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ent-Estradiol

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Chemical compound

Pharmaceutical compound

Ent-Estradiol
Clinical data

Other names	ent-E2; 1-Estradiol; 1-E2
Drug class	Estrogen
Identifiers
IUPAC name (8S,9R,13R,14R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number	3736-22-9^Y
PubChemCID	667515
UNII	VW299DJ6U7
CompTox Dashboard(EPA)	DTXSID60912332
Chemical and physical data
Formula	C₁₈H₂₄O₂
Molar mass	272.388 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@@]12CC[C@@H]3[C@@H]([C@H]1CC[C@H]2O)CCC4=C3C=CC(=C4)O
InChI InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m0/s1 Key:VOXZDWNPVJITMN-QXDIGNSFSA-N

ent-Estradiol (ent-E2), or1-estradiol (1-E2), is anestrogen and the 1-enantiomorph ofestradiol.^[1]^[2]^[3] It is a so-called "short-acting" or "impeded" estrogen, similarly toestriol,17α-estradiol, anddimethylstilbestrol.^[1]^[2]^[3]

References

[edit]

^^a ^bEdgren RA, Jones RC (September 1969). "An anti-estradiol effect of ent-estradiol-17beta (1-estradiol)".Steroids.14 (3):335–41.doi:10.1016/0039-128x(69)90021-x.PMID 5821989.
^^a ^bTerenius L, Ljungkvist I (1972). "Aspects on the mode of action of antiestrogens and antiprogestogens".Gynecol Invest.3 (1):96–107.doi:10.1159/000301746.PMID 4347201.
^^a ^bTerenius L (June 1971). "The Allen-Doisy test for estrogens reinvestigated".Steroids.17 (6):653–61.doi:10.1016/0039-128x(71)90081-x.PMID 5104534.

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists	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 Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g.,testosterone andesters,methyltestosterone,metandienone (methandrostenolone),nandrolone andesters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Cloxestradiol acetate Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent-Estradiol Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol Estradiol esters Lipoidal estradiol Polyestradiol phosphate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol esters Polyestriol phosphate Estrofurate Estrogenic substances Estromustine Estrone Estrone esters Estrone methyl ether Estropipate Etamestrol (eptamestrol) Ethinylandrostenediol Ethandrostate Ethinylestradiol Ethinylestradiol 3-benzoate Ethinylestradiol sulfonate Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate 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 Allenolic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Butestrol Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol Dienestrol diacetate Diethylstilbestrol Diethylstilbestrol esters Dimestrol (dianisylhexene) Dimethylstilbestrol Doisynoestrol (fenocycline) Doisynolic acid Efavirenz Elacestrant ERB-196 (WAY-202196) Erteberel (SERBA-1, LY-500307) Estrobin (DBE) Fenestrel FERb 033 Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol esters ICI-85966 (Stilbostat) M2613 meso-Butestrol meso-Hexestrol Mestilbol Methallenestril Methestrol Methestrol dipropionate 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,biochanin A,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) Lavender oil 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) Resorcylic acid lactones (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) Synthetic xenoestrogens (e.g.,alkylphenols,bisphenols (e.g.,BPA,BPF,BPS),DDT,parabens,PBBs,PHBA,phthalates,PCBs) Others (e.g.,agnuside,rotundifuran)
Mixed (SERMsTooltip Selective estrogen receptor modulators)	2-Phenylbenzofuran 2-Phenyl-1-benzothiophene 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 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 Miproxifene phosphate MRL-37 Nafoxidine Nitromifene NNC 45-0095 NNC 45-0320 NNC 45-0781 NNC 45-1506 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 Cytestrol acetate 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 Oxabicycloheptene sulfonate Phenytoin PHTPP Prochloraz RU-39411 RU-58668 SS1020 TAS-108 (SR-16234) ZB716 ZK-164015 ZK-191703 Coregulator-binding modulators:ERX-11 Noncompetitive inhibitors:Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT,o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide 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

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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