{{위키데이터 속성 추적}}
{{Drugbox
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 458286647
| IUPAC_name = (8''R'',9''S'',13''S'',14''S'',17''R'')-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6''H''-cyclopenta[''a'']phenanthrene-3,17-diol
| image = Ethinylestradiol.svg
| width = 235px
| image2 = Ethinylestradiol molecule ball.png
| width2 = 235px

<!--Clinical data-->
| pronounce = {{IPAc-en|ˌ|ɛ|θ|ᵻ|n|ᵻ|l|ˌ|ɛ|s|t|r|ə|ˈ|d|aɪ|.|əl}}
| tradename = numerous
| synonyms = ethynylestradiol; ethinyl estradiol; ethinyl oestradiol; EE; EE2; 17α-ethynylestradiol; 17α-ethynylestra-1,3,5(10)-triene-3,17β-diol; NSC-10973ref name="Elks2014">{{서적 인용| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA522|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=522–}}</ref>
| Drugs.com = {{drugs.com|international|ethinylestradiol}}
| MedlinePlus = a604032
| pregnancy_category = X ([[미국]])
| licence_EU = yes
| legal_status = Rx-only
| routes_of_administration = • [[경구 투여]] ([[알약]])<br />• [[피부경유]] ([[피임 패치]])<br />• [[질내 투여]] ([[질내 고리]])
| class = [[에스트로젠 (의약품)|에스트로젠]]

<!--Pharmacokinetic data-->
| bioavailability = 38–48%<ref name="pmid2256522"/><ref name="pmid22468839">{{저널 인용| vauthors = Fruzzetti F, Trémollieres F, Bitzer J | title = An overview of the development of combined oral contraceptives containing estradiol: focus on estradiol valerate/dienogest | journal = Gynecological Endocrinology | volume = 28 | issue = 5 | pages = 400–408 | date = May 2012 | pmid = 22468839 | pmc = 3399636 | doi = 10.3109/09513590.2012.662547 }}</ref><ref name="pmid8842581">{{저널 인용| vauthors = Fotherby K | title = Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy | journal = Contraception | volume = 54 | issue = 2 | pages = 59–69 | date = August 1996 | pmid = 8842581 | doi = 10.1016/0010-7824(96)00136-9 }}</ref>
| protein_bound = 97–98% ([[사람 혈청 알부민|알부민]]에 결합;<ref name="(Firm)Inc2005">{{서적 인용|author1=Facts and Comparisons (Firm)|author2=Ovid Technologies, Inc|title=Drug Facts and Comparisons 2005: Pocket Version|url=https://books.google.com/books?id=zumzLgzj1CsC&q=ethinyl+estradiol+albumin|year=2005|publisher=Facts and Comparisons|isbn=978-1-57439-179-4|page=121}}</ref>{{abbrlink|SHBG|성호르몬 결합 글로불린}}에 결합하지 않음)<ref name="Micromedex2003">{{서적 인용|author=Micromedex|title=USP DI 2003: Drug Information for Healthcare Professionals|url=https://books.google.com/books?id=zEzWtsVl-KgC|date=1 January 2003|publisher=Thomson Micromedex|isbn=978-1-56363-429-1|pages=1253, 1258, 1266}}</ref>
| metabolism = [[간]] (주로 [[CYP3A4]])<ref name="HughesWaters2016">{{서적 인용| vauthors = Hughes CL, Waters MD |title=Translational Toxicology: Defining a New Therapeutic Discipline|url=https://books.google.com/books?id=5qPWCwAAQBAJ&pg=PA73|date=23 March 2016|publisher=Humana Press|isbn=978-3-319-27449-2|pages=73–}}</ref>
| metabolites = • [[Ethinylestradiol sulfate]]<ref name="pmid16112947" /><ref name="OettelSchillinger2012" /><br />• Others<ref name="pmid16112947" /><ref name="OettelSchillinger2012" />
| elimination_half-life = 7–36 hours<ref name="HughesWaters2016" /><ref name="pmid2256522">{{저널 인용| vauthors = Goldzieher JW, Brody SA | title = Pharmacokinetics of ethinyl estradiol and mestranol | journal = American Journal of Obstetrics and Gynecology | volume = 163 | issue = 6 Pt 2 | pages = 2114–2119 | date = December 1990 | pmid = 2256522 | doi = 10.1016/0002-9378(90)90550-Q }}</ref><ref name="pmid23375353">{{저널 인용| 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="Shellenberger1986">{{서적 인용| vauthors = Shellenberger TE |chapter=Pharmacology of estrogens|year=1986|pages=393–410|doi=10.1007/978-94-009-4145-8_36|title=The Climacteric in Perspective|isbn=978-94-010-8339-3|quote=Ethinyl estradiol is a synthetic and comparatively potent estrogen. As a result of the alkylation in 17-C position it is not a substrate for 17β dehydrogenase, an enzyme which transforms natural estradiol-17β to the less potent estrone in target organs.}}</ref>
| excretion = [[대변]]: 62%<ref name="pmid23375353" /><br />[[소변]]: 38%<ref name="pmid23375353" />

