDL,triglyceride DecreaseLDL,fatdeposition Fluidbalance Salt(sodium)andwaterretention Increasecortisol,SHBG Gastrointestinaltract Reducebowelmotility Increasecholesterolinbile Melanin Increasepheomelanin,reduceeumelanin Cancer Supporthormone-sensitivebreastcancers(seesectionbelow) Lungfunction Promoteslungfunctionbysupportingalveoli(inrodentsbutprobablyinhumans).[33] Uteruslining Estrogentogetherwithprogesteronepromotesandmaintainstheuteruslininginpreparationforimplantationoffertilizedeggandmaintenanceofuterusfunctionduringgestationperiod,alsoupregulatesoxytocinreceptorinmyometrium Ovulation Surgeinestrogenlevelinducesthereleaseofluteinizinghormone,whichthentriggersovulationbyreleasingtheeggfromtheGraafianfollicleintheovary. Sexualbehavior Estrogenisrequiredforfemalemammalstoengageinlordosisbehaviorduringestrus(whenanimalsare"inheat").[34][35]Thisbehaviorisrequiredforsexualreceptivityinthesemammalsandisregulatedbytheventromedialnucleusofthehypothalamus.[36] Sexdriveisdependentonandrogenlevels[37]onlyinthepresenceofestrogen,butwithoutestrogen,freetestosteronelevelactuallydecreasessexualdesire(insteadofincreasessexdrive),asdemonstratedforthosewomenwhohavehypoactivesexualdesiredisorder,andthesexualdesireinthesewomencanberestoredbyadministrationofestrogen(usingoralcontraceptive).[38] Femalepubertaldevelopment[edit] Estrogensareresponsibleforthedevelopmentoffemalesecondarysexualcharacteristicsduringpuberty,includingbreastdevelopment,wideningofthehips,andfemalefatdistribution.Conversely,androgensareresponsibleforpubicandbodyhairgrowth,aswellasacneandaxillaryodor. Breastdevelopment[edit] Seealso:Breastdevelopment§ Biochemistry Estrogen,inconjunctionwithgrowthhormone(GH)anditssecretoryproductinsulin-likegrowthfactor1(IGF-1),iscriticalinmediatingbreastdevelopmentduringpuberty,aswellasbreastmaturationduringpregnancyinpreparationoflactationandbreastfeeding.[39][40]Estrogenisprimarilyanddirectlyresponsibleforinducingtheductalcomponentofbreastdevelopment,[41][42][43]aswellasforcausingfatdepositionandconnectivetissuegrowth.[41][42]Itisalsoindirectlyinvolvedinthelobuloalveolarcomponent,byincreasingprogesteronereceptorexpressioninthebreasts[41][43][44]andbyinducingthesecretionofprolactin.[45][46]Allowedforbyestrogen,progesteroneandprolactinworktogethertocompletelobuloalveolardevelopmentduringpregnancy.[42][47] Androgenssuchastestosteronepowerfullyopposeestrogenactioninthebreasts,suchasbyreducingestrogenreceptorexpressioninthem.[48][49] Femalereproductivesystem[edit] Estrogensareresponsibleformaturationandmaintenanceofthevaginaanduterus,andarealsoinvolvedinovarianfunction,suchasmaturationofovarianfollicles.Inaddition,estrogensplayanimportantroleinregulationofgonadotropinsecretion.Forthesereasons,estrogensarerequiredforfemalefertility. NeuroprotectionandDNArepair[edit] EstrogenregulatedDNArepairmechanismsinthebrainhaveneuroprotectiveeffects.[50]EstrogenregulatesthetranscriptionofDNAbaseexcisionrepairgenesaswellasthetranslocationofthebaseexcisionrepairenzymesbetweendifferentsubcellularcompartments. Brainandbehavior[edit] Sexdrive[edit] Seealso:Sexualmotivationandhormones Estrogensareinvolvedinlibido(sexdrive)inbothwomenandmen. Cognition[edit] Verbalmemoryscoresarefrequentlyusedasonemeasureofhigherlevelcognition.Thesescoresvaryindirectproportiontoestrogenlevelsthroughoutthemenstrualcycle,pregnancy,andmenopause.Furthermore,estrogenswhenadministeredshortlyafternaturalorsurgicalmenopausepreventsdecreasesinverbalmemory.Incontrast,estrogenshavelittleeffectonverbalmemoryiffirstadministeredyearsaftermenopause.[51]Estrogensalsohavepositiveinfluencesonothermeasuresofcognitivefunction.[52]Howevertheeffectofestrogensoncognitionisnotuniformlyfavorableandisdependentonthetimingofthedoseandthetypeofcognitiveskillbeingmeasured.[53] Theprotectiveeffectsofestrogensoncognitionmaybemediatedbyestrogen'santi-inflammatoryeffectsinthebrain.[54]StudieshavealsoshownthattheMetallelegeneandlevelofestrogenmediatestheefficiencyofprefrontalcortexdependentworkingmemorytasks.[55][56]Researchershaveurgedforfurtherresearchtoilluminatetheroleofestrogenanditspotentialforimprovementoncognitivefunction.[57] Mentalhealth[edit] Estrogenisconsideredtoplayasignificantroleinwomen'smentalhealth.Suddenestrogenwithdrawal,fluctuatingestrogen,andperiodsofsustainedlowestrogenlevelscorrelatewithsignificantmoodlowering.Clinicalrecoveryfrompostpartum,perimenopause,andpostmenopausedepressionhasbeenshowntobeeffectiveafterlevelsofestrogenwerestabilizedand/orrestored.[58][59][60]Menstrualexacerbation(includingmenstrualpsychosis)istypicallytriggeredbylowestrogenlevels,[61]andisoftenmistakenforpremenstrualdysphoricdisorder.