Dehydroepiandrosterone - Wikipedia

Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. ... It is one of the most abundant circulating steroids ... Dehydroepiandrosterone FromWikipedia,thefreeencyclopedia Jumptonavigation Jumptosearch ThisarticleisaboutDHEAasahormone.Foritsuseasamedicationorsupplement,seePrasterone.Forotheruses,seeDHEA(disambiguation). FortheprecursorhormoneofDHEAproducedmainlyintheadrenalcortex,DHEAsulfateorDHEA-S,seeDehydroepiandrosteronesulfate. Dehydroepiandrosterone Names IUPACname 3β-Hydroxyandrost-5-en-17-one PreferredIUPACname (3aS,3bR,7S,9aR,9bS,11aS)-7-Hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-one Othernames Androstenolone;Prasterone;Androst-5-en-3β-ol-17-one;5,6-Didehydroepiandrosterone;[1]Dehydroisoepiandrosterone Identifiers CASNumber 53-43-0 Y 3Dmodel(JSmol) Interactiveimage ChEBI CHEBI:28689 Y ChEMBL ChEMBL90593 Y ChemSpider 5670 Y DrugBank DB01708 Y ECHAInfoCard 100.000.160 PubChemCID 5881 UNII 459AG36T1B Y CompToxDashboard(EPA) DTXSID4020379 InChI InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1 YKey: FMGSKLZLMKYGDP-USOAJAOKSA-N Y SMILES O=C3[C@]2(CC[C@@H]1[C@@]4(C(=C/C[C@H]1[C@@H]2CC3)\C[C@@H](O)CC4)C)C Properties Chemicalformula C19H28O2 Molarmass 288.424g/mol Meltingpoint 148.5 Pharmacology ATCvetcode QA14AA07(WHO)G03EA03(WHO)(combinationwithestrogen) Routesofadministration Bymouth,vaginal(insert),intramuscularinjection(asprasteroneenanthate),injection(asprasteronesodiumsulfate) Pharmacokinetics: Bioavailability 50%[2] Metabolism Hepatic[2] Biologicalhalf-life DHEA:25 minutes[3]DHEA-S:11 hours[3] Excretion Urine Exceptwhereotherwisenoted,dataaregivenformaterialsintheirstandardstate(at25 °C[77 °F],100 kPa). Y verify (whatis YN ?) Infobox references Chemicalcompound Dehydroepiandrosterone(DHEA),alsoknownasandrostenolone,isanendogenoussteroidhormoneprecursor.[4]Itisoneofthemostabundantcirculatingsteroidsinhumans.[5]DHEAisproducedintheadrenalglands,[6]thegonads,andthebrain.[7]Itfunctionsasametabolicintermediateinthebiosynthesisoftheandrogenandestrogensexsteroidsbothinthegonadsandinvariousothertissues.[4][8][9]However,DHEAalsohasavarietyofpotentialbiologicaleffectsinitsownright,bindingtoanarrayofnuclearandcellsurfacereceptors,[10]andactingasaneurosteroidandmodulatorofneurotrophicfactorreceptors.[11] IntheUnitedStates,DHEAissoldasanover-the-countersupplement,andmedicationcalledprasterone. Contents 1Biologicalfunction 1.1Asanandrogen 1.2Asanestrogen 1.3Asaneurosteroid 2Biologicalactivity 2.1Hormonalactivity 2.1.1Androgenreceptor 2.1.2Estrogenreceptors 2.1.3Othernuclearreceptors 2.2Neurosteroidactivity 2.2.1Neurotransmitterreceptors 2.2.2Neurotrophinreceptors 2.2.3Microtubule-associatedprotein2 2.3Otheractivity 2.3.1G6PDHinhibitor 2.3.2Cancer 2.3.3Miscellaneous 3Biochemistry 3.1Biosynthesis 3.1.1Increasingendogenousproduction 3.2Distribution 3.3Metabolism 3.3.1Pregnancy 3.4Levels 3.5Measurement 4Chemistry 4.1Isomers 5History 6Seealso 7References 8Furtherreading Biologicalfunction[edit] Asanandrogen[edit] DHEAandotheradrenalandrogenssuchasandrostenedione,althoughrelativelyweakandrogens,areresponsiblefortheandrogeniceffectsofadrenarche,suchasearlypubicandaxillaryhairgrowth,adult-typebodyodor,increasedoilinessofhairandskin,andmildacne.[12][13][14]DHEAispotentiatedlocallyviaconversionintotestosteroneanddihydrotestosterone(DHT)intheskinandhairfollicles.[4]Womenwithcompleteandrogeninsensitivitysyndrome(CAIS),whohaveanon-functionalandrogenreceptor(AR)andareimmunetotheandrogeniceffectsofDHEAandotherandrogens,haveabsentoronlysparse/scantypubicandaxillaryhairandbodyhairingeneral,demonstratingtheroleofDHEAandotherandrogensinbodyhairdevelopmentatbothadrenarcheandpubarche.[15][16][17][18] Asanestrogen[edit] DHEAisaweakestrogen.[4][10][19]Inaddition,itistransformedintopotentestrogenssuchasestradiolincertaintissuessuchasthevagina,andtherebyproducesestrogeniceffectsinsuchtissues.[4] Asaneurosteroid[edit] Asaneurosteroidandneurotrophin,DHEAhasimportanteffectsinthecentralnervoussystem.[20][21][22] Biologicalactivity[edit] Hormonalactivity[edit] Androgenreceptor[edit] AlthoughitfunctionsasanendogenousprecursortomorepotentandrogenssuchastestosteroneandDHT,DHEAhasbeenfoundtopossesssomedegreeofandrogenicactivityinitsownright,actingasalowaffinity(Ki=1μM),weakpartialagonistoftheandrogenreceptor(AR).However,itsintrinsicactivityatthereceptorisquiteweak,andonaccountofthat,duetocompetitionforbindingwithfullagonistsliketestosterone,itcanactuallybehavemorelikeanantagonistdependingoncirculatingtestosteroneanddihydrotestosterone(DHT)levels,andhence,likeanantiandrogen.However,itsaffinityforthereceptorisverylow,andforthatreason,isunlikelytobeofmuchsignificanceundernormalcircumstances.[19][23] Estrogenreceptors[edit] Inadditiontoitsaffinityfortheandrogenreceptor,DHEAhasalsobeenfoundtobindto(andactivate)theERαandERβestrogenreceptorswithKivaluesof1.1μMand0.5μM,respectively,andEC50valuesof>1μMand200nM,respectively.ThoughitwasfoundtobeapartialagonistoftheERαwithamaximalefficacyof30–70%,theconcentrationsrequiredforthisdegreeofactivationmakeitunlikelythattheactivityofDHEAatthisreceptorisphysiologicallymeaningful.Remarkablyhowever,DHEAactsasafullagonistoftheERβwithamaximalresponsesimilartooractuallyslightlygreaterthanthatofestradiol,anditslevelsincirculationandlocaltissuesinthehumanbodyarehighenoughtoactivatethereceptortothesamedegreeasthatseenwithcirculatingestradiollevelsatsomewhathigherthantheirmaximal,non-ovulatoryconcentrations;indeed,whencombinedwithestradiolwithbothatlevelsequivalenttothoseoftheirphysiologicalconcentrations,overallactivationoftheERβwasdoubled.[10][19] Othernuclearreceptors[edit] DHEAdoesnotbindtooractivatetheprogesterone,glucocorticoid,ormineralocorticoidreceptors.[19][24]OthernuclearreceptortargetsofDHEAbesidestheandrogenandestrogenreceptorsincludethePPARα,PXR,andCAR.[25]However,whereasDHEAisaligandofthePPARαandPXRinrodents,itisnotinhumans.[26]Inadditiontodirectinteractions,DHEAisthoughttoregulateahandfulofotherproteinsviaindirect,genomicmechanisms,includingtheenzymesCYP2C11and11β-HSD1–thelatterofwhichisessentialforthebiosynthesisoftheglucocorticoidssuchascortisolandhasbeensuggestedtobeinvolvedintheantiglucocorticoideffectsofDHEA–andthecarrierproteinIGFBP1.[19][27] Neurosteroidactivity[edit] Neurotransmitterreceptors[edit] DHEAhasbeenfoundtodirectlyactonseveralneurotransmitterreceptors,includingactingasapositiveallostericmodulatoroftheNMDAreceptor,asanegativeallostericmodulatoroftheGABAAreceptor,andasanagonistoftheσ1receptor.[28][25] Neurotrophinreceptors[edit] In2011,thesurprisingdiscoverywasmadethatDHEA,aswellasitssulfateester,DHEA-S,directlybindtoandactivateTrkAandp75NTR,receptorsofneurotrophinslikenervegrowthfactor(NGF)andbrain-derivedneurotrophicfactor(BDNF),withhighaffinity.