Estradiol benzoateのソースを表示

{{Short description|Chemical compound}}{{Use dmy dates|date=December 2023}}{{cs1 config|name-list-style=vanc}}{{Use PMID reference names|date=December 2023}}
{{Drugbox
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| IUPAC_name = [(8''R'',9''S'',13''S'',14''S'',17''S'')-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[''a'']phenanthren-3-yl] benzoate
| image = Estradiol benzoate.svg
| width = 250px
| image2 = Estradiol benzoate molecule ball.png
| width2 = 250px

<!--Clinical data-->
| pronounce = {{IPAc-en|ˌ|ɛ|s|t|r|ə|ˈ|d|aɪ|oʊ|l|_|ˈ|b|ɛ|n|z|oʊ|eɪ|t}}<br />{{respell|ES|trə|DY|ohl|_|BEN|zoh|ayt}}
| tradename = Agofollin Depot, Ben-Ovocylin, Benzofoline, Dimenformon, Ovocyclin M, Progynon-B, many others
| 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 = Rx-only
| routes_of_administration = [[Intramuscular injection]], [[subcutaneous injection]], [[vaginal administration|vaginal]]
| class = [[Estrogen (medication)|Estrogen]]; [[Estrogen ester]]

<!--Pharmacokinetic data-->
| bioavailability = {{abbr|IM|Intramuscular injection}}: High<ref name="pmid7169965">{{cite journal | vauthors = Düsterberg B, Nishino Y | title = Pharmacokinetic and pharmacological features of oestradiol valerate | journal = Maturitas | volume = 4 | issue = 4 | pages = 315–324 | date = December 1982 | pmid = 7169965 | doi = 10.1016/0378-5122(82)90064-0 }}</ref>
| protein_bound = Estradiol: ~98% (to [[human serum albumin|albumin]] and {{abbrlink|SHBG|sex hormone-binding globulin}})<ref name="pmid23375353">{{cite journal | vauthors = Stanczyk FZ, Archer DF, Bhavnani BR | title = Ethinyl estradiol and 17β-estradiol in combined oral contraceptives: pharmacokinetics, pharmacodynamics and risk assessment | journal = Contraception | volume = 87 | issue = 6 | pages = 706–727 | date = June 2013 | pmid = 23375353 | doi = 10.1016/j.contraception.2012.12.011 }}</ref><ref name="Falcone-2007">{{Cite book | vauthors = Falcone T, Hurd WH |url=https://books.google.com/books?id=fOPtaEIKvcIC&pg=PA22 |title=Clinical Reproductive Medicine and Surgery  |publisher=Elsevier Health Sciences |year=2007 |isbn=978-0-323-03309-1 |pages=22,362,388}}</ref>
| metabolism = [[Bond cleavage|Cleavage]] via [[esterase]]s in the [[liver]], [[blood]], and [[tissue (biology)|tissue]]s<ref name="Oettel-2012" /><ref name="pmid16112947" />
| metabolites = [[Estradiol (medication)|Estradiol]], [[benzoic acid]], and [[metabolite]]s of estradiol<ref name="Oettel-2012" /><ref name="pmid16112947" />
| elimination_half-life = {{abbr|IM|Intramuscular injection}}: 48–120 hrs (2–5 days)<ref name="Runnebaum-2013">{{Cite book | vauthors = Runnebaum B, Rabe T |url=https://books.google.com/books?id=mBF9BwAAQBAJ&pg=PA86 |title=Gynäkologische Endokrinologie und Fortpflanzungsmedizin: Band 1: Gynäkologische Endokrinologie  |date=17 April 2013 |publisher=Springer-Verlag |isbn=978-3-662-07635-4 |pages=86–}}</ref>
| duration_of_action = {{abbr|IM|Intramuscular injection}} (0.3–1.7 mg): 2–3 days<ref name="Buchsbaum-2012" /><ref name="NNR1949e" /><br />{{abbr|IM|Intramuscular injection}} (5 mg): 4–6 days<ref name="pmid7389356" /><ref name="Knörr-2013">{{Cite book | vauthors = Knörr K, Knörr-Gärtner H, Beller FK, Lauritzen C |url=https://books.google.com/books?id=OjvMBgAAQBAJ&pg=PA508 |title=Lehrbuch der Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion  |date=8 March 2013 |publisher=Springer-Verlag |isbn=978-3-662-00526-2 |pages=508–}}</ref><ref name="Labhart-2012" />
| excretion = [[Urine]]

<!-- Identifiers -->
| CAS_number_Ref = 
| CAS_number = 50-50-0
| CAS_supplemental = 
| ATC_prefix = G03
| ATC_suffix = CA03
| ATC_supplemental = 
| PubChem = 222757
| IUPHAR_ligand = 
| DrugBank_Ref = 
| DrugBank = DB13953
| ChemSpiderID_Ref = 
| ChemSpiderID = 193412
| UNII = 1S4CJB5ZGN
| KEGG = D01953
| ChEBI = 77006
| ChEMBL = 282575
| synonyms = EB; E2B; Oestradiol benzoate; 17β-Estradiol-3-benzoate; NSC-9566; Benzhormovarine, Difollisterol, Follicormon, Follidimyl, Follidrinbensoat, Oestro-Vitis, Oestroform