[62] Compulsionsinmalelabmice,suchasthoseinobsessive-compulsivedisorder(OCD),maybecausedbylowestrogenlevels.Whenestrogenlevelswereraisedthroughtheincreasedactivityoftheenzymearomataseinmalelabmice,OCDritualsweredramaticallydecreased.HypothalamicproteinlevelsinthegeneCOMTareenhancedbyincreasingestrogenlevelswhicharebelievedtoreturnmicethatdisplayedOCDritualstonormalactivity.Aromatasedeficiencyisultimatelysuspectedwhichisinvolvedinthesynthesisofestrogeninhumansandhastherapeuticimplicationsinhumanshavingobsessive-compulsivedisorder.[63] Localapplicationofestrogenintherathippocampushasbeenshowntoinhibitthere-uptakeofserotonin.Contrarily,localapplicationofestrogenhasbeenshowntoblocktheabilityoffluvoxaminetoslowserotoninclearance,suggestingthatthesamepathwayswhichareinvolvedinSSRIefficacymayalsobeaffectedbycomponentsoflocalestrogensignalingpathways.[64] Parenthood[edit] Studieshavealsofoundthatfathershadlowerlevelsofcortisolandtestosteronebuthigherlevelsofestrogen(estradiol)thandidnon-fathers.[65] Bingeeating[edit] Estrogenmayplayaroleinsuppressingbingeeating.Hormonereplacementtherapyusingestrogenmaybeapossibletreatmentforbingeeatingbehaviorsinfemales.Estrogenreplacementhasbeenshowntosuppressbingeeatingbehaviorsinfemalemice.[66]Themechanismbywhichestrogenreplacementinhibitsbinge-likeeatinginvolvesthereplacementofserotonin(5-HT)neurons.Womenexhibitingbingeeatingbehaviorsarefoundtohaveincreasedbrainuptakeofneuron5-HT,andthereforelessoftheneurotransmitterserotonininthecerebrospinalfluid.[67]Estrogenworkstoactivate5-HTneurons,leadingtosuppressionofbingelikeeatingbehaviors.[66] Itisalsosuggestedthatthereisaninteractionbetweenhormonelevelsandeatingatdifferentpointsinthefemalemenstrualcycle.Researchhaspredictedincreasedemotionaleatingduringhormonalflux,whichischaracterizedbyhighprogesteroneandestradiollevelsthatoccurduringthemid-lutealphase.Itishypothesizedthatthesechangesoccurduetobrainchangesacrossthemenstrualcyclethatarelikelyagenomiceffectofhormones.Theseeffectsproducemenstrualcyclechanges,whichresultinhormonereleaseleadingtobehavioralchanges,notablybingeandemotionaleating.Theseoccurespeciallyprominentlyamongwomenwhoaregeneticallyvulnerabletobingeeatingphenotypes.[68] Bingeeatingisassociatedwithdecreasedestradiolandincreasedprogesterone.[69]Klumpetal.[70]Progesteronemaymoderatetheeffectsoflowestradiol(suchasduringdysregulatedeatingbehavior),butthatthismayonlybetrueinwomenwhohavehadclinicallydiagnosedbingeepisodes(BEs).DysregulatedeatingismorestronglyassociatedwithsuchovarianhormonesinwomenwithBEsthaninwomenwithoutBEs.[70] Theimplantationof17β-estradiolpelletsinovariectomizedmicesignificantlyreducedbingeeatingbehaviorsandinjectionsofGLP-1inovariectomizedmicedecreasedbinge-eatingbehaviors.[66] Theassociationsbetweenbingeeating,menstrual-cyclephaseandovarianhormonescorrelated.[69][71][72] Masculinizationinrodents[edit] Inrodents,estrogens(whicharelocallyaromatizedfromandrogensinthebrain)playanimportantroleinpsychosexualdifferentiation,forexample,bymasculinizingterritorialbehavior;[73]thesameisnottrueinhumans.[74]Inhumans,themasculinizingeffectsofprenatalandrogensonbehavior(andothertissues,withthepossibleexceptionofeffectsonbone)appeartoactexclusivelythroughtheandrogenreceptor.[75]Consequently,theutilityofrodentmodelsforstudyinghumanpsychosexualdifferentiationhasbeenquestioned.[76] Skeletalsystem[edit] Estrogensareresponsibleforboththepubertalgrowthspurt,whichcausesanaccelerationinlineargrowth,andepiphysealclosure,whichlimitsheightandlimblength,inbothfemalesandmales.Inaddition,estrogensareresponsibleforbonematurationandmaintenanceofbonemineraldensitythroughoutlife.Duetohypoestrogenism,theriskofosteoporosisincreasesduringmenopause. Cardiovascularsystem[edit] Womensufferlessfromheartdiseaseduetovasculo-protectiveactionofestrogenwhichhelpsinpreventingatherosclerosis.[77]Italsohelpsinmaintainingthedelicatebalancebetweenfightinginfectionsandprotectingarteriesfromdamagethusloweringtheriskofcardiovasculardisease.[78]Duringpregnancy,highlevelsofestrogensincreasecoagulationandtheriskofvenousthromboembolism. vteAbsoluteandrelativeincidenceofvenousthromboembolism(VTE)duringpregnancyandthepostpartumperiod AbsoluteincidenceoffirstVTEper10,000person–yearsduringpregnancyandthepostpartumperiod SwedishdataA SwedishdataB Englishdata Danishdata Timeperiod N Rate(95%CI) N Rate(95%CI) N Rate(95%CI) N Rate(95%CI) Outsidepregnancy 1105 4.2(4.0–4.4) 1015 3.8(?) 