Estrone (medication)のソースを表示

{{Short description|Estrogen medication}}
{{About|estrone as a medication|its role as a hormone|Estrone}}
{{Use dmy dates|date=August 2018}}
{{Drugbox
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 389314385
| IUPAC_name = (8''R'',9''S'',13''S'',14''S'')-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6''H''-cyclopenta[''a'']phenanthren-17-one
| image = Estron.svg
| width = 215px
| image2 = Estrone molecule ball.png
| width2 = 235px

<!--Clinical data-->
| tradename = Estragyn, Kestrin, Theelin, many others
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = Rx-only 
| legal_status = 
| routes_of_administration = [[Intramuscular injection]], [[vaginal administration|vaginal]], [[oral administration|by mouth]] (as {{abbrlink|E2/E1/E3|estradiol/estrone/estriol}} or as [[estrone sulfate (medication)|estrone sulfate]])<ref name="Martindale" /><ref name="GuoHahn2000" /><ref name="Speroff2015" /><ref name="HelmsQuan2006" /><ref name="pmid16112947" />
| class = [[Estrogen (medication)|Estrogen]]

<!--Pharmacokinetic data-->
| bioavailability = [[Oral administration|Oral]]: very low<ref name="MelmonCarruthers2000" />
| protein_bound = 96.0–98.0%:<ref name="pmid16112947" /><ref name="JamesonGroot2010" /><br />• [[Human serum albumin|Albumin]]: ~80%<br />• {{abbr|SHBG|sex hormone-binding globulin}}: ~16%<br />• Free: 2.0–4.0%
| metabolism = [[Liver]] (via [[hydroxylation]], [[sulfation]], [[glucuronidation]])<ref name="pmid16112947" />
| metabolites = • [[Estradiol (medication)|Estradiol]]<ref name="pmid16112947" /><br />• [[Estrone sulfate (medication)|Estrone sulfate]]<ref name="pmid16112947" /><br />• [[Estrone glucuronide]]<ref name="pmid16112947" /><br />• Others<ref name="pmid16112947" />
| elimination_half-life = {{abbrlink|IV|Intravenous injection}}: 20–30 minutes<ref name="pmid16112947" />
| excretion = [[Urine]]<ref name="pmid16112947" />

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 53-16-7
| ATC_prefix = G03
| ATC_suffix = CA07
| ATC_supplemental = <br />{{ATC|G03|CC04}}
| PubChem = 5870
| IUPHAR_ligand = 2818
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00655
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5660
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2DI9HA706A
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00067
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17263
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1405
| synonyms = Oestrone; E1; Follicular hormone; Folliculin; Folliculine; Follikulin; Theelin; Ketohydroxyestrin; Oxohydroxyestrin; 3-Hydroxyestra-1,3,5(10)-trien-17-one

<!--Chemical data-->
| C=18 | H=22 | O=2
| SMILES = O=C4[C@]3(CC[C@@H]2c1ccc(O)cc1CC[C@H]2[C@@H]3CC4)C
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = DNXHEGUUPJUMQT-CBZIJGRNSA-N

<!--Physical data-->
| melting_point = 254.5
}}
<!-- Definition and medical uses -->
'''Estrone''' ('''E1'''), sold under the brand names '''Estragyn''', '''Kestrin''', and '''Theelin''' among many others, is an [[estrogen (medication)|estrogen]] medication and [[natural product|naturally occurring]] [[steroid hormone]] which has been used in [[menopausal hormone therapy]] and for other indications.<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 | year = 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 | url = http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf}}</ref><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="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA407|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=407–}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA207|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=207–}}</ref><ref name="Martindale">{{cite book | veditors = Sweetman SC |chapter=Sex hormones and their modulators |title=Martindale: The Complete Drug Reference |edition=36th |year=2009 |page=2101 |publisher=Pharmaceutical Press |location=London|isbn=978-0-85369-840-1|url=https://www.medicinescomplete.com/mc/martindale/2009/9092-j.htm}}</ref><ref name="GuoHahn2000">{{cite book| vauthors = Guo JZ, Hahn DW, Wachter MP |title=Kirk-Othmer Encyclopedia of Chemical Technology|chapter=Hormones, Estrogens and Antiestrogens|year=2000|publisher=Wiley |doi=10.1002/0471238961.05192018072115.a01|isbn=0471238961}}</ref> It has been provided as an [[aqueous suspension]] or [[oil solution]] given by [[intramuscular injection|injection into muscle]] and as a [[vaginal estrogen|vaginal]] [[cream (pharmacy)|cream]] applied [[vaginal administration|inside of the vagina]].<ref name="Martindale" /><ref name="GuoHahn2000" /><ref name="Speroff2015">{{cite book | veditors = Speroff L | chapter = Women's Hormonal Health Issues | title = Blood and Marrow Transplant Handbook: Comprehensive Guide for Patient Care. |year=2015|pages=341–354|doi=10.1007/978-3-319-13832-9_28|isbn=978-3-319-13831-2 | last1 = Speroff | first1 = Leon }}</ref><ref name="HelmsQuan2006">{{cite book| vauthors = Vuong LK | chapter = Gynecological Disorders | veditors = Helms RA, Quan DJ |title=Textbook of Therapeutics: Drug and Disease Management| chapter-url=https://books.google.com/books?id=aVmRWrknaWgC&pg=PA397|year=2006|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-5734-8|pages=397–}}</ref> It can also be taken [[oral administration|by mouth]] as [[estradiol/estrone/estriol]] (brand name '''Hormonin''') and in the form of [[prodrug]]s like [[estropipate]] ([[estrone sulfate (medication)|estrone sulfate]]; brand name '''Ogen''') and [[conjugated estrogens]] (mostly estrone sulfate; brand name '''Premarin''').<ref name="Buchsbaum2012">{{cite book| vauthors = Quirk Jr JG, Wendel Jr GD | chapter = Biologic effects of natural and synthetic estrogens | veditors = Buchsbaum HJ |title=The Menopause| chapter-url = https://books.google.com/books?id=z0LuBwAAQBAJ&pg=PA64|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4612-5525-3|pages=60, 62, 64}}</ref><ref name="GuoHahn2000" /><ref name="pmid16112947" />

<!-- Side effects and mechanism -->
[[Side effect]]s of estrogens like estrone include [[breast tenderness]], [[breast enlargement]], [[headache]], [[nausea]], [[water retention (medicine)|fluid retention]], and [[edema]], among others.<ref name="pmid16112947" /> Estrone 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 a relatively weak estrogen, with much lower [[biological activity|activity]] than [[estradiol (medication)|estradiol]].<ref name="pmid16112947" /> However, estrone is [[biotransformation|converted]] in the body into estradiol, which provides most or all of its estrogenic [[potency (pharmacology)|potency]].<ref name="pmid16112947" /><ref name="FishmanMartucci1980" /> As such, estrone is a [[prodrug]] of estradiol.<ref name="pmid16112947" />

<!-- History, society, and culture -->
Estrone was first discovered in 1929, and was introduced for medical use shortly thereafter.<ref name="Bullough1995" /><ref name="pmid18744783" /><ref name="Watkins2007" /> Although it has been used clinically in the past, estrone has largely been discontinued and is mostly no longer marketed.<ref name="IndexNominum2000" /><ref name="Drugs.com" />

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