<!--Chemical data-->
| C=25 | H=28 | O=3
| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)C5=CC=CC=C5
| StdInChI_Ref = 
| StdInChI = 1S/C25H28O3/c1-25-14-13-20-19-10-8-18(28-24(27)16-5-3-2-4-6-16)15-17(19)7-9-21(20)22(25)11-12-23(25)26/h2-6,8,10,15,20-23,26H,7,9,11-14H2,1H3/t20-,21-,22+,23+,25+/m1/s1
| StdInChIKey_Ref = 
| StdInChIKey = UYIFTLBWAOGQBI-BZDYCCQFSA-N
}}
<!-- Definition and medical uses -->
'''Estradiol benzoate''' ('''EB'''), sold under the brand name '''Progynon-B''' among others, is an [[estrogen (medication)|estrogen]] medication which is used in [[hormone replacement therapy|hormone therapy]] for [[menopausal symptoms]] and [[hypoestrogenism|low estrogen levels]] in women, in [[transgender hormone therapy (male-to-female)|hormone therapy]] for [[transgender women]], and in the treatment of [[gynecological disorder]]s.<ref name="NNR1949e" /><ref name="pmid13638626" /><ref name="Israel-2001" /> It is also used in the treatment of [[prostate cancer]] in men.<ref name="NNR1949e" /> Estradiol benzoate is used in [[veterinary medicine]] as well.<ref name="Drugs.com-Estradiol" /><ref name="IndexNominum2000" /> When used clinically, the medication is given by [[intramuscular injection|injection into muscle]] usually two to three times per week.<ref name="NNR1949e" /><ref name="pmid13638626" /><ref name="HumansOrganization2007">{{Cite book | author1 = IARC Working Group on the Evaluation of Carcinogenic Risks to Humans |url=https://books.google.com/books?id=aGDU5xibtNgC&pg=PA388 |title=Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy | author2 = World Health Organization | author3 = International Agency for Research on Cancer |publisher=World Health Organization |year=2007 |isbn=978-92-832-1291-1 |pages=388–}}</ref>

<!-- Side effects and mechanism -->
[[Side effect]]s of estradiol benzoate include [[breast tenderness]], [[breast enlargement]], [[nausea]], [[headache]], and [[water retention (medicine)|fluid retention]].<ref name="Ghosh-2010" /> Estradiol benzoate is an [[estrogen (medication)|estrogen]] and hence is an [[agonist]] of the [[estrogen receptor]], the [[biological target]] of [[estrogen]]s like [[estradiol]].<ref name="Oettel-2012" /><ref name="pmid16112947" /> It is an [[estrogen ester]] and a [[prodrug]] of [[estradiol (medication)|estradiol]] in the body.<ref name="Oettel-2012" /><ref name="pmid16112947" /> Because of this, it is considered to be a [[natural product|natural]] and [[bioidentical hormone replacement therapy|bioidentical]] form of estrogen.<ref name="Oettel-2012" />

<!-- History, society, and culture -->
Estradiol benzoate was discovered in 1933 and was introduced for medical use that same year.<ref name="Oettel-2012" /><ref name="pmid16746750" /><ref name="Kaufman-1933" /><ref name="Buschbeck-1934" /><ref name="Biskind-1935" /><ref name="Novak-1935" /><ref name="Kleemann-2014" /> It was the first [[estradiol ester]] to be discovered or marketed, and was one of the first estrogens to be used in medicine.<ref name="Raviña-2011">{{Cite book | vauthors = Raviña E, Kubinyi H |url=https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA175 |title=The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs  |date=16 May 2011 |publisher=John Wiley & Sons |isbn=978-3-527-32669-3 |page=175 |access-date=20 May 2012}}</ref> Along with [[estradiol dipropionate]], estradiol benzoate was among the most widely used esters of estradiol for many years following its introduction.<ref name="pmid14388061" /> However, in the 1950s, longer-acting estradiol esters that necessitated less frequent injections, such as [[estradiol valerate]] and [[estradiol cypionate]], were developed, and have since largely superseded estradiol benzoate.<ref name="pmid7389356">{{Cite journal |vauthors=Oriowo MA, Landgren BM, Stenström B, Diczfalusy E |date=April 1980 |title=A comparison of the pharmacokinetic properties of three estradiol esters |journal=Contraception |volume=21 |issue=4 |pages=415–24 |doi=10.1016/S0010-7824(80)80018-7 |pmid=7389356}}</ref> Nonetheless, estradiol benzoate remains widely available throughout the world.<ref name="IndexNominum2000" /> It is not available for medical use in the [[United States]], but is available there for use in veterinary medicine.<ref name="Drugs@FDA" /><ref name="Witherspoon-1994" />

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