1480 3.2(3.0–3.3) 2895 3.6(3.4–3.7) Antepartum 995 20.5(19.2–21.8) 690 14.2(13.2–15.3) 156 9.9(8.5–11.6) 491 10.7(9.7–11.6)   Trimester1 207 13.6(11.8–15.5) 172 11.3(9.7–13.1) 23 4.6(3.1–7.0) 61 4.1(3.2–5.2)   Trimester2 275 17.4(15.4–19.6) 178 11.2(9.7–13.0) 30 5.8(4.1–8.3) 75 5.7(4.6–7.2)   Trimester3 513 29.2(26.8–31.9) 340 19.4(17.4–21.6) 103 18.2(15.0–22.1) 355 19.7(17.7–21.9) Arounddelivery 115 154.6(128.8–185.6) 79 106.1(85.1–132.3) 34 142.8(102.0–199.8) – Postpartum 649 42.3(39.2–45.7) 509 33.1(30.4–36.1) 135 27.4(23.1–32.4) 218 17.5(15.3–20.0)   Earlypostpartum 584 75.4(69.6–81.8) 460 59.3(54.1–65.0) 177 46.8(39.1–56.1) 199 30.4(26.4–35.0)   Latepostpartum 65 8.5(7.0–10.9) 49 6.4(4.9–8.5) 18 7.3(4.6–11.6) 319 3.2(1.9–5.0) Incidencerateratios(IRRs)offirstVTEduringpregnancyandthepostpartumperiod SwedishdataA SwedishdataB Englishdata Danishdata Timeperiod IRR*(95%CI) IRR*(95%CI) IRR(95%CI)† IRR(95%CI)† Outsidepregnancy Reference(i.e.,1.00) Antepartum 5.08(4.66–5.54) 3.80(3.44–4.19) 3.10(2.63–3.66) 2.95(2.68–3.25)   Trimester1 3.42(2.95–3.98) 3.04(2.58–3.56) 1.46(0.96–2.20) 1.12(0.86–1.45)   Trimester2 4.31(3.78–4.93) 3.01(2.56–3.53) 1.82(1.27–2.62) 1.58(1.24–1.99)   Trimester3 7.14(6.43–7.94) 5.12(4.53–5.80) 5.69(4.66–6.95) 5.48(4.89–6.12) Arounddelivery 37.5(30.9–44.45) 27.97(22.24–35.17) 44.5(31.68–62.54) – Postpartum 10.21(9.27–11.25) 8.72(7.83–9.70) 8.54(7.16–10.19) 4.85(4.21–5.57)   Earlypostpartum 19.27(16.53–20.21) 15.62(14.00–17.45) 14.61(12.10–17.67) 8.44(7.27–9.75)   Latepostpartum 2.06(1.60–2.64) 1.69(1.26–2.25) 2.29(1.44–3.65) 0.89(0.53–1.39) Notes:SwedishdataA=UsinganycodeforVTEregardlessofconfirmation.SwedishdataB=Usingonlyalgorithm-confirmedVTE.Earlypostpartum=First6weeksafterdelivery.Latepostpartum=Morethan6weeksafterdelivery.*=Adjustedforageandcalendaryear.†=Unadjustedratiocalculatedbasedonthedataprovided.Source:[79] Immunesystem[edit] Estrogenhasanti-inflammatorypropertiesandhelpsinmobilizationofpolymorphonuclearwhitebloodcellsorneutrophils.[78] Associatedconditions[edit] Researchershaveimplicatedestrogensinvariousestrogen-dependentconditions,suchasER-positivebreastcancer,aswellasanumberofgeneticconditionsinvolvingestrogensignalingormetabolism,suchasestrogeninsensitivitysyndrome,aromatasedeficiency,andaromataseexcesssyndrome. Highestrogencanamplifystress-hormoneresponsesinstressfulsituations.[80] Biochemistry[edit] Seealso:Estradiol§ Biochemistry Biosynthesis[edit] Steroidogenesis,showingestrogensatbottomrightasinpinktriangle.[81] Estrogens,infemales,areproducedprimarilybytheovaries,andduringpregnancy,theplacenta.[82]Follicle-stimulatinghormone(FSH)stimulatestheovarianproductionofestrogensbythegranulosacellsoftheovarianfolliclesandcorporalutea.Someestrogensarealsoproducedinsmalleramountsbyothertissuessuchastheliver,pancreas,bone,adrenalglands,skin,brain,adiposetissue,[83]andthebreasts.[84]Thesesecondarysourcesofestrogensareespeciallyimportantinpostmenopausalwomen.[85] Thepathwayofestrogenbiosynthesisinextragonadaltissuesisdifferent.ThesetissuesarenotabletosynthesizeC19steroids,andthereforedependonC19suppliesfromothertissues[85]andthelevelofaromatase.[86] Infemales,synthesisofestrogensstartsinthecainternacellsintheovary,bythesynthesisofandrostenedionefromcholesterol.Androstenedioneisasubstanceofweakandrogenicactivitywhichservespredominantlyasaprecursorformorepotentandrogenssuchastestosteroneaswellasestrogen.Thiscompoundcrossesthebasalmembraneintothesurroundinggranulosacells,whereitisconvertedeitherimmediatelyintoestrone,orintotestosteroneandthenestradiolinanadditionalstep.Theconversionofandrostenedionetotestosteroneiscatalyzedby17β-hydroxysteroiddehydrogenase(17β-HSD),whereastheconversionofandrostenedioneandtestosteroneintoestroneandestradiol,respectivelyiscatalyzedbyaromatase,enzymeswhicharebothexpressedingranulosacells.Incontrast,granulosacellslack17α-hydroxylaseand17,20-lyase,whereasthecacellsexpresstheseenzymesand17β-HSDbutlackaromatase.Hence,bothgranulosaandthecacellsareessentialfortheproductionofestrogenintheovaries. Estrogenlevelsvarythroughthemenstrualcycle,withlevelshighestneartheendofthefollicularphasejustbeforeovulation. Notethatinmales,estrogenisalsoproducedbytheSertolicellswhenFSHbindstotheirFSHreceptors. vteProductionrates,secretionrates,clearancerates,andbloodlevelsofmajorsexhormones Sex Sexhormone Reproductivephase Bloodproductionrate Gonadalsecretionrate Metabolicclearancerate Referencerange(serumlevels) SIunits Non-SIunits Men Androstenedione – 2.8mg/day 1.6mg/day 2200L/day 2.8–7.3nmol/L 80–210ng/dL Testosterone – 6.5mg/day 6.2mg/day 950L/day 6.9–34.7nmol/L 200–1000ng/dL Estrone – 150μg/day 110μg/day 2050L/day 37–250pmol/L 10–70pg/mL Estradiol – 60μg/day 50μg/day 1600L/day <37–210pmol/L 10–57pg/mL Estronesulfate – 