[25][29]DHEAwassubsequentlyalsofoundtobindtoTrkBandTrkCwithhighaffinity,thoughitonlyactivatedTrkCnotTrkB.[25][30]DHEAandDHEA-Sboundtothesereceptorswithaffinitiesinthelownanomolarrange(around5 nM),whichwerenonethelessapproximatelytwoordersofmagnitudelowerrelativetohighlypotentpolypeptideneurotrophinslikeNGF(0.01–0.1 nM).[25][29][30]Inanycase,DHEAandDHEA-Sbothcirculateatrequisiteconcentrationstoactivatethesereceptorsandwerethusidentifiedasimportantendogenousneurotrophicfactors.[25][29]Theyhavesincebeenlabeled"steroidalmicroneurotrophins",duetotheirsmall-moleculeandsteroidalnaturerelativetotheirpolypeptideneurotrophincounterparts.[31]SubsequentresearchhassuggestedthatDHEAand/orDHEA-Smayinfactbephylogeneticallyancient"ancestral"ligandsoftheneurotrophinreceptorsfromearlyonintheevolutionofthenervoussystem.[25][30]ThefindingsthatDHEAbindstoandpotentlyactivatesneurotrophinreceptorsmayexplainthepositiveassociationbetweendecreasedcirculatingDHEAlevelswithageandage-relatedneurodegenerativediseases.[25][29] Microtubule-associatedprotein2[edit] Similarlytopregnenolone,itssyntheticderivative3β-methoxypregnenolone(MAP-4343),andprogesterone,DHEAhasbeenfoundtobindtomicrotubule-associatedprotein2(MAP2),specificallytheMAP2Csubtype(Kd=27 μM).[25]However,itisunclearwhetherDHEAincreasesbindingofMAP2totubulinlikepregnenolone.[25] Otheractivity[edit] G6PDHinhibitor[edit] DHEAisanuncompetitiveinhibitorofG6PDH(Ki=17 μM;IC50=18.7 μM),andisabletolowerNADPHlevelsandreduceNADPH-dependentfreeradicalproduction.[32][33]Itisthoughtthatthisactionmaypossiblyberesponsibleformuchoftheantiinflammatory,antihyperplastic,chemopreventative,antihyperlipidemic,antidiabetic,andantiobesic,aswellascertainimmunomodulatingactivitiesofDHEA(withsomeexperimentalevidencetosupportthisnotionavailable).[32][33][34][35]However,ithasalsobeensaidthatinhibitionofG6PDHactivitybyDHEAinvivohasnotbeenobservedandthattheconcentrationsrequiredforDHEAtoinhibitG6PDHinvitroareveryhigh,thusmakingthepossiblecontributionofG6PDHinhibitiontotheeffectsofDHEAuncertain.[33] Cancer[edit] DHEAsupplementshavebeenpromotedaschemopreventative,[32][33][34][35]fortheirclaimedcancerpreventionproperties.Thereisscientificevidencetosupporttheseclaims.[32][33][34][35] Miscellaneous[edit] DHEAhasbeenfoundtocompetitivelyinhibitTRPV1.[28] Biochemistry[edit] Comprehensiveoverviewofsteroidogenesis,showingDHEAatleftamongtheandrogens.[36] Biosynthesis[edit] DHEAisproducedinthezonareticularisoftheadrenalcortexunderthecontrolofadrenocorticotropichormone(ACTH)andbythegonadsunderthecontrolofgonadotropin-releasinghormone(GnRH).[37][38]Itisalsoproducedinthebrain.[39]DHEAissynthesizedfromcholesterolviatheenzymescholesterolside-chaincleavageenzyme(CYP11A1;P450scc)and17α-hydroxylase/17,20-lyase(CYP17A1),withpregnenoloneand17α-hydroxypregnenoloneasintermediates.[40]Itisderivedmostlyfromtheadrenalcortex,withonlyabout10%beingsecretedfromthegonads.[41][42][43]Approximately50to70%ofcirculatingDHEAoriginatesfromdesulfationofDHEA-Sinperipheraltissues.[41]DHEA-Sitselforiginatesalmostexclusivelyfromtheadrenalcortex,with95to100%beingsecretedfromtheadrenalcortexinwomen.[37][43] Increasingendogenousproduction[edit] RegularexerciseisknowntoincreaseDHEAproductioninthebody.[44][45]CalorierestrictionhasalsobeenshowntoincreaseDHEAinprimates.[46]SometheorizethattheincreaseinendogenousDHEAbroughtaboutbycalorierestrictionispartiallyresponsibleforthelongerlifeexpectancyknowntobeassociatedwithcalorierestriction.[47] Distribution[edit] Inthecirculation,DHEAismainlyboundtoalbumin,withasmallamountboundtosexhormone-bindingglobulin(SHBG).[48][49]ThesmallremainderofDHEAnotassociatedwithalbuminorSHBGisunboundandfreeinthecirculation.[48] DHEAeasilycrossestheblood–brainbarrierintothecentralnervoussystem.[39] Metabolism[edit] DHEAistransformedintoDHEA-SbysulfationattheC3βpositionviathesulfotransferaseenzymesSULT2A1andtoalesserextentSULT1E1.[40][50][51]Thisoccursnaturallyintheadrenalcortexandduringfirst-passmetabolismintheliverandintestineswhenexogenousDHEAisadministeredorally.[50]LevelsofDHEA-Sincirculationareapproximately250to300timesthoseofDHEA.[20]DHEA-SinturncanbeconvertedbackintoDHEAinperipheraltissuesviasteroidsulfatase(STS).[52][53] Theterminalhalf-lifeofDHEAisshortatonly15to30 minutes.[54]Incontrast,theterminalhalf-lifeofDHEA-Sisfarlonger,at7to10 hours.[54]AsDHEA-ScanbeconvertedbackintoDHEA,itservesasacirculatingreservoirforDHEA,therebyextendingthedurationofDHEA.[55][20] MetabolitesofDHEAincludeDHEA-S,7α-hydroxy-DHEA,7β-hydroxy-DHEA,7-keto-DHEA,7α-hydroxyepiandrosterone,and7β-hydroxyepiandrosterone,aswellasandrostenediolandandrostenedione.[8] Pregnancy[edit] Duringpregnancy,DHEA-Sismetabolizedintothesulfatesof16α-hydroxy-DHEAand15α-hydroxy-DHEAinthefetalliverasintermediatesintheproductionoftheestrogensestriolandestetrol,respectively. Levels[edit] Priortopuberty,DHEAandDHEA-Slevelselevateupondifferentiationofthezonareticularisoftheadrenalcortex.[25]PeaklevelsofDHEAandDHEA-Sareobservedaroundage20,whichisfollowedbyanage-dependentdeclinethroughoutlifeeventuallybacktoprepubertalconcentrations.[25]PlasmalevelsofDHEAinadultmenare10to25 nM,inpremenopausalwomenare5to30 nM,andinpostmenopausalwomenare2to20 nM.[25]Conversely,DHEA-Slevelsareanorderofmagnitudehigherat1–10 μM.[25]LevelsofDHEAandDHEA-Sdeclinetothelowernanomolarandmicromolarrangesinmenandwomenaged60to80 years.[25] DHEAlevelsareasfollows:[56] Adultmen:180–1250 ng/dL Adultwomen:130–980 ng/dL Pregnantwomen:135–810 ng/dL Prepubertalchildren(<1year):26–585 ng/dL Prepubertalchildren(1–5years):9–68 ng/dL Prepubertalchildren(6–12years):11–186 ng/dL Adolescentboys(TannerII–III):25–300 ng/dL Adolescentgirls(TannerII–III):69–605 ng/dL Adolescentboys(TannerIV–V):100–400 ng/dL Adolescentgirls(TannerIV–V):165–690 ng/dL Measurement[edit] AsalmostallDHEAisderivedfromtheadrenalglands,bloodmeasurementsofDHEA-S/DHEAareusefultodetectexcessadrenalactivityasseeninadrenalcancerorhyperplasia,includingcertainformsofcongenitaladrenalhyperplasia.WomenwithpolycysticovarysyndrometendtohaveelevatedlevelsofDHEA-S.[57] Chemistry[edit] Seealso:Listofandrogens/anabolicsteroidsandListofneurosteroids DHEA,alsoknownasandrost-5-en-3β-ol-17-one,isanaturallyoccurringandrostanesteroidanda17-ketosteroid.[58]Itiscloselyrelatedstructurallytoandrostenediol(androst-5-ene-3β,17β-diol),androstenedione(androst-4-ene-3,17-dione),andtestosterone(androst-4-en-17β-ol-3-one).[58]DHEAisthe5-dehydroanalogueofepiandrosterone(5α-androstan-3β-ol-17-one)andisalsoknownas5-dehydroepiandrosteroneorasδ5-epiandrosterone.