Epiestriolのソースを表示

{{Short description|Chemical compound}}
{{Distinguish|episterol}}
{{Other uses|epiestriol (set index)}}
{{Drugbox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| IUPAC_name = (8''R'',9''S'',13''S'',14''S'',16''S'',17''R'')-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[''a'']phenanthrene-3,16,17-triol
| image = Epiestriol.svg
| width = 225px

<!--Clinical data-->
| tradename = Actriol, Arcagynil, Klimadoral
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = [[Oral administration|By mouth]]
| class = [[Estrogen (medication)|Estrogen]]

<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
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<!--Identifiers-->
| CAS_number_Ref =
| CAS_number = 547-81-9
| CAS_supplemental =
| ATC_prefix =
| ATC_suffix =
| PubChem = 68929
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 62155
| UNII = 8XZ32LI44K
| ChEMBL = 1908074
| synonyms = Epioestriol; 16β-Epiestriol; 16-Epiestriol; 16β-Hydroxy-17β-estradiol

<!--Chemical data-->
| C=18 | H=24 | O=3
| SMILES = CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
| StdInChI_Ref =
| StdInChI = 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
| StdInChIKey_Ref =
| StdInChIKey = PROQIPRRNZUXQM-ZMSHIADSSA-N
}}

'''Epiestriol''' ({{abbrlink|INN|International Nonproprietary Name}}) (brand names '''Actriol''', '''Arcagynil''', '''Klimadoral'''), or '''epioestriol''' ({{abbrlink|BAN|British Approved Name}}), also known as '''16β-epiestriol''' or simply '''16-epiestriol,''' as well as '''16β-hydroxy-17β-estradiol''', is a minor and weak [[endogenous]] [[estrogen (medication)|estrogen]], and the 16β-[[epimer]] of [[estriol]] (which is 16α-hydroxy-17β-estradiol).<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA899|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=899–}}</ref><ref name="Labhart2012">{{cite book | vauthors = Labhart A |title=Clinical Endocrinology: Theory and Practice|url=https://books.google.com/books?id=DAgJCAAAQBAJ&pg=PA522|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-96158-8|pages=522–}}</ref> Epiestriol is (or has previously been) used clinically in the treatment of [[acne]].<ref name="Elks2014" /> In addition to its estrogenic actions, epiestriol has been found to possess significant [[anti-inflammatory]] properties without [[glycogenesis|glycogenic]] activity or [[immunosuppressive]] effects, an interesting finding that is in contrast to conventional anti-inflammatory steroids such as [[hydrocortisone]] (a [[glucocorticoid]]).<ref name="pmid9120824">{{cite journal | vauthors = Latman NS, Kishore V, Bruot BC | title = 16-epiestriol: an anti-inflammatory steroid without glycogenic activity | journal = Journal of Pharmaceutical Sciences | volume = 83 | issue = 6 | pages = 874–7 | date = June 1994 | pmid = 9120824 | doi = 10.1002/jps.2600830623 }}</ref><ref name="pmid9858313">{{cite journal | vauthors = Miller E, Bates R, Bjorndahl J, Allen D, Burgio D, Bouma C, Stoll J, Latman N | title = 16-Epiestriol, a novel anti-inflammatory nonglycogenic steroid, does not inhibit IFN-gamma production by murine splenocytes | journal = Journal of Interferon & Cytokine Research | volume = 18 | issue = 11 | pages = 921–5 | date = November 1998 | pmid = 9858313 | doi = 10.1089/jir.1998.18.921 }}</ref>