80μg/day Insignificant 167L/day 600–2500pmol/L 200–900pg/mL Women Androstenedione – 3.2mg/day 2.8mg/day 2000L/day 3.1–12.2nmol/L 89–350ng/dL Testosterone – 190μg/day 60μg/day 500L/day 0.7–2.8nmol/L 20–81ng/dL Estrone Follicularphase 110μg/day 80μg/day 2200L/day 110–400pmol/L 30–110pg/mL Lutealphase 260μg/day 150μg/day 2200L/day 310–660pmol/L 80–180pg/mL Postmenopause 40μg/day Insignificant 1610L/day 22–230pmol/L 6–60pg/mL Estradiol Follicularphase 90μg/day 80μg/day 1200L/day <37–360pmol/L 10–98pg/mL Lutealphase 250μg/day 240μg/day 1200L/day 699–1250pmol/L 190–341pg/mL Postmenopause 6μg/day Insignificant 910L/day <37–140pmol/L 10–38pg/mL Estronesulfate Follicularphase 100μg/day Insignificant 146L/day 700–3600pmol/L 250–1300pg/mL Lutealphase 180μg/day Insignificant 146L/day 1100–7300pmol/L 400–2600pg/mL Progesterone Follicularphase 2mg/day 1.7mg/day 2100L/day 0.3–3nmol/L 0.1–0.9ng/mL Lutealphase 25mg/day 24mg/day 2100L/day 19–45nmol/L 6–14ng/mL Notesandsources Notes:"Theconcentrationofasteroidinthecirculationisdeterminedbytherateatwhichitissecretedfromglands,therateofmetabolismofprecursororprehormonesintothesteroid,andtherateatwhichitisextractedbytissuesandmetabolized.Thesecretionrateofasteroidreferstothetotalsecretionofthecompoundfromaglandperunittime.Secretionrateshavebeenassessedbysamplingthevenouseffluentfromaglandovertimeandsubtractingoutthearterialandperipheralvenoushormoneconcentration.Themetabolicclearancerateofasteroidisdefinedasthevolumeofbloodthathasbeencompletelyclearedofthehormoneperunittime.Theproductionrateofasteroidhormonereferstoentryintothebloodofthecompoundfromallpossiblesources,includingsecretionfromglandsandconversionofprohormonesintothesteroidofinterest.Atsteadystate,theamountofhormoneenteringthebloodfromallsourceswillbeequaltotherateatwhichitisbeingcleared(metabolicclearancerate)multipliedbybloodconcentration(productionrate=metabolicclearancerate×concentration).Ifthereislittlecontributionofprohormonemetabolismtothecirculatingpoolofsteroid,thentheproductionratewillapproximatethesecretionrate."Sources:Seetemplate. Distribution[edit] Estrogensareplasmaproteinboundtoalbuminand/orsexhormone-bindingglobulininthecirculation. Metabolism[edit] Seealso:Estradiol§ Metabolism,andEstradiol(medication)§ Metabolism EstrogensaremetabolizedviahydroxylationbycytochromeP450enzymessuchasCYP1A1andCYP3A4andviaconjugationbyestrogensulfotransferases(sulfation)andUDP-glucuronyltransferases(glucuronidation).Inaddition,estradiolisdehydrogenatedby17β-hydroxysteroiddehydrogenaseintothemuchlesspotentestrogenestrone.Thesereactionsoccurprimarilyintheliver,butalsoinothertissues. vteEstrogenmetabolisminhumans Estradiol Estronesulfate Estroneglucuronide 2-Hydroxyestrone Estrone 4-Hydroxyestrone 2-Methoxyestrone 16α-Hydroxyestrone 4-Methoxyestrone 17-Epiestriol Estriol 16-Epiestriol 17β-HSD EST STS UGT1A3UGT1A9 CYP450 CYP450 COMT CYP450 COMT unidentified 17β-HSD unidentified Description:Themetabolicpathwaysinvolvedinthemetabolismofestradiolandothernaturalestrogens(e.g.,estrone,estriol)inhumans.Inadditiontothemetabolictransformationsshowninthediagram,conjugation(e.g.,sulfationandglucuronidation)occursinthecaseofestradiolandmetabolitesofestradiolthathaveoneormoreavailablehydroxyl(–OH)groups.Sources:Seetemplatepage. Excretion[edit] Estrogensareexcretedprimarilybythekidneysasconjugatesviatheurine. Medicaluse[edit] Mainarticle:Estrogen(medication) Estrogensareusedasmedications,mainlyinhormonalcontraception,hormonereplacementtherapy,[87]andtotreatgenderdysphoriaintransgenderwomenandothertransfeminineindividualsaspartoffeminizinghormonetherapy.[88] Chemistry[edit] Seealso:Listofestrogens Theestrogensteroidhormonesareestranesteroids. History[edit] Seealso:Estradiol§ History,Estrone§ History,andEstrogen(medication)§ History In1929,AdolfButenandtandEdwardAdelbertDoisyindependentlyisolatedandpurifiedestrone,thefirstestrogentobediscovered.[89]Then,estriolandestradiolwerediscoveredin1930and1933,respectively.Shortlyfollowingtheirdiscovery,estrogens,bothnaturalandsynthetic,wereintroducedformedicaluse.Examplesincludeestriolglucuronide(Emmenin,Progynon),estradiolbenzoate,conjugatedestrogens(Premarin),diethylstilbestrol,andethinylestradiol. ThewordestrogenderivesfromAncientGreek.Itisderivedfrom"oestros"[90](aperiodicstateofsexualactivityinfemalemammals),andgenos(generating).[90]Itwasfirstpublishedintheearly1920sandreferencedas"oestrin".