[58] Isomers[edit] Theterm"dehydroepiandrosterone"isambiguouschemicallybecauseitdoesnotincludethespecificpositionswithinepiandrosteroneatwhichhydrogenatomsaremissing.DHEAitselfis5,6-didehydroepiandrosteroneor5-dehydroepiandrosterone.Anumberofnaturallyoccurringisomersalsoexistandmayhavesimilaractivities.SomeisomersofDHEAare1-dehydroepiandrosterone(1-androsterone)and4-dehydroepiandrosterone.[59]Theseisomersarealsotechnically"DHEA",sincetheyaredehydroepiandrosteronesinwhichhydrogensareremovedfromtheepiandrosteroneskeleton. Dehydroandrosterone(DHA)isthe3α-epimerofDHEAandisalsoanendogenousandrogen. History[edit] Seealso:Prasterone§ History DHEAwasfirstisolatedfromhumanurinein1934byAdolfButenandtandKurtTscherning.[60] Seealso[edit] Epigeneticclock References[edit] ^DevillersJ(27April2009).EndocrineDisruptionModeling.CRCPress.pp. 339–.ISBN 978-1-4200-7636-3. ^abCuppMJ,TracyTS(10December2002).DietarySupplements:ToxicologyandClinicalPharmacology.SpringerScience&BusinessMedia.pp. 135–.ISBN 978-1-59259-303-3. ^abOddensBJ,VermeulenA(15November1996).AndrogensandtheAgingMale.CRCPress.pp. 5–.ISBN 978-1-85070-763-9. ^abcdeLabrieF,Luu-TheV,BélangerA,LinSX,SimardJ,PelletierG,LabrieC(November2005)."Isdehydroepiandrosteroneahormone?".J.Endocrinol.187(2):169–96.doi:10.1677/joe.1.06264.PMID 16293766. ^WilliamFGanongMD,'ReviewofMedicalPhysiology',22ndEd,McGrawHill,2005,p.362. ^TheMerckIndex,13thEdition,7798 ^SchulmanRA,DeanC(2007).SolveItWithSupplements.NewYorkCity:Rodale,Inc.p. 100.ISBN 978-1-57954-942-8.DHEA(Dehydroepiandrosterone)isacommonhormoneproducedintheadrenalglands,thegonads,andthebrain. 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^CopelandJL,ConsittLA,TremblayMS(April2002)."Hormonalresponsestoenduranceandresistanceexerciseinfemalesaged19-69years".TheJournalsofGerontology.SeriesA,BiologicalSciencesandMedicalSciences.57(4):B158–65.doi:10.1093/gerona/57.4.B158.PMID 11909881. ^MattisonJA,LaneMA,RothGS,IngramDK(2003)."Calorierestrictioninrhesusmonkeys".ExperimentalGerontology.38(1–2):35–46.doi:10.1016/S0531-5565(02)00146-8.PMID 12543259.S2CID 41481691.. ^RobertsE(February1999)."Theimportanceofbeingdehydroepiandrosteronesulfate(inthebloodofprimates):alongerandhealthierlife?".BiochemicalPharmacology.57(4):329–46.doi:10.1016/S0006-2952(98)00246-9.PMID 9933021.. ^abAlesciS,ManoliI,BlackmanMR(29December2004)."Dehydroepiandrosterone(DHEA)".InCoatesPM,BlackmanMR,CraggGM,LevineM,MossJ,WhiteJD(eds.).EncyclopediaofDietarySupplements(Print).CRCPress.pp. 169–.ISBN 978-0-8247-5504-1. ^BeckerKL(2001).PrinciplesandPracticeofEndocrinologyandMetabolism.LippincottWilliams&Wilkins.pp. 712–.ISBN 978-0-7817-1750-2. ^abMuellerJW,GilliganLC,IdkowiakJ,ArltW,FosterPA(October2015)."TheRegulationofSteroidActionbySulfationandDesulfation".EndocrRev.36(5):526–63.doi:10.1210/er.2015-1036.PMC 4591525.PMID 26213785. ^LashLH(2005).DrugMetabolismandTransport:MolecularMethodsandMechanisms.SpringerScience&BusinessMedia.pp. 353–.ISBN 978-1-59259-832-8. ^MorfinR(2September2003).DHEAandtheBrain.CRCPress.pp. 28–.ISBN 978-0-203-30121-0. ^KarasekM(2006).AgingandAge-relatedDiseases:TheBasics.NovaPublishers.pp. 66–.ISBN 978-1-59454-426-2. ^abWhiteBA,PorterfieldSP(2013).EndocrineandReproductivePhysiology,MosbyPhysiologyMonographSeries(withStudentConsultOnlineAccess),4:EndocrineandReproductivePhysiology.ElsevierHealthSciences.pp. 164–.ISBN 978-0-323-08704-9. ^KalimiMY,RegelsonW(2000).Dehydroepiandrosterone(DHEA):Biochemical,PhysiologicalandClinicalAspects.WalterdeGruyter.pp. 41–.ISBN 978-3-11-016111-3. ^https://www.questdiagnostics.com/hcp/intguide/EndoMetab/EndoManual_AtoZ_PDFs/DHEA.pdf ^BanaszewskaB,SpaczyńskiRZ,PeleszM,PawelczykL(2003)."IncidenceofelevatedLH/FSHratioinpolycysticovarysyndromewomenwithnormo-andhyperinsulinemia".RocznikiAkademiiMedycznejWBialymstoku.48:131–4.PMID 14737959. ^abcElksJ(14November2014).TheDictionaryofDrugs:ChemicalData:ChemicalData,StructuresandBibliographies.Springer.pp. 641–.ISBN 978-1-4757-2085-3. ^EdithJosephy;F.Radt(1December2013).Elsevier'sEncyclopaediaofOrganicChemistry:SeriesIII:CarboisocyclicCondensedCompounds.Springer.pp. 2608–.ISBN 978-3-662-25863-7. ^SchwartzAG,PashkoLL(2001)."Potentialtherapeuticuseofdehydroepiandrosteroneandstructuralanalogs".DiabetesTechnology&Therapeutics.3(2):221–4.doi:10.1089/152091501300209589.PMID 11478328. Furtherreading[edit] LabrieF,MartelC,BélangerA,PelletierG(April2017)."AndrogensinwomenareessentiallymadefromDHEAineachperipheraltissueaccordingtointracrinology".TheJournalofSteroidBiochemistryandMolecularBiology.168:9–18.doi:10.1016/j.jsbmb.2016.12.007.PMID 28153489.S2CID 2620899. 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 vteAndrogensandantiandrogensAndrogens(incl.AAS)ARagonists Testosteronederivatives:Androstenedioldipropionate Boldenoneundecylenate Clostebol Clostebolacetate Clostebolcaproate Clostebolpropionate Cloxotestosteroneacetate Prasterone(dehydroepiandrosterone,DHEA) Prasteroneenanthate(DHEAenanthate) Prasteronesulfate(DHEAsulfate) Quinbolone Testosterone# Testosteroneesters(e.g.,testosteronecypionate,testosteroneenanthate,testosteronepropionate,testosteroneundecanoate,testosteroneestermixtures(Deposterona,Omnadren,Sustanon,TestovironDepot)) Dihydrotestosteronederivatives:Androstanolone(stanolone,dihydrotestosterone,DHT) Androstanoloneesters Bolazinecapronate Drostanolonepropionate(dromostanolonepropionate) Epitiostanol Mepitiostane Mesterolone Metenoloneacetate(methenoloneacetate) Metenoloneenanthate(methenoloneenanthate) Stenboloneacetate 19-Nortestosteronederivatives:Bolandioldipropionate Nandroloneesters(e.g.,nandrolonedecanoate,nandrolonephenylpropionate) Norclostebol Norclostebolacetate Oxabolonecipionate(oxabolonecypionate) Trenboloneacetate Trenbolonehexahydrobenzylcarbonate(trenbolonecyclohexylmethylcarbonate) 17α-Alkylatedtestosteronederivatives:Bolasterone Calusterone Chlorodehydromethyltestosterone(CDMT) Fluoxymesterone Formebolone Metandienone(methandienone,methandrostenolone) Methandriol(methylandrostenediol) Methandriolbisenanthoylacetate Methandrioldipropionate Methandriolpropionate Methyltestosterone Methyltestosterone3-hexylether Oxymesterone Penmesterol Tiomesterone(thiomesterone) 17α-Alkylateddihydrotestosteronederivatives:Androisoxazole Furazabol Mebolazine(dimethazine) Mestanolone Oxandrolone Oxymetholone Stanozolol 17α-Alkylated19-nortestosteronederivatives:Ethylestrenol Mibolerone Norethandrolone Normethandrone(methylestrenolone,normethisterone) Propetandrol(propethandrol) 17α-Vinyltestosteronederivatives:Norvinisterone(vinylnortestosterone) 17α-Ethynyltestosteronederivatives:Danazol Gestrinone Progestins(e.g.,ethisterone(ethynyltestosterone),levonorgestrel,norgestrel,norethisterone(norethindrone),lynestrenol,norgestrienone) Tibolone