Estriol (medication)のソースを表示

{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{About|estriol as a medication|its role as a hormone|Estriol}}
{{Drugbox
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 477167082
| IUPAC_name = (8''R'',9''S'',13''S'',14''S'',16''R'',17''R'')-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[''a'']phenanthrene-3,16,17-triol
| image = Estriol.svg
| width = 250
| alt = 
| image2 = Estriol molecule ball.png
| width2 = 235
| alt2 = 

<!--Clinical data-->
| pronounce = {{IPAc-en|ˈ|ɛ|s|t|r|i|ɒ|l|,_|-|t|r|aɪ|ɒ|l}}<ref name="Dictionary.com">[http://www.dictionary.com/browse/estriol Estriol]. [[Dictionary.com]].</ref> <br />{{respell|ESS|TREE|ohl}}<ref name="Dictionary.com" />
| tradename = Ovestin, others<ref name="IndexNominum2000" /><ref name="Drugs.com" />
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| routes_of_administration = [[Oral administration|By mouth]], [[vaginal administration|vaginal]], [[intramuscular injection]]<ref name="pmid16112947" /><ref name="OettelSchillinger2012" /><ref name="pmid11600867" />
| class = [[Estrogen (medication)|Estrogen]]
| ATC_prefix = G03
| ATC_suffix = CA04
| ATC_supplemental = <br />{{ATC|G03|CC06}}

| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = 
| legal_UK = 
| legal_US = 
| legal_status = Rx-only

<!--Pharmacokinetic data-->
| bioavailability = [[Oral administration|Oral]]: ~1–2%<ref name="pmid16112947" /><ref name="pmid11600867" /><br />[[Vaginal administration|Vaginal]]: ~10–20%<ref name="OettelSchillinger2012" /><ref name="pmid16112947" /><ref name="pmid11600867" />
| protein_bound = 92%:<ref name="pmid16112947" /><br />• [[Human serum albumin|Albumin]]: 91%<ref name="pmid16112947" /><br />• {{abbrlink|SHBG|Sex hormone-binding globulin}}: 1%<ref name="pmid16112947" /><br />• Free: 8%<ref name="pmid16112947" />
| metabolism = [[Liver]], [[intestine]]s ([[conjugation (biochemistry)|conjugation]] ([[glucuronidation]], [[sulfation]]), [[oxidation]], [[hydroxylation]])<ref name="pmid16112947" />
| metabolites = • [[Estriol 16α-glucuronide]]<ref name="MuseyKirdani1973" /><ref name="OettelSchillinger2012" /><br />• [[Estriol 3-glucuronide]]<ref name="MuseyKirdani1973" /><ref name="OettelSchillinger2012" /><br />• [[Estriol 3-sulfate]]<ref name="MuseyKirdani1973" /><ref name="OettelSchillinger2012" /><br />• [[Estriol 3-sulfate 16α-glucuronide|Estriol 3-sulfate 16α-gluc.]]<ref name="MuseyKirdani1973" /><ref name="OettelSchillinger2012" /><br />• [[16α-Hydroxyestrone]]<ref name="pmid16112947" /><ref name="Dörwald2013" /><br />• Others (minor)<ref name="pmid16112947" />
| elimination_half-life = Oral: 5–10 hours<ref name="Wentz1988">{{cite book| vauthors = Wentz AC |title=Gynecologic Endocrinology and Infertility for the House Officer|url=https://books.google.com/books?id=3I5sAAAAMAAJ|date=January 1988|publisher=Williams & Wilkins|isbn=978-0-683-08931-8|quote=Estriol is considered a short-acting estrogen with a half-life of 5 hours.}}</ref><ref name="Dörwald2013">{{cite book| vauthors = Dörwald FZ | chapter = Steroids |title=Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds| chapter-url=https://books.google.com/books?id=YTeY9ZEfNccC&pg=PA486|date=4 February 2013|publisher=John Wiley & Sons|isbn=978-3-527-64565-7|pages=486–}}</ref><br />{{abbrlink|IM|Intramuscular injection}}: 1.5–5.3 hours (as {{abbr|E3|estriol (unconjugated)}})<ref name="OettelSchillinger2012" /><br />{{abbrlink|IV|Intravenous injection}}: 20&nbsp;minutes (as {{abbr|E3|estriol (unconjugated)}})<ref name="pmid18464021">{{cite journal | vauthors = Visser M, Holinka CF, Coelingh Bennink HJ | title = First human exposure to exogenous single-dose oral estetrol in early postmenopausal women | journal = Climacteric | volume = 11 | issue = Suppl 1 | pages = 31–40 | date = 2008 | pmid = 18464021 | doi = 10.1080/13697130802056511 | s2cid = 23568599 }}</ref><ref name="UniversityofCalifornia1986">{{cite book|title=Applied Biochemistry of Clinical Disorders|edition=2nd |url=https://books.google.com/books?id=as1NAQAAIAAJ|year=1986|publisher=University of California|isbn=978-0-397-50768-9|quote=Because its half-life is about 20 minutes, unconjugated estriol rapidly reflects changes in estriol production.}}</ref>
| excretion = [[Urine]]: >95% (as [[conjugation (biochemistry)|conjugate]]s)<ref name="pmid16112947" /><ref name="OettelSchillinger2012" />