[91]Withtheyears,AmericanEnglishadaptedthespellingofestrogentofitwithitsphoneticpronunciation.Nevertheless,bothestrogenandoestrogenareusednowadays,yetsomestillwishtomaintainitsoriginalspellingasitreflectstheoriginoftheword. Societyandculture[edit] Etymology[edit] ThenameestrogenisderivedfromtheGreekοἶστρος(oistros),literallymeaning"verveorinspiration"butfigurativelysexualpassionordesire,[92]andthesuffix-gen,meaning"producerof". Environment[edit] Arangeofsyntheticandnaturalsubstancesthatpossessestrogenicactivityhavebeenidentifiedintheenvironmentandarereferredtoxenoestrogens.[93] SyntheticsubstancessuchasbisphenolAaswellasmetalloestrogens(e.g.,cadmium). Plantproductswithestrogenicactivityarecalledphytoestrogens(e.g.,coumestrol,daidzein,genistein,miroestrol). Thoseproducedbyfungiareknownasmycoestrogens(e.g.,zearalenone). Estrogensareamongthewiderangeofendocrine-disruptingcompounds(EDCs)becausetheyhavehighestrogenicpotency.WhenanEDCmakesitswayintotheenvironment,itmaycausemalereproductivedysfunctiontowildlife.[94]Theestrogenexcretedfromfarmanimalsmakesitswayintofreshwatersystems.[95]Duringthegerminationperiodofreproductionthefishareexposedtolowlevelsofestrogenwhichmaycausereproductivedysfunctiontomalefish.[96][97] Cosmetics[edit] Somehairshampoosonthemarketincludeestrogensandplacentalextracts;otherscontainphytoestrogens.In1998,therewerecasereportsoffourprepubescentAfrican-Americangirlsdevelopingbreastsafterexposuretotheseshampoos.[98]In1993,theFDAdeterminedthatnotallover-the-countertopicallyappliedhormone-containingdrugproductsforhumanusearegenerallyrecognizedassafeandeffectiveandaremisbranded.Anaccompanyingproposedruledealswithcosmetics,concludingthatanyuseofnaturalestrogensinacosmeticproductmakestheproductanunapprovednewdrugandthatanycosmeticusingtheterm"hormone"inthetextofitslabelingorinitsingredientstatementmakesanimplieddrugclaim,subjectingsuchaproducttoregulatoryaction.[99] Inadditiontobeingconsideredmisbrandeddrugs,productsclaimingtocontainplacentalextractmayalsobedeemedtobemisbrandedcosmeticsiftheextracthasbeenpreparedfromplacentasfromwhichthehormonesandotherbiologicallyactivesubstanceshavebeenremovedandtheextractedsubstanceconsistsprincipallyofprotein.TheFDArecommendsthatthissubstancebeidentifiedbyanameotherthan"placentalextract"anddescribingitscompositionmoreaccuratelybecauseconsumersassociatethename"placentalextract"withatherapeuticuseofsomebiologicalactivity.[99] Seealso[edit] Listofsteroidabbreviations Breastfeedingandfertility References[edit] ^abcHuether,SueE.;McCance,KathrynL.(2019).UnderstandingPathophysiology.ElsevierHealthSciences.p. 767.ISBN 978-0-32-367281-8.Estrogenisagenerictermforanyofthreesimilarhormonesderivedfromcholesterol:estradiol,estrone,andestriol. ^Satoskar,R.S.;Rege,Nirmala;Bhandarkar,S.D.(2017).PharmacologyandPharmacotherapeutics.ElsevierHealthSciences.p. 943.ISBN 978-8-13-124941-3.Thenaturalestrogensaresteroids.However,typicalestrogenicactivityisalsoshownbychemicalswhicharenotsteroids.Hence,theterm'estrogen'isusedasagenerictermtodescribeallthecompoundshavingestrogenicactivity. ^Delgado,BenjaminJ.;Lopez-Ojeda,Wilfredo(20December2021)."Estrogen".StatPearls[Internet].StatPearlsPublishing.PMID 30855848.Estrogenisasteroidhormoneassociatedwiththefemalereproductiveorgansandisresponsibleforthedevelopmentoffemalesexualcharacteristics.Estrogenisoftenreferredtoasestrone,estradiol,andestriol....Syntheticestrogenisalsoavailableforclinicaluse,designedtoincreaseabsorptionandeffectivenessbyalteringtheestrogenchemicalstructurefortopicalororaladministration.Syntheticsteroidestrogensincludeethinylestradiol,estradiolvalerate,estropipate,conjugateesterifiedestrogen,andquinestrol. 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Externallinks[edit] NusseyandWhitehead:Endocrinology,anintegratedapproach,TaylorandFrancis2001.Freeonlinetextbook. vteEstradiolTopics Estradiol(asahormone) Estradiol(asamedication) Pharmacodynamicsofestradiol Pharmacokineticsofestradiol Estrogen(asahormone) Estrogen(asamedication) Menopausalhormonetherapy Feminizinghormonetherapy Estradiol-containingbirthcontrolpill Combinedinjectablebirthcontrol High-doseestrogen Hydroxylationofestradiol Esters Estradiolacetate Estradiolacetylsalicylate Estradiolanthranilate Estradiolbenzoatebutyrate Estradiolbenzoatecyclooctenylether Estradiolbenzoate Estradiolbutyrylacetate Estradiolcyclooctylacetate Estradiolcypionate Estradioldecanoate Estradioldiacetate Estradioldibutyrate Estradioldienantate Estradioldipropionate Estradioldistearate Estradioldisulfate Estradioldiundecylate Estradioldiundecylenate Estradiolenantate Estradiolfuroate Estradiolglucuronide Estradiolhemisuccinate Estradiolhexahydrobenzoate Estradiolmonopropionate Estradiolmustard Estradiolpalmitate Estradiolphenylpropionate Estradiolphosphate Estradiolpivalate Estradiolpropoxyphenylpropionate