Progesteronederivatives:Medroxyprogesteroneacetate Progonadotropins Antiestrogens(e.g.,tamoxifen,clomifene) GnRHagonists(e.g.,GnRH(gonadorelin),leuprorelin) Gonadotropins(e.g.,LH,hCG) AntiandrogensARantagonists Steroidal:Abirateroneacetate Canrenone Chlormadinoneacetate Cyproteroneacetate Delmadinoneacetate Dienogest Drospirenone Medrogestone Megestrolacetate Nomegestrolacetate Osateroneacetate Oxendolone Potassiumcanrenoate Spironolactone Nonsteroidal:Apalutamide Bicalutamide Cimetidine Darolutamide Enzalutamide Flutamide Ketoconazole Nilutamide Seviteronel† Topilutamide(fluridil) Steroidogenesisinhibitors5α-Reductase Alfatradiol Dutasteride Epristeride Finasteride Sawpalmettoextract Others Abirateroneacetate Aminoglutethimide Bifluranol Cyproteroneacetate Flutamide Ketoconazole Nilutamide Seviteronel† Spironolactone Antigonadotropins D2receptorantagonists(prolactinreleasers)(e.g.,domperidone,metoclopramide,risperidone,haloperidol,chlorpromazine,sulpiride) Estrogens(e.g.,bifluranol,diethylstilbestrol,estradiol,estradiolesters,ethinylestradiol,ethinylestradiolsulfonate,paroxypropione) GnRHagonists(e.g.,leuprorelin) GnRHantagonists(e.g.,cetrorelix) Progestogens(incl.,chlormadinoneacetate,cyproteroneacetate,hydroxyprogesteronecaproate,gestonoronecaproate,medroxyprogesteroneacetate,megestrolacetate) Others Androstenedioneimmunogens:Androvax(androstenedionealbumin) Ovandrotonealbumin(Fecundin) #WHO-EM ‡Withdrawnfrommarket Clinicaltrials: †PhaseIII §NevertophaseIII Seealso Androgenreceptormodulators Estrogensandantiestrogens Progestogensandantiprogestogens Listofandrogens/anabolicsteroids Biologicalactivity vteAndrogenreceptormodulatorsARAgonists Testosteronederivatives:4-Androstenediol 4-Dehydroepiandrosterone(4-DHEA) 4-Hydroxytestosterone 4,17α-Dimethyltestosterone 5-Androstenedione 11-Ketotestosterone 11β-Hydroxyandrostenedione Adrenosterone(11-ketoandrostenedione,11-oxoandrostenedione) Androstenediol(5-androstenediol) Androstenediol3β-acetate Androstenediol17β-acetate Androstenedioldiacetate Androstenedioldipropionate Androstenedione(4-androstenedione) Atamestane Boldenone Boldenoneundecylenate Boldione(1,4-androstadienedione) Clostebol Clostebolacetate Clostebolcaproate Clostebolpropionate Cloxotestosterone Cloxotestosteroneacetate Dehydroandrosterone DHEA(androstenolone,prasterone;5-DHEA) DHEAenanthate(prasteroneenanthate) DHEAsulfate Exemestane Formestane Plomestane Quinbolone Silandrone Testosterone#(+dutasteride) Testosteroneesters Polytestosteronephloretinphosphate 5α-Dihydrotestosteronederivatives:1-Androstenediol 1-Androstenedione 1-Androsterone(1-andro,1-DHEA) 1-Testosterone 3α-Androstanediol 5α-Androst-2-en-17-one 7β-Hydroxyepiandrosterone 11-Ketodihydrotestosterone Androsterone Bolazine Bolazinecapronate Dihydroethyltestosterone Dihydrofluoxymesterone Dihydromethylandrostenediol Dihydrotestosterone(DHT)(androstanolone,stanolone) Dihydrotestosteroneesters Drostanolone Drostanolonepropionate Epiandrosterone Epitiostanol Mepitiostane Mesabolone Mesterolone Mesterolonecipionate Methyldiazinol Nisterime Nisterimeacetate Prostanozol Stenbolone Stenboloneacetate Testifenon(testiphenon,testiphenone) 19-Nortestosteronederivatives:7α-Methyl-19-norandrostenedione(MENTdione,trestione) 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosteronedodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione 19-Nordehydroepiandrosterone Bolandiol Bolandioldipropionate Bolandione(19-nor-4-androstenedione) Bolmantalate(nandroloneadamantoate) Dienedione Dienolone Dimethandrolone Dimethandrolonebuciclate Dimethandrolonedodecylcarbonate Dimethandroloneundecanoate LS-1727(nandrolone17β-N-(2-chloroethyl)-N-nitrosocarbamate) Methoxydienone(methoxygonadiene) Nandrolone Nandroloneesters Norclostebol Norclostebolacetate Normethandrone(methylestrenolone,normethisterone) Oxabolone Oxabolonecipionate(oxabolonecypionate) Trenbolone Trenboloneacetate Trenboloneenanthate Trenbolonehexahydrobenzylcarbonate Trenboloneundecanoate Trendione Trestolone(MENT) Trestoloneacetate Trestoloneenanthate 5α-Dihydro-19-nortestosteronederivatives:5α-Dihydronandrolone 5α-Dihydrotrestolone 19-Norandrosterone 17α-Alkylatedtestosteronederivatives:Bolasterone Calusterone Chlorodehydromethylandrostenediol(CDMA) Chlorodehydromethyltestosterone(CDMT) Chloromethylandrostenediol(CMA) Enestebol Ethyltestosterone Fluoxymesterone Formebolone Hydroxystenozole Metandienone(methandrostenolone) Methandriol(methylandrostenediol) Methandriolbisenanthoylacetate Methandrioldiacetate Methandrioldipropionate Methandriolpropionate Methylclostebol(chloromethyltestosterone) Methyltestosterone(+esterifiedestrogens) Methyltestosterone3-hexylether Oxymesterone Penmesterol Tiomesterone 17α-Alkylated5α-dihydrotestosteronederivatives:Androisoxazole Desoxymethyltestosterone Furazabol Mebolazine(dimethazine) Mestanolone Metenolone Metenoloneacetate Metenoloneenanthate Methasterone Methyl-1-testosterone Methylepitiostanol Methylstenbolone Oxandrolone Oxymetholone Stanozolol 17α-Alkylated19-nortestosteronederivatives:Bolenol Dimethyldienolone Dimethyltrienolone Ethyldienolone Ethylestrenol Methyldienolone Methylhydroxynandrolone(MOHN,MHN) Metribolone Mibolerone Norboletone Norethandrolone Propetandrol RU-2309 Tetrahydrogestrinone 17α-Alkylated5α-dihydro-19-nortestosteronederivatives:5α-Dihydronorethandrolone 5α-Dihydronormethandrone 17α-Vinyltestosteronederivatives:Norvinisterone(vinylnortestosterone) 17α-Vinyl-19-nortestosteronederivatives:Vinyltestosterone 17α-Ethynyltestosteronederivatives:Danazol Ethinylandrostenediol Ethandrostate Ethisterone(ethynyltestosterone) 5α-Dihydro-17α-ethynyltestosteronederivatives:17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol Dihydroethisterone 17α-Ethynyl-19-nortestosteronederivatives:Δ4-Tibolone Desogestrel Etonogestrel Etynodiol Etynodioldiacetate Gestodene Gestrinone Levonorgestrel Levonorgestrelesters(e.g.,levonorgestrelbutanoate) Lynestrenol Lynestrenolphenylpropionate Norethisterone Norethisteroneesters(e.g.,norethisteroneacetate,norethisteroneenanthate) Norgestrel Norgestrienone Quingestanol Quingestanolacetate Tibolone 5α-Dihydro-17α-ethynyl-19-nortestosteronederivatives:5α-Dihydrolevonorgestrel 5α-Dihydronorethisterone Progesteronederivatives:6α-Methylprogesterone Medroxyprogesteroneacetate Megestrolacetate Others/unsorted:3-Keto-5α-abiraterone 5α-Androstane Alternariol Cl-4AS-1 Drupanol Trilostane ZM-182345 Mixed(SARMs) Nonsteroidal:198RL26 ACP-105 AC-262536 Acetothiolutamide Andarine(acetamidoxolutamide,androxolutamide,GTx-007,S-4) BMS-564929 DTIB Enobosarm(ostarine,MK-2866,GTx-024,S-22) FTBU-1 GSK2881078 GSK-4336A GSK-8698 LG-121071(LGD-121071) LGD-2226 