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Chemical compound
16α-LE2
3,17β-Dihydroxy-16α,21-epoxy-19-nor-17α-pregna-1,3,5(10)-trien-21-one
CAS Number ChemSpider UNII Formula C 20 H 24 O 4 Molar mass −1 3D model (JSmol )
O=C1O[C@@]2([H])[C@]([C@@]3(C)CC[C@]4([H])C5=CC=C(C=C5CC[C@@]4([H])[C@]3([H])C2)O)(C1)O
InChI=InChI=1S/C20H24O4/c1-19-7-6-14-13-5-3-12(21)8-11(13)2-4-15(14)16(19)9-17-20(19,23)10-18(22)24-17/h3,5,8,14-17,21,23H,2,4,6-7,9-10H2,1H3/t14-,15-,16+,17-,19+,20+/m1/s1
Key:NLUGVTJBNRSIKH-UQZPWQSVSA-N
16α-LE2 , or 16α-lactone-estradiol , also known as 3,17β-dihydroxy-19-nor-17α-pregna-1,3,5-(10)-triene-21,16α-lactone , is a synthetic , steroidal estrogen featuring an estradiol core. It is a highly potent and selective agonist of the ERα that is used in scientific research to study the function of the ERα.[ 1] [ 2] potency in transactivation assays of the ERα relative to the ERβ and 70-fold preference in binding affinity for the ERα over the ERβ.[ 2]
In rodents, 16α-LE2 has no effect on ovarian follicle development, whereas the highly ERβ-selective agonist 8β-VE2 stimulates follicular growth and to a comparable extent as estradiol , indicating that the ERβ and not the ERα is involved in the effects of estrogen on ovarian follicles.[ 2] [ 3] uterine weight, whereas 8β-VE2 has no effect, indicating that the ERα and not the ERβ is involved in the effects of estrogen on the uterus.[ 2] rodent studies with estradiol, 16α-LE2, and 8β-VE2 that the positive, protective effects of estrogens on bone formation resorption and bone mineral density are mediated via the ERα, whereas the ERβ does not appear to be involved.[ 4]
^ Pakdel F, Kah O, Jégou B (31 March 2009). "Mechanisms of action of particular endocrine-disrupting chemicals" . In Shaw I (ed.). Endocrine-Disrupting Chemicals in Food . Elsevier. pp. 550–. ISBN 978-1-84569-574-3 ^ a b c d Hegele-Hartung C, Siebel P, Peters O, Kosemund D, Müller G, Hillisch A, et al. (April 2004). "Impact of isotype-selective estrogen receptor agonists on ovarian function" . Proceedings of the National Academy of Sciences of the United States of America . 101 (14): 5129–5134. Bibcode :2004PNAS..101.5129H . doi :10.1073/pnas.0306720101 PMC 387385 PMID 15037755 . ^ Binder K, Winuthayanon W, Hewitt SC, Couse JF, Korach KS (15 November 2014). "Steroid Receptors in the Uterus and Ovary" . In Plant TM, Zeleznik AJ (eds.). Knobil and Neill's Physiology of Reproduction . Academic Press. pp. 1150–. ISBN 978-0-12-397769-4 ^ Hertrampf T, Schleipen B, Velders M, Laudenbach U, Fritzemeier KH, Diel P (September 2008). "Estrogen receptor subtype-specific effects on markers of bone homeostasis" (PDF) . Molecular and Cellular Endocrinology . 291 (1–2): 104–108. doi :10.1016/j.mce.2008.03.003 . PMID 18433985 . S2CID 1774519 .
ER Tooltip 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 and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol
Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent -EstradiolEpiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol
Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol
Estrofurate Estrogenic substances Estromustine Estrone
Etamestrol (eptamestrol) Ethinylandrostenediol
Ethinylestradiol
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 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 ) MixedSERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