Estradiolsalicylate Estradiolstearate Estradiolsulfamate Estradiolsulfate Estradiolundecylate Estradiolundecylenate Estradiolvalerate Estramustinephosphate(estradiolnormustinephosphate) Estrogenester Polyestradiolphosphate Related Estrone Estriol Estetrol Ethinylestradiol Conjugatedestrogens Esterifiedestrogens Estronesulfate Estropipate(piperazineestronesulfate) vteHormonesEndocrineglandsHypothalamic-pituitaryHypothalamus GnRH TRH Dopamine CRH GHRH Somatostatin(GHIH) MCH Posteriorpituitary Oxytocin Vasopressin Anteriorpituitary FSH LH TSH Prolactin POMC CLIP ACTH MSH Endorphins Lipotropin GH Adrenalaxis Adrenalcortex Aldosterone Cortisol Cortisone DHEA DHEA-S Androstenedione Adrenalmedulla Adrenaline Norepinephrine Thyroid Thyroidhormones T3 T4 Calcitonin Thyroidaxis Parathyroid PTH GonadalaxisTestis Testosterone AMH Inhibin Ovary Estradiol Progesterone Activin Inhibin Relaxin GnSAF Placenta hCG HPL Estrogen Progesterone Pancreas Glucagon Insulin Amylin Somatostatin Pancreaticpolypeptide Pinealgland Melatonin N,N-Dimethyltryptamine 5-Methoxy-N,N-dimethyltryptamine OtherThymus Thymosins Thymosinα1 Betathymosins Thymopoietin Thymulin DigestivesystemStomach Gastrin Ghrelin Duodenum CCK Incretins GIP GLP-1 Secretin Motilin VIP Ileum Enteroglucagon PeptideYY Liver/other Insulin-likegrowthfactor IGF-1 IGF-2 Adiposetissue Leptin Adiponectin Resistin Skeleton Osteocalcin Kidney Renin EPO Calcitriol Prostaglandin Heart Natriureticpeptide ANP BNP vteEndogenoussteroidsPrecursors Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone 11β-Hydroxypregnenolone 17α-Hydroxypregnenolone 21-Hydroxypregnenolone 17α,21-Dihydroxypregnenolone 11β,17α,21-Trihydroxypregnenolone CorticosteroidsGlucocorticoids 3α,5α-Tetrahydrocorticosterone 5α-Dihydrocorticosterone 11-Deoxycorticosterone 11-Deoxycortisol 11-Ketoprogesterone 21-Deoxycortisol 21-Deoxycortisone Corticosterone Cortisol Cortisone 17α-Hydroxypregnenolone 17α-Hydroxyprogesterone Pregnenolone Progesterone Metabolites:5α-Dihydrocortisol 3α,5α-Tetrahydrocortisol Mineralocorticoids 5α-Dihydroaldosterone 11-Dehydrocorticosterone(11-oxocorticosterone,17-deoxycortisone) 11-Deoxycortisol 11-Deoxycorticosterone 11β-Hydroxyprogesterone(21-deoxycorticosterone) 18-Hydroxy-11-deoxycorticosterone 18-Hydroxycorticosterone 18-Hydroxyprogesterone Aldosterone Corticosterone Cortisol SexsteroidsAndrogens 11-Ketodihydrotestosterone 11-Ketotestosterone 7β-Hydroxyepiandrosterone 11β-Hydroxyandrostenedione Adrenosterone(11-ketoandrostenedione) Androstenediol Androstenedione Androsterone Dehydroandrosterone DHEA DHEAsulfate Dihydrotestosterone Epiandrosterone Epitestosterone 16α-Hydroxyandrostenedione 16α-Hydroxy-DHEA 16α-Hydroxy-DHEAsulfate Testosterone Metabolites:3α-Androstanediol 3α-Androstanediolglucuronide 3β-Androstanediol 5β-Dihydrotestosterone 3α-Etiocholanediol 3β-Etiocholanediol Androstanetriols Androstenediolsulfate Androsteroneglucuronide Androsteronesulfate Dihydrotestosteroneglucuronide Dihydrotestosteronesulfate Etiocholanedione Etiocholanolone Etiocholanoloneglucuronide Epietiocholanolone Testosteroneglucuronide Testosteronesulfate Estrogens Estranes:Estetrol Estradiol Estrone Estriol 17α-Estradiol 16β-Epiestriol(16β-hydroxyestradiol) 17α-Epiestriol(16α-hydroxy-17α-estradiol) 16β,17α-Epiestriol(16β-hydroxy-17α-estradiol) 2-Hydroxyestradiol 2-Hydroxyestriol 2-Hydroxyestrone 4-Hydroxyestradiol 4-Hydroxyestriol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 16α-Hydroxyestrone 16β-Hydroxyestrone 16-Ketoestradiol 16-Ketoestrone Others:27-Hydroxycholesterol 3α-Androstanediol 3β-Androstanediol 4-Androstenedione 5-Androstenediol DHEA DHEAsulfate 7-Keto-DHEA 7α-Hydroxy-DHEA 16α-Hydroxy-DHEA Metabolites:2-Methoxyestradiol 2-Methoxyestrone 2-Methoxyestriol 4-Methoxyestriol Estradioldisulfate Estradiolglucuronide Estradiol3-glucuronide Estradiol3-glucuronide17β-sulfate Estradiolsulfate Estradiol17β-sulfate Estroneglucuronide Estronesulfate Estriolglucuronide Estriolsulfate Lipoidalestradiol(e.g.,estradiolstearate,estradiolpalmitate) Progestogens Progesterone 16α-Hydroxyprogesterone 17α-Hydroxyprogesterone 20α-Dihydroprogesterone 20β-Dihydroprogesterone 5α-Dihydroprogesterone 11-Deoxycorticosterone 5α-DHDOC Metabolites:Allopregnanediol Pregnanediol Pregnanediolglucuronide Pregnanetriol Neurosteroids Cholestanes:24S-Hydroxycholesterol Cholesterol Pregnanes:3α-Dihydroprogesterone 3β-Dihydroprogesterone 5α-Dihydrocorticosterone 5α-Dihydroprogesterone 5β-Dihydroprogesterone Allopregnanolone Corticosterone DHC DHDOC 11-Deoxycorticosterone Epipregnanolone Isopregnanolone Pregnanolone