LGD-2941(LGD-122941) LGD-3303 LGD-4033 LY-2452473 JNJ-26146900 JNJ-28330835 JNJ-37654032 ORM-11984 R-1 RAD140 RU-59063 S-1 S-23 S-40503 S-101479 Triclosan Steroidal:EM-9017 MK-0773 TFM-4AS-1 YK-11 Antagonists Steroidal:7α-Thioprogesterone 7α-Thiospironolactone 7α-Thiomethylspironolactone 11α-Hydroxyprogesterone 15β-Hydroxycyproteroneacetate Abiraterone Abirateroneacetate Allyltestosterone Benorterone BOMT Canrenoicacid Canrenone Chlormadinoneacetate Clascoterone Clometerone Cyproheptadine Cyproterone Cyproteroneacetate Delanterone Delmadinoneacetate Dicirenone Dienogest Drospirenone DU-41165 Edogestrone EM-4350 EM-5854 EM-5855 EM-6537 Epitestosterone Galeterone Guggulsterone Ludaterone Medrogestone Megestrolacetate Mespirenone Metogest Mexrenone Mifepristone Nomegestrolacetate Nordinone Osaterone Osateroneacetate Oxendolone Potassiumcanrenoate Promegestone Prorenone Rosterolone RU-15328 SC-5233(spirolactone) Spironolactone Spirorenone Spiroxasone Topterone Trimegestone Trimethyltrienolone(R-2956) Zanoterone Nonsteroidal:5N-Bicalutamide AA560 Antarlides Arabilin Apalutamide Atraricacid AZD-3514 Bakuchiol Bavdegalutamide BAY-1024767 Bicalutamide Bisphenols(e.g.,BADGE,BFDGE,bisphenolA,bisphenolF,bisphenolS) BMS-501949 BMS-570511 BMS-641988 CH5137291 Cimetidine Cioteronel Cyanonilutamide Darolutamide DDT(viametabolitep,p’-DDE) Dieldrin DIMP Endosulfan Enzalutamide EPI-001 EPI-7386 Fenarimol Flutamide Hydroxyflutamide Inocoterone Inocoteroneacetate Ketoconazole Ketodarolutamide Lavenderoil LG-105 LG-120907 LGD-1331 Linuron Methiocarb N-Butylbenzenesulfonamide N-Desmethylapalutamide N-Desmethylenzalutamide Nilutamide ONC1-13B Pentomone PF-998425 Phenothrin Prochloraz Procymidone Proxalutamide Ralaniten(EPI-002) Ralanitenacetate(EPI-506) RD-162 Rezvilutamide Ro2-7239 Ro5-2537 RU-22930 RU-56187 RU-57073 RU-58642 RU-58841 Seviteronel Thalidomide Topilutamide(fluridil) Valproicacid Vinclozolin YM-580 YM-92088 YM-175735 GPRC6AAgonists Cations(incl.aluminum,calcium,gadolinium,magnesium,strontium,zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Aminoacids(incl.L-arginine,L-lysine,L-ornithine) Osteocalcin SHBG Testosterone Seealso Receptor/signalingmodulators Androgensandantiandrogens Estrogenreceptormodulators Progesteronereceptormodulators Listofandrogens/anabolicsteroids 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 vteGABAreceptormodulatorsIonotropicGABAA Agonists:(+)-Catechin Bamaluzole Barbiturates(e.g.,phenobarbital) Beta-Alanine BL-1020 DAVA Dihydromuscimol GABA Gabamide GABOB Gaboxadol(THIP) Homotaurine(tramiprosate,3-APS) Ibotenicacid iso-THAZ iso-THIP Isoguvacine Isomuscimol Isonipecoticacid Kojicamine L-838,417 Lignans(e.g.,honokiol) Methylglyoxal Monastrol Muscimol Nefiracetam Neuroactivesteroids(e.g.,allopregnanolone) Org20599 PF-6372865 Phenibut Picamilon P4S Progabide Propofol Quisqualamine SL-75102 Taurine TACA TAMP Terpenoids(e.g.,borneol) Thiomuscimol Tolgabide ZAPA Positivemodulators(abridged;seehereforafulllist):α-EMTBL Alcohols(e.g.,drinkingalcohol,2M2B) Anabolicsteroids Avermectins(e.g.,ivermectin) Barbiturates(e.g.,phenobarbital) Benzodiazepines(e.g.,diazepam) Bromidecompounds(e.g.,potassiumbromide) Carbamates(e.g.,meprobamate) Carbamazepine Chloralose Chlormezanone Clomethiazole Dihydroergolines(e.g.,ergoloid(dihydroergotoxine)) Etazepine Etifoxine Fenamates(e.g.,mefenamicacid) Flavonoids(e.g.,apigenin,hispidulin) Fluoxetine Flupirtine Imidazoles(e.g.,etomidate) Kavaconstituents(e.g.,kavain) Lanthanum Loreclezole Monastrol Neuroactivesteroids(e.g.,allopregnanolone,cholesterol,THDOC) Niacin Niacinamide Nonbenzodiazepines(e.g.,β-carbolines(e.g.,abecarnil),cyclopyrrolones(e.g.,zopiclone),imidazopyridines(e.g.,zolpidem),pyrazolopyrimidines(e.g.,zaleplon)) Norfluoxetine Petrichloral Phenols(e.g.,propofol) Phenytoin Piperidinediones(e.g.,glutethimide) Propanidid Pyrazolopyridines(e.g.,etazolate) Quinazolinones(e.g.,methaqualone) Retigabine(ezogabine) ROD-188 Skullcapconstituents(e.g.,baicalin) Stiripentol Sulfonylalkanes(e.g.,sulfonmethane(sulfonal)) Topiramate Valerianconstituents(e.g.,valerenicacid) Volatiles/gases(e.g.,chloralhydrate,chloroform,diethylether,paraldehyde,sevoflurane) Antagonists:Bicuculline Coriamyrtin Dihydrosecurinine Gabazine(SR-95531) Hydrastine Hyenachin(mellitoxin) PHP-501 Pitrazepin Securinine Sinomenine SR-42641 SR-95103 Thiocolchicoside Tutin Negativemodulators:1,3M1B 3M2B 11-Ketoprogesterone 17-Phenylandrostenol α5IA(LS-193,268) β-CCB β-CCE β-CCM β-CCP β-EMGBL Anabolicsteroids Amiloride Anisatin β-Lactams(e.g.,penicillins,cephalosporins,carbapenems) Basmisanil Bemegride Bicyclicphosphates(TBPS,TBPO,IPTBO) BIDN Bilobalide Bupropion CHEB Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142(ZK-31906) Fiproles(e.g.,fipronil) Flavonoids(e.g.,amentoflavone,oroxylinA) Flumazenil Fluoroquinolones(e.g.,ciprofloxacin) Flurothyl Furosemide Golexanolone Iomazenil(123I) IPTBO Isopregnanolone(sepranolone) L-655,708 Laudanosine Leptazol Lindane MaxiPost Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Nonsteroidalantiandrogens(e.g.,apalutamide,bicalutamide,enzalutamide,flutamide,nilutamide) Oenanthotoxin Pentylenetetrazol(pentetrazol) Phenylsilatrane Picrotoxin(i.e.,picrotin,picrotoxininanddihydropicrotoxinin) Pregnenolonesulfate Propybicyphat PWZ-029 Radequinil Ro15-4513 Ro19-4603 RO4882224 RO4938581 Sarmazenil SCS Suritozole TB-21007 TBOB TBPS TCS-1105 Terbequinil TETS Thujone U-93631 Zinc ZK-93426 GABAA-ρ Agonists:BL-1020 CACA CAMP Homohypotaurine GABA GABOB Ibotenicacid Isoguvacine Muscimol N4-Chloroacetylcytosinearabinoside Picamilon Progabide TACA TAMP Thiomuscimol Tolgabide Positivemodulators:Allopregnanolone Alphaxolone ATHDOC Lanthanides Antagonists:(S)-2-MeGABA (S)-4-ACPBPA (S)-4-ACPCA 2-MeTACA 3-APMPA 4-ACPAM 4-GBA cis-3-ACPBPA CGP-36742(SGS-742) DAVA Gabazine(SR-95531) Gaboxadol(THIP) I4AA Isonipecoticacid Loreclezole P4MPA P4S SKF-97541 SR-95318 SR-95813 TPMPA trans-3-ACPBPA ZAPA Negativemodulators:5α-Dihydroprogesterone Bilobalide Loreclezole Picrotoxin(picrotin,picrotoxinin) Pregnanolone ROD-188 THDOC Zinc MetabotropicGABAB Agonists:1,4-Butanediol 3-APPA 4-Fluorophenibut Aceburicacid Arbaclofen Arbaclofenplacarbil Baclofen BL-1020 GABA Gabamide GABOB GBL GHB GHBAL GHV GVL Isovaline Lesogaberan Phenibut Picamilon Progabide Sodiumoxybate SKF-97,541 SL75102 Tolgabide Tolibut Positivemodulators:ADX-71441 BHF-177 BHFF BSPP CGP-7930 CGP-13501 GS-39783 rac-BHFF KK-92A Antagonists:2-Hydroxysaclofen CGP-35348 CGP-46381 CGP-52432 CGP-54626 CGP-55845 CGP-64213 DAVA Homotaurine(tramiprosate,3-APS) Phaclofen Saclofen SCH-50911 SKF-97541 Negativemodulators:Compound14 Seealso