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Chemical compound
Epiestriol Trade names Actriol, Arcagynil, Klimadoral Other names Epioestriol; 16β-Epiestriol; 16-Epiestriol; 16β-Hydroxy-17β-estradiol Routes of By mouth Drug class Estrogen
(8R ,9S ,13S ,14S ,16S ,17R )-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a ]phenanthrene-3,16,17-triol
CAS Number PubChem CID ChemSpider UNII ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.008.126 Formula C 18 H 24 O 3 Molar mass −1 3D model (JSmol )
CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17+,18+/m1/s1
Key:PROQIPRRNZUXQM-ZMSHIADSSA-N
Epiestriol (INN Tooltip International Nonproprietary Name ) (brand namesActriol ,Arcagynil ,Klimadoral ), orepioestriol (BAN Tooltip British Approved Name ), also known as16β-epiestriol or simply16-epiestriol as well as16β-hydroxy-17β-estradiol ,is a minor and weakendogenous estrogen ,and the 16β-epimer ofestriol (which is 16α-hydroxy-17β-estradiol).[1] [2] acne .[1] anti-inflammatory properties withoutglycogenic activity orimmunosuppressive effects, an interesting finding that is in contrast to conventional anti-inflammatory steroids likehydrocortisone (aglucocorticoid ).[3] [4]
Relative affinities (%) of epiestriol and related steroids[5] [6] [7] [8]
Compound
PR Tooltip Progesterone receptor AR Tooltip Androgen receptor ER Tooltip Estrogen receptor GR Tooltip Glucocorticoid receptor MR Tooltip Mineralocorticoid receptor SHBG Tooltip Sex hormone-binding globulin CBG Tooltip Corticosteroid binding globulin
Estradiol 2.6
7.9
100
0.6
0.13
8.7
<0.1
Alfatradiol <1
<1
15
<1
<1
?
?
Estriol <1
<1
15
<1
<1
?
?
16β-Epiestriol
<1
<1
20
<1
<1
?
?
17α-Epiestriol <1
<1
31
<1
<1
?
?
Values are percentages (%). Referenceligands (100%) wereprogesterone for thePR Tooltip progesterone receptor ,testosterone for theAR Tooltip androgen receptor ,E2 ER Tooltip estrogen receptor ,DEXA Tooltip dexamethasone for theGR Tooltip glucocorticoid receptor ,aldosterone for theMR Tooltip mineralocorticoid receptor ,DHT Tooltip dihydrotestosterone forSHBG Tooltip sex hormone-binding globulin ,andcortisol forCBG Tooltip Corticosteroid-binding globulin .
^a b Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 ^ Labhart A (6 December 2012).Clinical Endocrinology: Theory and Practice ISBN 978-3-642-96158-8 ^ Latman NS, Kishore V, Bruot BC (June 1994). "16-epiestriol: an anti-inflammatory steroid without glycogenic activity".Journal of Pharmaceutical Sciences .83 (6): 874–7.doi :10.1002/jps.2600830623 .PMID 9120824 . ^ Miller E, Bates R, Bjorndahl J, Allen D, Burgio D, Bouma C, Stoll J, Latman N (November 1998). "16-Epiestriol, a novel anti-inflammatory nonglycogenic steroid, does not inhibit IFN-gamma production by murine splenocytes".Journal of Interferon & Cytokine Research .18 (11): 921–5.doi :10.1089/jir.1998.18.921 .PMID 9858313 . ^ Raynaud JP, Ojasoo T, Bouton MM, Philibert D (1979)."Receptor Binding as a Tool in the Development of New Bioactive Steroids" .Drug Design .pp. 169–214.doi :10.1016/B978-0-12-060308-4.50010-X .ISBN 9780120603084 ^ Ojasoo T, Raynaud JP (November 1978)."Unique steroid congeners for receptor studies" .Cancer Research .38 (11 Pt 2): 4186–98.PMID 359134 . ^ Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors".Journal of Steroid Biochemistry .27 (1–3): 255–69.doi :10.1016/0022-4731(87)90317-7 .PMID 3695484 . ^ Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, Labrie F, Mornon JP (January 1980). "Steroid hormone receptors and pharmacology".Journal of Steroid Biochemistry .12 :143–57.doi :10.1016/0022-4731(80)90264-2 .PMID 7421203 .
Estrogens
ER Tooltip Estrogen receptor agonists
Steroidal: Alfatradiol Certainandrogens /anabolic steroids (e.g.,testosterone ,testosterone esters ,methyltestosterone ,metandienone ,nandrolone esters ) (via estrogenic metabolites)
Certainprogestins (e.g.,norethisterone ,noretynodrel ,etynodiol diacetate ,tibolone )
Clomestrone Cloxestradiol acetate Conjugated estriol Conjugated estrogens Epiestriol Epimestrol Esterified estrogens Estetrol † Estradiol Estradiol esters (e.g.,estradiol acetate ,estradiol benzoate ,estradiol cypionate ,estradiol enanthate ,estradiol undecylate ,estradiol valerate ,polyestradiol phosphate ,estradiol ester mixtures (Climacteron ))Estramustine phosphate Estriol Estriol esters (e.g.,estriol succinate ,polyestriol phosphate )Estrogenic substances Estrone Estrone esters
Ethinylestradiol #
Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Nilestriol Prasterone (dehydroepiandrosterone; DHEA)
Promestriene Quinestradol Quinestrol Progonadotropins
Antiestrogens
ER Tooltip Estrogen receptor antagonistsSERMs Tooltip selective estrogen receptor modulators /SERDs Tooltip selective estrogen receptor downregulators )Aromatase inhibitors Antigonadotropins
Androgens /anabolic steroids (e.g.,testosterone ,testosterone esters ,nandrolone esters ,oxandrolone ,fluoxymesterone )D2 receptor antagonists (prolactin releasers) (e.g.,domperidone ,metoclopramide ,risperidone ,haloperidol ,chlorpromazine ,sulpiride )GnRH agonistsleuprorelin ,goserelin )GnRH antagonistscetrorelix ,elagolix )Progestogens (e.g.,chlormadinone acetate ,cyproterone acetate ,gestonorone caproate ,hydroxyprogesterone caproate ,medroxyprogesterone acetate ,megestrol acetate ) Others
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 andesters ,methyltestosterone ,metandienone (methandrostenolone) ,nandrolone andesters ,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