Pregnenolone Pregnenolonesulfate Progesterone THB THDOC Androstanes:3α-Androstanediol 3α-Androstenol 7-Keto-DHEA 7α-Hydroxy-DHEA 7β-Hydroxy-DHEA 7α-Hydroxyepiandrosterone 7β-Hydroxyepiandrosterone Androsterone DHEA DHEAsulfate Etiocholanolone Pheromones:3α-Androstenol 3β-Androstenol Androstadienol Androstadienone Androstenone Androsterone Estratetraenol Others VitaminD:7-Dehydrocholesterol Calcidiol/Calcifediol Calcitriol Cholecalciferol Others:7α-Hydroxycholesterol 11α-Hydroxyprogesterone 11β-Hydroxyprogesterone Cholesterolsulfate vteEstrogensandantiestrogensEstrogensERagonists Steroidal:Alfatradiol Certainandrogens/anabolicsteroids(e.g.,testosterone,testosteroneesters,methyltestosterone,metandienone,nandroloneesters)(viaestrogenicmetabolites) Certainprogestins(e.g.,norethisterone,noretynodrel,etynodioldiacetate,tibolone) Clomestrone Cloxestradiolacetate Conjugatedestriol Conjugatedestrogens Epiestriol Epimestrol Esterifiedestrogens Estetrol† Estradiol Estradiolesters(e.g.,estradiolacetate,estradiolbenzoate,estradiolcypionate,estradiolenanthate,estradiolundecylate,estradiolvalerate,polyestradiolphosphate,estradiolestermixtures(Climacteron)) Estramustinephosphate Estriol Estriolesters(e.g.,estriolsuccinate,polyestriolphosphate) Estrogenicsubstances Estrone Estroneesters Estronesulfate Estropipate(piperazineestronesulfate) Ethinylestradiol# Ethinylestradiolsulfonate Hydroxyestronediacetate Mestranol Methylestradiol Moxestrol Nilestriol Prasterone(dehydroepiandrosterone;DHEA) Prasteroneenanthate Prasteronesulfate Promestriene Quinestradol Quinestrol Nonsteroidal:Benzestrol Bifluranol Chlorotrianisene Dienestrol Dienestroldiacetate Diethylstilbestrol(stilbestrol) Diethylstilbestrolesters/ethers Dimestrol(diethylstilbestroldimethylether) Fosfestrol(diethylstilbestroldiphosphate) Mestilbol(diethylstilbestrolmonomethylether) Doisynoestrol(fenocycline) Hexestrol Hexestrolesters Methallenestril Methestrol(promethestrol) Methestroldipropionate(promethestroldipropionate) Paroxypropione Quadrosilan Triphenylbromoethylene Triphenylchloroethylene Zeranol Progonadotropins Antiandrogens(e.g.,bicalutamide) GnRHagonists(e.g.,GnRH(gonadorelin),leuprorelin) Gonadotropins(e.g.,FSH,LH) AntiestrogensERantagonists(incl.SERMs/SERDs) Acolbifene† Anordrin Bazedoxifene Broparestrol Clomifene# Cyclofenil Enclomifene† Epitiostanol Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Raloxifene Tamoxifen# Toremifene Exclusivelyantagonistic:Fulvestrant Noncompetitiveinhibitors:Trilostane Aromataseinhibitors First-generation:Aminoglutethimide Testolactone Second-generation:Fadrozole Formestane Third-generation:Anastrozole Exemestane Letrozole Antigonadotropins Androgens/anabolicsteroids(e.g.,testosterone,testosteroneesters,nandroloneesters,oxandrolone,fluoxymesterone) D2receptorantagonists(prolactinreleasers)(e.g.,domperidone,metoclopramide,risperidone,haloperidol,chlorpromazine,sulpiride) GnRHagonists(e.g.,leuprorelin,goserelin) GnRHantagonists(e.g.,cetrorelix,elagolix) Progestogens(e.g.,chlormadinoneacetate,cyproteroneacetate,gestonoronecaproate,hydroxyprogesteronecaproate,medroxyprogesteroneacetate,megestrolacetate) Others Mixedmechanismofaction:Danazol Gestrinone Androstenedioneimmunogens:Androvax(androstenedionealbumin) Ovandrotonealbumin(Fecundin) #WHO-EM ‡Withdrawnfrommarket Clinicaltrials: †PhaseIII §NevertophaseIII Seealso Estrogenreceptormodulators Androgensandantiandrogens Progestogensandantiprogestogens Listofestrogens vteEstrogenreceptormodulatorsERAgonists Steroidal:2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one(DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol(16β-hydroxy-17α-estradiol) 17α-Estradiol(alfatradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol(16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abirateroneacetate Alestramustine Almestrone Anabolicsteroids(e.g.,testosteroneandesters,methyltestosterone,metandienone(methandrostenolone),nandroloneandesters,manyothers;viaestrogenicmetabolites) Atrimustine Bolandiol Bolandioldipropionate Butolame Clomestrone Cloxestradiol Cloxestradiolacetate Conjugatedestriol Conjugatedestrogens Cyclodiol Cyclotriol DHEA DHEA-S ent-Estradiol Epiestriol(16β-epiestriol,16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63(ORG-37663) Esterifiedestrogens Estetrol Estradiol Estradiolesters Lipoidalestradiol Polyestradiolphosphate Estramustine Estramustinephosphate Estrapronicate Estrazinol Estriol Estriolesters Polyestriolphosphate Estrofurate Estrogenicsubstances Estromustine Estrone Estroneesters Estronemethylether Estropipate Etamestrol(eptamestrol) Ethinylandrostenediol