Receptor/signalingmodulators GABAAreceptorpositivemodulators GABAmetabolism/transportmodulators vteGrowthfactorreceptormodulatorsAngiopoietin Agonists:Angiopoietin1 Angiopoietin4 Antagonists:Angiopoietin2 Angiopoietin3 Kinaseinhibitors:Altiratinib CE-245677 Rebastinib Antibodies:Evinacumab(againstangiopoietin3) Nesvacumab(againstangiopoietin2) CNTF Agonists:Axokine CNTF Dapiclermin EGF(ErbB)EGF(ErbB1/HER1) Agonists:Amphiregulin Betacellulin EGF(urogastrone) Epigen Epiregulin Heparin-bindingEGF-likegrowthfactor(HB-EGF) Murodermin Nepidermin Transforminggrowthfactoralpha(TGFα) Kinaseinhibitors:Afatinib Agerafenib Brigatinib Canertinib Dacomitinib Erlotinib Gefitinib Grandinin Icotinib Lapatinib Neratinib Osimertinib Vandetanib WHI-P154 Antibodies:Cetuximab Depatuxizumab Depatuxizumabmafodotin Futuximab Imgatuzumab Matuzumab Necitumumab Nimotuzumab Panitumumab Zalutumumab ErbB2/HER2 Agonists:Unknown/none Antibodies:Ertumaxomab Pertuzumab Trastuzumab Trastuzumabderuxtecan Trastuzumabduocarmazine Trastuzumabemtansine Kinaseinhibitors:Afatinib Lapatinib Mubritinib Neratinib Tucatinib ErbB3/HER3 Agonists:Neuregulins(heregulins)(1,2,6(neuroglycanC)) Antibodies:Duligotumab Patritumab Seribantumab ErbB4/HER4 Agonists:Betacellulin Epigen Heparin-bindingEGF-likegrowthfactor(HB-EGF) Neuregulins(heregulins)(1,2,3,4,5(tomoregulin,TMEFF)) FGFFGFR1 Agonists:Ersofermin FGF(1,2(bFGF),3,4,5,6,8,10(KGF2),20) Repifermin Selpercatinib Trafermin Velafermin FGFR2 Agonists:Ersofermin FGF(1,2(bFGF),3,4,5,6,7(KGF),8,9,10(KGF2),17,18,22) Palifermin Repifermin Selpercatinib Sprifermin Trafermin Antibodies:Aprutumab Aprutumabixadotin Kinaseinhibitors:Infigratinib FGFR3 Agonists:Ersofermin FGF(1,2(bFGF),4,8,9,18,23) Selpercatinib Sprifermin Trafermin Antibodies:Burosumab(againstFGF23) FGFR4 Agonists:Ersofermin FGF(1,2(bFGF),4,6,8,9,19) Trafermin Unsorted Agonists:FGF15/19 HGF(c-Met) Agonists:Fosgonimeton Hepatocytegrowthfactor Potentiators:Dihexa(PNB-0408) Kinaseinhibitors:Altiratinib AM7 AMG-458 Amuvatinib BMS-777607 Cabozantinib Capmatinib Crizotinib Foretinib Golvatinib INCB28060 JNJ-38877605 K252a MK-2461 PF-04217903 PF-2341066 PHA-665752 SU-11274 Tivantinib Volitinib Antibodies:Emibetuzumab Ficlatuzumab Flanvotumab Onartuzumab Rilotumumab Telisotuzumab Telisotuzumabvedotin IGFIGF-1 Agonists:des(1-3)IGF-1 Insulin-likegrowthfactor-1(somatomedinC) IGF-1LR3 Insulin-likegrowthfactor-2(somatomedinA) Insulin Mecasermin Mecaserminrinfabate Kinaseinhibitors:BMS-754807 Linsitinib NVP-ADW742 NVP-AEW541 OSl-906 Antibodies:AVE-1642 Cixutumumab Dalotuzumab Figitumumab Ganitumab Robatumumab R1507 Teprotumumab Xentuzumab(againstIGF-1andIGF-2) IGF-2 Agonists:Insulin-likegrowthfactor-2(somatomedinA) Antibodies:Dusigitumab Xentuzumab(againstIGF-1andIGF-2) Others Bindingproteins:IGFBP(1,2,3,4,5,6,7) Cleavageproducts/derivativeswithunknowntarget:Glypromate(GPE,(1-3)IGF-1) Trofinetide LNGF(p75NTR) Agonists:BDNF BNN-20 BNN-27 Cenegermin DHEA DHEA-S NGF NT-3 NT-4 Antagonists:ALE-0540 Dexamethasone EVT-901(SAR-127963) Testosterone Antibodies:AgainstNGF:ABT-110(PG110) ASP-6294 Fasinumab Frunevetmab Fulranumab MEDI-578 Ranevetmab Tanezumab Aptamers:AgainstNGF:RBM-004 Decoyreceptors:LEVI-04(p75NTR-Fc) PDGF Agonists:Becaplermin Platelet-derivedgrowthfactor(A,B,C,D) Kinaseinhibitors:Agerafenib Avapritinib Axitinib Crenolanib Imatinib Lenvatinib Masitinib Motesanib Nintedanib Pazopanib Radotinib Quizartinib Ripretinib Sunitinib Sorafenib Toceranib Antibodies:Olaratumab Ramucirumab Tovetumab RET(GFL)GFRα1 Agonists:Glialcellline-derivedneurotrophicfactor(GDNF) Liatermin Kinaseinhibitors:Vandetanib GFRα2 Agonists:Neurturin(NRTN) Kinaseinhibitors:Vandetanib GFRα3 Agonists:Artemin(ARTN) Kinaseinhibitors:Vandetanib GFRα4 Agonists:Persephin(PSPN) Kinaseinhibitors:Vandetanib Unsorted Kinaseinhibitors:Agerafenib SCF(c-Kit) Agonists:Ancestim Stemcellfactor Kinaseinhibitors:Agerafenib Axitinib Dasatinib Imatinib Masitinib Nilotinib Pazopanib Quizartinib Sorafenib Sunitinib Toceranib TGFβ Seehereinstead. TrkTrkA Agonists:Amitriptyline BNN-20 BNN-27 Cenegermin DHEA DHEA-S Gambogicamide NGF Tavilermide Antagonists:ALE-0540 Dexamethasone FX007 Testosterone Negativeallostericmodulators:VM-902A Kinaseinhibitors:Altiratinib AZD-6918 CE-245677 CH-7057288 DS-6051 Entrectinib GZ-389988 K252a Larotrectinib Lestaurtinib Milciclib ONO-4474 ONO-5390556 PLX-7486 Rebastinib SNA-120(pegylatedK252a)) Antibodies:AgainstTrkA:GBR-900;AgainstNGF:ABT-110(PG110) ASP-6294 Fasinumab Frunevetmab Fulranumab MEDI-578 Ranevetmab Tanezumab Aptamers:AgainstNGF:RBM-004 Decoyreceptors:ReN-1820(TrkAd5) TrkB Agonists:3,7-DHF 3,7,8,2'-THF 4'-DMA-7,8-DHF 7,3'-DHF 7,8-DHF 7,8,2'-THF 7,8,3'-THF Amitriptyline BDNF BNN-20 Deoxygedunin Deprenyl Diosmetin DMAQ-B1 HIOC LM22A-4 N-Acetylserotonin NT-3 NT-4 Norwogonin(5,7,8-THF) R7 R13 TDP6 Antagonists:ANA-12 CyclotraxinB Gossypetin(3,5,7,8,3',4'-HHF) Ligands:DHEA Kinaseinhibitors:Altiratinib AZD-6918 CE-245677 CH-7057288 DS-6051 Entrectinib GZ-389988 K252a Larotrectinib Lestaurtinib ONO-4474 ONO-5390556 PLX-7486 TrkC Agonists:BNN-20 DHEA NT-3 Kinaseinhibitors:Altiratinib AZD-6918 CE-245677 CH-7057288 DS-6051 Entrectinib GZ-389988 K252a Larotrectinib Lestaurtinib ONO-4474 ONO-5390556 PLX-7486 VEGF Agonists:Placentalgrowthfactor(PGF) Ripretinib Telbermin VEGF(A,B,C,D(FIGF)) Allostericmodulators:CyclotraxinB Kinaseinhibitors:Agerafenib Altiratinib Axitinib Cabozantinib Cediranib Lapatinib Lenvatinib Motesanib Nintedanib Pazopanib Pegaptanib Rebastinib Regorafenib Semaxanib Sorafenib Sunitinib Toceranib Tivozanib Vandetanib WHI-P154 Antibodies:Alacizumabpegol Bevacizumab Icrucumab Ramucirumab Ranibizumab Decoyreceptors:Aflibercept Others Additionalgrowthfactors:Adrenomedullin Colony-stimulatingfactors(seehereinstead) Connectivetissuegrowthfactor(CTGF) Ephrins(A1,A2,A3,A4,A5,B1,B2,B3) Erythropoietin(seehereinstead) Glucose-6-phosphateisomerase(GPI;PGI,PHI,AMF) Gliamaturationfactor(GMF) Hepatoma-derivedgrowthfactor(HDGF) Interleukins/T-cellgrowthfactors(seehereinstead) Leukemiainhibitoryfactor(LIF) Macrophage-stimulatingprotein(MSP;HLP,HGFLP) Midkine(NEGF2) Migration-stimulatingfactor(MSF;PRG4) Oncomodulin Pituitaryadenylatecyclase-activatingpeptide(PACAP) Pleiotrophin Renalase Thrombopoietin(seehereinstead) Wntsignalingproteins Additionalgrowthfactorreceptormodulators:Cerebrolysin(neurotrophinmixture) vteIonotropicglutamatereceptormodulatorsAMPAR Agonists:Mainsiteagonists:5-Fluorowillardiine Acromelicacid(acromelate) AMPA BOAA Domoicacid Glutamate Ibotenicacid Proline Quisqualicacid Willardiine;Positiveallostericmodulators:Aniracetam BIIB-104(PF-04958242) Cyclothiazide CX-516 CX-546 CX-614 