{| class="wikitable center sortable mw-collapsible mw-collapsed" style="width:600px; text-align:left; margin-left:auto; margin-right:auto; border:none;"
|+ class="nowrap" | Relative affinities (%) of epiestriol and related steroids<ref name="RaynaudOjasoo1979">{{cite book | vauthors = Raynaud JP, Ojasoo T, Bouton MM, Philibert D  | title = Drug Design| chapter = Receptor Binding as a Tool in the Development of New Bioactive Steroids|year=1979|pages=169–214|doi=10.1016/B978-0-12-060308-4.50010-X| isbn = 9780120603084|chapter-url=https://books.google.com/books?id=bhAlBQAAQBAJ&pg=PA169}}</ref><ref name="pmid359134">{{cite journal | vauthors = Ojasoo T, Raynaud JP | title = Unique steroid congeners for receptor studies | journal = Cancer Research | volume = 38 | issue = 11 Pt 2 | pages = 4186–98 | date = November 1978 | pmid = 359134 | url = http://cancerres.aacrjournals.org/content/38/11_Part_2/4186.short }}</ref><ref name="pmid3695484">{{cite journal | vauthors = Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP | title = Towards the mapping of the progesterone and androgen receptors | journal = Journal of Steroid Biochemistry | volume = 27 | issue = 1–3 | pages = 255–69 | date = 1987 | pmid = 3695484 | doi = 10.1016/0022-4731(87)90317-7 }}</ref><ref name="pmid7421203">{{cite journal | vauthors = Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, Labrie F, Mornon JP | title = Steroid hormone receptors and pharmacology | journal = Journal of Steroid Biochemistry | volume = 12 | pages = 143–57 | date = January 1980 | pmid = 7421203 | doi = 10.1016/0022-4731(80)90264-2 }}</ref>
|-
! Compound || {{abbrlink|PR|Progesterone receptor}} || {{abbrlink|AR|Androgen receptor}} || {{abbrlink|ER|Estrogen receptor}} || {{abbrlink|GR|Glucocorticoid receptor}} || {{abbrlink|MR|Mineralocorticoid receptor}} || {{abbrlink|SHBG|Sex hormone-binding globulin}} || {{abbrlink|CBG|Corticosteroid binding globulin}}
|-
| [[Estradiol (medication)|Estradiol]] || 2.6 || 7.9 || 100 || 0.6 || 0.13 || 8.7 || <0.1
|-
| [[Alfatradiol]] || <1 || <1 || 15 || <1 || <1 || ? || ?
|-
| [[Estriol (medication)|Estriol]] || <1 || <1 || 15 || <1 || <1 || ? || ?
|-
| 16β-Epiestriol || <1 || <1 || 20 || <1 || <1 || ? || ?
|-
| [[17α-Epiestriol]] || <1 || <1 || 31 || <1 || <1 || ? || ?
|- class="sortbottom"
| colspan="10" style="width: 1px;" | Values are percentages (%). Reference [[ligand (biochemistry)|ligand]]s (100%) were [[progesterone (medication)|progesterone]] for the {{abbrlink|PR|progesterone receptor}}, [[testosterone (medication)|testosterone]] for the {{abbrlink|AR|androgen receptor}}, [[estradiol (medication)|{{abbr|E2|estradiol}}]] for the {{abbrlink|ER|estrogen receptor}}, {{abbrlink|DEXA|dexamethasone}} for the {{abbrlink|GR|glucocorticoid receptor}}, [[aldosterone]] for the {{abbrlink|MR|mineralocorticoid receptor}}, {{abbrlink|DHT|dihydrotestosterone}} for {{abbrlink|SHBG|sex hormone-binding globulin}}, and [[hydrocortisone|cortisol]] for {{abbrlink|CBG|Corticosteroid-binding globulin}}.
|}

== See also ==
* [[17α-Epiestriol]]
* [[16β,17α-Epiestriol]]
* [[Epimestrol]]
* [[Mytatrienediol]]

== References ==
{{Reflist}}

{{Steroid hormones}}
{{Acne agents}}
{{Estrogens and antiestrogens}}
{{Estrogen receptor modulators}}

[[Category:Anti-acne preparations]]
[[Category:Anti-inflammatory agents]]
[[Category:Estranes]]
[[Category:Estrogens]]
[[Category:Hormones of the hypothalamus-pituitary-gonad axis]]
[[Category:Sex hormones]]


{{Steroid-stub}}
{{Genito-urinary-drug-stub}}