Ethandrostate Ethinylestradiol Ethinylestradiol3-benzoate Ethinylestradiolsulfonate Ethinylestriol Ethylestradiol Etynodiol Etynodioldiacetate Hexolame Hippulin Hydroxyestronediacetate Lynestrenol Lynestrenolphenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Nonsteroidal:(R,R)-THC (S,S)-THC 2,8-DHHHC β-LGND1 β-LGND2(GTx-878) AC-186 Allenestrol Allenolicacid Benzestrol Bifluranol Bisdehydrodoisynolicacid Butestrol Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol Dienestroldiacetate Diethylstilbestrol Diethylstilbestrolesters Dimestrol(dianisylhexene) Dimethylstilbestrol Doisynoestrol(fenocycline) Doisynolicacid Efavirenz ERB-196(WAY-202196) Erteberel(SERBA-1,LY-500307) Estrobin(DBE) Fenestrel FERb033 Fosfestrol(diethylstilbestroldiphosphate) Furostilbestrol(diethylstilbestroldifuroate) GTx-758 Hexestrol Hexestrolesters ICI-85966(Stilbostat) M2613 meso-Butestrol meso-Hexestrol Mestilbol Methallenestril Methestrol Methestroldipropionate Paroxypropione Pentafluranol Phenestrol Prinaberel(ERB-041,WAY-202041) Propylpyrazoletriol Quadrosilan SC-3296 SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene(triphenylpropene) WAY-166818 WAY-169916 WAY-200070 WAY-204688(SIM-688) WAY-214156 Unknown/unsorted:ERB-26 ERA-45 ERB-79 ZK-283197 Xenoestrogens:Anise-related(e.g.,anethole,anol,dianethole,dianol,photoanethole) Chalconoids(e.g.,isoliquiritigenin,phloretin,phlorizin(phloridzin),wedelolactone) Coumestans(e.g.,coumestrol,psoralidin) Flavonoids(incl.7,8-DHF,8-prenylnaringenin,apigenin,baicalein,baicalin,biochaninA,calycosin,catechin,daidzein,daidzin,ECG,EGCG,epicatechin,equol,formononetin,glabrene,glabridin,genistein,genistin,glycitein,kaempferol,liquiritigenin,mirificin,myricetin,naringenin,penduletin,pinocembrin,prunetin,puerarin,quercetin,tectoridin,tectorigenin) Lavenderoil Lignans(e.g.,enterodiol,enterolactone,nyasol(cis-hinokiresinol)) Metalloestrogens(e.g.,cadmium) Pesticides(e.g.,alternariol,dieldrin,endosulfan,fenarimol,HPTE,methiocarb,methoxychlor,triclocarban,triclosan) Phytosteroids(e.g.,digitoxin(digitalis),diosgenin,guggulsterone) Phytosterols(e.g.,β-sitosterol,campesterol,stigmasterol) Resorcylicacidlactones(e.g.,zearalanone,α-zearalenol,β-zearalenol,zearalenone,zeranol(α-zearalanol),taleranol(teranol,β-zearalanol)) Steroid-like(e.g.,deoxymiroestrol,miroestrol) Stilbenoids(e.g.,resveratrol,rhaponticin) Syntheticxenoestrogens(e.g.,alkylphenols,bisphenols(e.g.,BPA,BPF,BPS),DDT,parabens,PBBs,PHBA,phthalates,PCBs) Others(e.g.,agnuside,rotundifuran) Mixed(SERMs) 2-Phenylbenzofuran 2-Phenylbenzothiophene 4'-Hydroxynorendoxifen 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordiol Anordrin Arzoxifene Bazedoxifene Brilanestrant Broparestrol Camizestrant Chlorotrianisene Clomifene Clomifenoxide CN-55945-27 Cyclofenil D-15413 Desmethylchlorotrianisene Droloxifene Elacestrant Enclomifene Endoxifen Etacstil(GW-5638,DPC-974) Ethamoxytriphetol(MER-25) Femarelle Fispemifene GW-7604 ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LN-1643 LN-2299 LY-117018 Menerba Miproxifene Miproxifenephosphate MRL-37 Nafoxidine Nitromifene NNC45-0095 NNC45-0320 NNC45-0781 NNC45-1506 Ormeloxifene Ospemifene Panomifene Pipendoxifene Promensil Raloxifene Rimostil(P-081) Spironolactone SS1010 Tamoxifen TAS-108(SR-16234) Toremifene Trioxifene TZE-5323 U-11555A U-11634 Y-134 Zindoxifene Zuclomifene Antagonists (R,R)-THC 7β-Hydroxy-DHEA Chloroindazole Cytestrolacetate EM-800(SCH-57050) Epitiostanol ERA-90 ERB-88 Fulvestrant(ICI-182780) Glyceollins(I,II,III,IV) ICI-164384 MDL-101906 Mepitiostane Methylepitiostanol Methylpiperidinopyrazole MIBE Oxabicycloheptenesulfonate Phenytoin PHTPP Prochloraz RU-39411 RU-58668 SS1020 TAS-108(SR-16234) ZB716 ZK-164015 ZK-191703 Coregulator-bindingmodulators:ERX-11 Noncompetitiveinhibitors:Trilostane GPERAgonists 2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene(4-hydroxytamoxifen) Aldosterone Atrazine BisphenolA Daidzein DDT(p,p'-DDT,o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant(ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Niacinamide Nonylphenol Oleuropein PCBs(2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin Antagonists CCL18 Estriol G-15 G-36 MIBE Unknown Diethylstilbestrol Zearalenone Seealso Receptor/signalingmodulators Estrogensandantiestrogens Androgenreceptormodulators Progesteronereceptormodulators Listofestrogens Authoritycontrol:Nationallibraries France(data) Germany Israel UnitedStates Retrievedfrom"https://en.wikipedia.org/w/index.php?title=Estrogen&oldid=1087065153" 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