Farampator(CX-691,ORG-24448) CX-717 CX-1739 CX-1942 Diazoxide Hydrochlorothiazide(HCTZ) IDRA-21 LY-392098 LY-395153 LY-404187 LY-451646 LY-503430 Mibampator(LY-451395) Nooglutyl ORG-26576 Oxiracetam PEPA Piracetam Pramiracetam S-18986 Tulrampator(S-47445,CX-1632) Antagonists:ACEA-1011 ATPO Becampanel Caroverine CNQX Dasolampanel DNQX Fanapanel(MPQX) GAMS Kaitocephalin Kynurenicacid Kynurenine Licostinel(ACEA-1021) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel;Negativeallostericmodulators:Barbiturates(e.g.,pentobarbital,sodiumthiopental) Cyclopropane Enflurane Ethanol(alcohol) Evansblue GYKI-52466 GYKI-53655 Halothane Irampanel Isoflurane Perampanel Pregnenolonesulfate Sevoflurane Talampanel;Unknown/unsortedantagonists:Minocycline KAR Agonists:Mainsiteagonists:5-Bromowillardiine 5-Iodowillardiine Acromelicacid(acromelate) AMPA ATPA Domoicacid Glutamate Ibotenicacid Kainicacid LY-339434 Proline Quisqualicacid SYM-2081;Positiveallostericmodulators:Cyclothiazide Diazoxide Enflurane Halothane Isoflurane Antagonists:ACEA-1011 CNQX Dasolampanel DNQX GAMS Kaitocephalin Kynurenicacid Licostinel(ACEA-1021) LY-382884 NBQX NS102 Selurampanel Tezampanel Theanine Topiramate UBP-302;Negativeallostericmodulators:Barbiturates(e.g.,pentobarbital,sodiumthiopental) Enflurane Ethanol(alcohol) Evansblue NS-3763 Pregnenolonesulfate NMDAR Agonists:Mainsiteagonists:AMAA Aspartate Glutamate Homocysteicacid(L-HCA) Homoquinolinicacid Ibotenicacid NMDA Proline Quinolinicacid Tetrazolylglycine Theanine;Glycinesiteagonists:β-Fluoro-D-alanine ACBD ACC(ACPC) ACPD AK-51 Apimostinel(NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine Milacemide Neboglamine(nebostinel) Rapastinel(GLYX-13) Sarcosine;Polyaminesiteagonists:Neomycin Spermidine Spermine;Otherpositiveallostericmodulators:24S-Hydroxycholesterol DHEA(prasterone) DHEAsulfate(prasteronesulfate) Epipregnanolonesulfate Plazinemdor Pregnenolonesulfate SAGE-201 SAGE-301 SAGE-718 Antagonists:Competitiveantagonists:AP5(APV) AP7 CGP-37849 CGP-39551 CGP-39653 CGP-40116 CGS-19755 CPP Kaitocephalin LY-233053 LY-235959 LY-274614 MDL-100453 Midafotel(d-CPPene) NPC-12626 NPC-17742 PBPD PEAQX Perzinfotel PPDA SDZ-220581 Selfotel;Glycinesiteantagonists:4-Cl-KYN(AV-101) 5,7-DCKA 7-CKA ACC ACEA-1011 ACEA-1328 Apimostinel(NRX-1074) AV-101 Carisoprodol CGP-39653 CNQX D-Cycloserine DNQX Felbamate Gavestinel GV-196771 Harkoseride Kynurenicacid Kynurenine L-689560 L-701324 Licostinel(ACEA-1021) LU-73068 MDL-105519 Meprobamate MRZ2/576 PNQX Rapastinel(GLYX-13) ZD-9379;Polyaminesiteantagonists:Arcaine Co101676 Diaminopropane Diethylenetriamine HuperzineA Putrescine;Uncompetitiveporeblockers(mostlydizocilpinesite):2-MDP 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP 8A-PDHQ 18-MC α-Endopsychosin Alaproclate Alazocine(SKF-10047) Amantadine Aptiganel Argiotoxin-636 Arketamine ARL-12495 ARL-15896-AR ARL-16247 Budipine Coronaridine Delucemine(NPS-1506) Dexoxadrol Dextrallorphan Dextromethadone Dextromethorphan Dextrorphan Dieticyclidine Diphenidine Dizocilpine Ephenidine Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan Levomilnacipran Levorphanol Loperamide Memantine Methadone Methorphan Methoxetamine Methoxphenidine Milnacipran Morphanol NEFA Neramexane Nitromemantine Noribogaine Norketamine Orphenadrine PCPr PD-137889 Pethidine(meperidine) Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Rimantadine Rolicyclidine Sabeluzole Tabernanthine Tenocyclidine Tiletamine Tramadol;Ifenprodil(NR2B)siteantagonists: Besonprodil Buphenine(nylidrin) CO-101244(PD-174494) Eliprodil Haloperidol Isoxsuprine Radiprodil(RGH-896) Rislenemdaz(CERC-301,MK-0657) Ro8-4304 Ro25-6981 Safaprodil Traxoprodil(CP-101606);NR2A-selectiveantagonists:MPX-004 MPX-007 TCN-201 TCN-213;Cations:Hydrogen Magnesium Zinc;Alcohols/volatileanesthetics/related:Benzene Butane Chloroform Cyclopropane Desflurane Diethylether Enflurane Ethanol(alcohol) Halothane Hexanol Isoflurane Methoxyflurane Nitrousoxide Octanol Sevoflurane Toluene Trichloroethane Trichloroethanol Trichloroethylene Urethane Xenon Xylene;Unknown/unsortedantagonists:ARR-15896 Bumetanide Caroverine Conantokin D-αAA Dexanabinol Flufenamicacid Flupirtine FPL-12495 FR-115427 Furosemide Hodgkinsine Ipenoxazone(MLV-6976) MDL-27266 Metaphit Minocycline MPEP Niflumicacid Pentamidine Pentamidineisethionate Piretanide Psychotridine Transcrocetin(saffron) Unsorted:Allostericmodulators:AGN-241751 Seealso:Receptor/signalingmodulators Metabotropicglutamatereceptormodulators Glutamatemetabolism/transportmodulators vteSigmareceptormodulatorsσ1 Agonists:3-PPP 4-PPBP 5-MeO-DMT Alazocine(SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRP Cloperastine Cocaine Cutamesine(SA-4503) Cyclazocine Dehydroepiandrosterone(DHEA)(prasterone) Dehydroepiandrosteronesulfate(DHEA-S)(prasteronesulfate) Dextrallorphan Dextromethorphan(DXM) Dextrorphan(DXO) Dimemorfan Dimethyltryptamine(DMT) Ditolylguanidine(DTG) Donepezil Eliprodil Escitalopram Fabomotizole(afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine(JO-1784) IPAB Ketamine L-687384 MDMA(midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone NeuropeptideY Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine(carbetapentane) PRE-084 Pregnenolone Pregnenolonesulfate Pridopidine Racemethorphan(methorphan) Racemorphan(morphanol) UMB-23 UMB-82 Antagonists:3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802(BMS-181100) CM-156 Dup-734 E-5842 E-52862(S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine(EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole(BW-234U) Sertraline SR-31742A Allostericmodulators:Phenytoin;Positive:Methylphenylpiracetam SOMCL-668 Unknown/unsorted:3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPT DPT Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A σ2 Agonists:3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine(DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA(midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine(Lu28-179) UKH-1114 Antagonists:AC-927 BD-1008 BD-1067 CM-156 CT-1812 LR-172 MIN-101 Panamesine(EMD-57455) SAS-0132 Unknown/unsorted:3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPT DPT Ibogaine Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMA UMB-23 UMB-82 W-18 Unsorted Agonists:Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists:AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allostericmodulators:SKF-83959 Unknown/unsorted:18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine(chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin(St.John'swort) Fluphenazine Gevotroline(WY-47384) Mepyramine(pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL82.0715 