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 50-27-1
| CAS_supplemental = <br />1306-04-3<br />514-68-1 ([[succinate]])
| PubChem = 5756
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04573
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5553
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FB33469R8E
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 27974
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C05141
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 193482
| IUPHAR_ligand = 2821
| synonyms = Oestriol; E3; 16α-Hydroxyestradiol; Estra-1,3,5(10)-triene-3,16α,17β-triol

<!--Chemical data-->
| C=18 | H=24 | O=3
| SMILES = Oc1cc3c(cc1)[C@H]2CC[C@@]4([C@@H](O)[C@H](O)C[C@H]4[C@@H]2CC3)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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 = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PROQIPRRNZUXQM-ZXXIGWHRSA-N

<!--Physical data-->
| melting_point = 82
| melting_high = 86
| melting_notes = (experimental)
| solubility = 0.119
}}
<!-- Definition and medical uses -->
'''Estriol''' ('''E3'''), sold under the brand name '''Ovestin''' among others, is an [[estrogen (medication)|estrogen]] medication and [[natural product|naturally occurring]] [[steroid hormone]] which is used in [[menopausal hormone therapy]].<ref name="pmid28622049">{{cite journal | vauthors = Rueda C, Osorio AM, Avellaneda AC, Pinzón CE, Restrepo OI | title = The efficacy and safety of estriol to treat vulvovaginal atrophy in postmenopausal women: a systematic literature review | journal = Climacteric | volume = 20 | issue = 4 | pages = 321–330 | date = August 2017 | pmid = 28622049 | doi = 10.1080/13697137.2017.1329291 | s2cid = 407950 }}</ref><ref name="pmid16112947">{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | issue = Suppl 1 | pages = 3–63 | date = August 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 }}</ref><ref name="pmid11600867" /><ref name="Zutshi2005" /> It is also used in [[veterinary medicine]] as '''Incurin''' to treat [[urinary incontinence]] due to [[estrogen deficiency]] in dogs.<ref name="EttingerFeldman2017" /><ref name="Boothe2011" /><ref name="BonaguraTwedt2008" /><ref name="Papich2015" /> The medication is taken [[oral administration|by mouth]] in the form of [[tablet (pharmacy)|tablet]]s, as a [[cream (pharmaceutical)|cream]] that is [[topical administration|applied to the skin]], as a cream or [[pessary]] that is [[vaginal administration|applied in the vagina]], and by [[intramuscular injection|injection into muscle]].<ref name="pmid16112947" /><ref name="OettelSchillinger2012" /><ref name="pmid11600867" />

<!-- Side effects and mechanism -->
Estriol is well-[[tolerability|tolerated]] and produces relatively few [[adverse effect]]s.<ref name="pmid28622049" /><ref name="pmid28375935" /> Side effects may include [[breast tenderness]], [[vaginal discomfort]] and [[vaginal discharge|discharge]], and [[endometrial hyperplasia]].<ref name="pmid28622049" /><ref name="pmid28375935" /> Estriol is a [[natural product|naturally occurring]] and [[bioidentical hormone therapy|bioidentical]] estrogen, or an [[agonist]] of the [[estrogen receptor]], the [[biological target]] of [[estrogen]]s like [[endogenous]] [[estradiol]].<ref name="pmid16112947" /> It is an atypical and relatively weak estrogen, with much lower [[potency (pharmacology)|potency]] than [[estradiol (medication)|estradiol]].<ref name="pmid16112947" /><ref name="pmid11600867" /><ref name="Becker2001" /> When present continuously at adequate concentrations however, estriol produces full [[estrogen (medication)|estrogenic]] effects similarly to estradiol.<ref name="pmid6356176a" /><ref name="Clark_1984" />

<!-- History, society, and culture -->
Estriol was first discovered in 1930,<ref name="Josimovich2013" /><ref name="SartorelliJohns2013" /> and was introduced for medical use shortly thereafter.<ref name="pmid13567043" /><ref name="pmid18744783" /> [[Estriol ester]]s such as [[estriol succinate]] are also used.<ref name="pmid16112947" /><ref name="pmid28375935" /><ref name="Drugs.com" /> Although it is less commonly employed than other estrogens like estradiol and [[conjugated estrogens]], estriol is widely available for medical use in [[Europe]] and elsewhere throughout the world.<ref name="pmid16112947" /><ref name="IndexNominum2000" /><ref name="Drugs.com" /><ref name="pmid11600867">{{cite journal | vauthors = Taylor M | title = Unconventional estrogens: estriol, biest, and triest | journal = Clinical Obstetrics and Gynecology | volume = 44 | issue = 4 | pages = 864–879 | date = December 2001 | pmid = 11600867 | doi = 10.1097/00003081-200112000-00024 | s2cid = 27098486 }}</ref>

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