SR-31747A Tiospirone(BMY-13859) Venlafaxine Seealso:Receptor/signalingmodulators vteTRPchannelmodulatorsTRPAActivators 4-Hydroxynonenal 4-Oxo-2-nonenal 4,5-EET 12S-HpETE 15-Deoxy-Δ12,14-prostaglandinJ2 α-Sanshool(ginger,Sichuanandmeleguetapeppers) Acrolein Allicin(garlic) Allylisothiocyanate(mustard,radish,horseradish,wasabi) AM404 ASP-7663 Bradykinin Cannabichromene(cannabis) Cannabidiol(cannabis) Cannabigerol(cannabis) Cinnamaldehyde(cinnamon) CRgas(dibenzoxazepine;DBO) CSgas(2-chlorobenzalmalononitrile) Cuminaldehyde(cumin) Curcumin(turmeric) Dehydroligustilide(celery) Diallyldisulfide Dicentrine(Linderaspp.) Farnesylthiosalicylicacid Formalin Gingerols(ginger) HepoxilinA3 HepoxilinB3 Hydrogenperoxide Icilin Isothiocyanate JT-010 Ligustilide(celery,Angelicaacutiloba) Linalool(Sichuanpepper,thyme) Methylglyoxal Methylsalicylate(wintergreen) N-Methylmaleimide Nicotine(tobacco) Oleocanthal(oliveoil) Paclitaxel(Pacificyew) Paracetamol(acetaminophen) PF-4840154 Phenacylchloride Polygodial(Dorrigopepper) Shogaols(ginger,Sichuanandmeleguetapeppers) Teargases Tetrahydrocannabinol(cannabis) Tetrahydrocannabiorcol ThiopropanalS-oxide(onion) Umbellulone(Umbellulariacalifornica) WIN55,212-2 Blockers A-967079 AM-0902 Dehydroligustilide(celery) HC-030031 Nicotine(tobacco) PF-04745637 Rutheniumred TRPCActivators Adhyperforin(StJohn'swort) Diacylglycerol GSK1702934A Hyperforin(StJohn'swort) SubstanceP Blockers DCDPC DHEA-S Flufenamicacid GSK417651A GSK2293017A Meclofenamicacid N-(p-Amylcinnamoyl)anthranilicacid Niflumicacid Pregnenolonesulfate Progesterone Pyr3 Tolfenamicacid TRPMActivators ADP-ribose BCTC Calcium(intracellular) CIM-0216 Cold CoolactP CoolingAgent10 Eucalyptol(eucalyptus) FrescolatMGA FrescolatML Geraniol Hydroxycitronellal Icilin Linalool Menthol(mint) PMD38 Pregnenolonesulfate Rutamarin(Rutagraveolens) Steviolglycosides(e.g.,stevioside)(Steviarebaudiana) Sweettastants(e.g.,glucose,fructose,sucrose;indirectly) Thio-BCTC WS-12 Blockers AMG-333 Capsazepine Clotrimazole DCDPC Elismetrep Flufenamicacid Meclofenamicacid Mefenamicacid N-(p-Amylcinnamoyl)anthranilicacid Nicotine(tobacco) Niflumicacid Ononetin PF-05105679 RQ-00203078 Rutheniumred Rutamarin(Rutagraveolens) Tolfenamicacid TPPO TRPM4-IN-5 TRPMLActivators EVP21 MK6-83 ML-SA1 ML2-SA1 PI(3,5)P2 SF-22 SN-2 Blockers ML-SI3 PI(4,5)P2 TRPPActivators Triptolide(Tripterygiumwilfordii) Blockers Rutheniumred TRPVActivators 2-APB 5',6'-EET 9-HODE 9-oxoODE 12S-HETE 12S-HpETE 13-HODE 13-oxoODE 20-HETE α-Sanshool(ginger,Sichuanandmeleguetapeppers) Allicin(garlic) AM404 Anandamide Bisandrographolide(Andrographispaniculata) Camphor(camphorlaurel,rosemary,camphorweed,Africanbluebasil,camphorbasil) Cannabidiol(cannabis) Cannabidivarin(cannabis) Capsaicin(chilipepper) Carvacrol(oregano,thyme,pepperwort,wildbergamot,others) DHEA Diacylglycerol Dihydrocapsaicin(chilipepper) Estradiol Eugenol(basil,clove) Evodiamine(Euodiaruticarpa) Gingerols(ginger) GSK1016790A Heat HepoxilinA3 HepoxilinB3 Homocapsaicin(chilipepper) Homodihydrocapsaicin(chilipepper) Incensole(incense) Lysophosphatidicacid LowpH(acidicconditions) Menthol(mint) N-Arachidonoyldopamine N-Oleoyldopamine N-Oleoylethanolamide Nonivamide(PAVA)(PAVAspray) Nordihydrocapsaicin(chilipepper) Paclitaxel(Pacificyew) Paracetamol(acetaminophen) Phenylacetylrinvanil Phorbolesters(e.g.,4α-PDD) Piperine(blackpepper,longpepper) Polygodial(Dorrigopepper) Probenecid Protons RhTx Rutamarin(Rutagraveolens) Resiniferatoxin(RTX)(Euphorbiaresinifera/pooissonii) Shogaols(ginger,Sichuanandmeleguetapeppers) Tetrahydrocannabivarin(cannabis) Thymol(thyme,oregano) Tinyatoxin(Euphorbiaresinifera/pooissonii) Tramadol Vanillin(vanilla) Zucapsaicin Blockers α-Spinasterol(Vernoniatweediana) AMG-517 AMG-9810 Asivatrep BCTC Cannabigerol(cannabis) Cannabigerolicacid(cannabis) Cannabigerovarin(cannabis) Cannabinol(cannabis) Capsazepine DCDPC DHEA DHEA-S Flufenamicacid GRC-6211 HC-067047 Lanthanum Mavatrep Meclofenamicacid N-(p-Amylcinnamoyl)anthranilicacid NGD-8243 Niflumicacid Pregnenolonesulfate RN-1734 RN-9893 Rutheniumred SB-366791 SB-705498 Tivanisiran Tolfenamicacid TRPV3-74a Seealso:Receptor/signalingmodulators•Ionchannelmodulators vteXenobiotic-sensingreceptormodulatorsCAR Agonists:6,7-Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole Cyclophosphamide Cypermethrin DHEA(prasterone) Efavirenz Ellagicacid Griseofulvin Methoxychlor Mifepristone Nefazodone Nevirapine Nicardipine Octicizer Permethrin Phenobarbital Phenytoin Pregnanedione(5β-dihydroprogesterone) Reserpine TCPOBOP Telmisartan Tolnaftate Troglitazone Valproicacid Antagonists:3,17β-Estradiol 3α-Androstanol 3α-Androstenol 3β-Androstanol 17-Androstanol AITC Ethinylestradiol Meclizine NigramideJ Okadaicacid PK-11195 S-07662 T-0901317 PXR Agonists:17α-Hydroxypregnenolone 17α-Hydroxyprogesterone Δ4-Androstenedione Δ5-Androstenediol Δ5-Androstenedione AA-861 Allopregnanediol Allopregnanedione(5α-dihydroprogesterone) Allopregnanolone(brexanolone) Alpha-Lipoicacid Ambrisentan AMI-193 Amlodipinebesylate Antimycotics Artemisinin Aurothioglucose Bileacids Bithionol Bosentan Bumecaine Cafestol Cephaloridine Cephradine Chlorpromazine Ciglitazone Clindamycin Clofenvinfos Chloroxine Clotrimazole Colforsin Corticosterone Cyclophosphamide Cyproteroneacetate Demecolcine Dexamethasone DHEA(prasterone) DHEA-S(prasteronesulfate) Dibunatesodium Diclazuril Dicloxacillin Dimercaprol Dinaline Docetaxel Docusatecalcium Dodecylbenzenesulfonicacid Dronabinol Droxidopa Eburnamonine Ecopipam Enzacamene EpothiloneB Erythromycin Famprofazone Febantel Felodipine Fenbendazole Fentanyl Flucloxacillin Fluorometholone Griseofulvin Guggulsterone Haloprogin Hetacillinpotassium Hyperforin Hypericumperforatum(StJohn'swort) Indinavirsulfate Lasalocidsodium Levothyroxine Linolenicacid LOE-908 Loratadine Lovastatin Meclizine Metacycline Methylprednisolone Metyrapone Mevastatin Mifepristone Nafcillin Nicardipine Nicotine Nifedipine Nilvadipine Nisoldipine Norelgestromin Omeprazole Orlistat Oxatomide Paclitaxel Phenobarbital Piperine Plicamycin Prednisolone Pregnanediol Pregnanedione(5β-dihydroprogesterone) Pregnanolone Pregnenolone Pregnenolone16α-carbonitrile Proadifen Progesterone Quingestrone Reserpine Reversetriiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine SR-12813 Suberoylanilide Sulfisoxazole Suramin Tacrolimus Tenylidone Terconazole Testosteroneisocaproate Tetracycline Thiamylalsodium Thiothixene Thonzoniumbromide Tianeptine Troglitazone Troleandomycin Tropanyl3,5-dimethulbenzoate Zafirlukast Zeranol Antagonists:Ketoconazole Sesamin Seealso Receptor/signalingmodulators 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