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 57-63-6
| ATC_prefix = G03
| ATC_suffix = CA01
| ATC_supplemental = {{ATC|L02|AA03}}
| PubChem = 5991
| IUPHAR_ligand = 7071
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00977
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5770
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 423D2T571U
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00554
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4903
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 691

<!--Chemical data-->
| C=20 | H=24 | O=2
| SMILES = Oc1cc4c(cc1)[C@H]3CC[C@]2([C@@H](CC[C@]2(C#C)O)[C@@H]3CC4)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BFPYWIDHMRZLRN-SLHNCBLASA-N
| melting_point = 182
| melting_high = 184
}}
<!-- Definition and medical uses -->
'''에티닐에스트라다이올'''({{llang|en|ethinylestradiol}}, '''EE''')은 [[프로게스틴]]과 함께 [[피임약]]에 널리 사용되는 [[에스트로젠]] 약물이다.<ref name="pmid16112947">{{저널 인용| 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="OettelSchillinger2012">{{서적 인용| vauthors = Oettel M, Schillinger E |title=Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen|url=https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA369|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-60107-1|pages=4,10,15,165,247–248,276–291,363–408,424,514,540,543,581|quote=The binding affinity of EE2 for the estrogen receptor is similar to that of estradiol. [...] During daily intake, the EE2 levels increase up to a steady state which is reached after about 1 week.}}</ref> '''17α-에티닐에스트라다이올'''({{llang|en|17α-ethinylestradiol}}), '''17-''R''-에티닐에스트라다이올'''({{llang|en|17-''R''-ethinylestradiol}})이라고도 한다. 과거에 에티닐에스트라다이올은 [[갱년기]] [[증상]], [[부인과|부인과 질환]] 및 특정 [[호르몬 민감성 암]]의 치료와 같은 다양한 적응증에 널리 사용되었다. 일반적으로 [[경구 투여]]하지만 [[경피 패치|패치]] 및 [[질내고리]]로 사용된다.<ref name="pmid16112947" /><ref name="Drugs@FDA">{{웹 인용| title = Drugs@FDA: FDA Approved Drug Products | publisher = United States Food and Drug Administration | access-date = 22 December 2016 | url = http://www.accessdata.fda.gov/scripts/cder/daf/}}</ref>

== 같이 보기 ==
* [[에스트라다이올]]

== 각주 ==
{{각주}}

== 더 읽을거리 ==
{{참고 자료 시작}}
* {{서적 인용| vauthors = Oettel M, Schillinger E |title=Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen|url=https://books.google.com/books?id=wBvyCAAAQBAJ|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-60107-1|pages=4,10,15,165,247–248,276–291,363–408,424,514,540,543,581}}
* {{저널 인용| 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 }}
* {{저널 인용| 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 }}
* {{저널 인용| vauthors = Mattison DR, Karyakina N, Goodman M, LaKind JS | title = Pharmaco- and toxicokinetics of selected exogenous and endogenous estrogens: a review of the data and identification of knowledge gaps | journal = Critical Reviews in Toxicology | volume = 44 | issue = 8 | pages = 696–724 | date = September 2014 | pmid = 25099693 | doi = 10.3109/10408444.2014.930813 | s2cid = 11212469 }}
{{참고 자료 끝}}

{{전거 통제}}

[[분류:CYP1A2 억제제]]
[[분류:에티닐 화합물]]
[[분류:항생식샘자극호르몬]]
[[분류:에스트란]]
[[분류:GPER 작용제]]
[[분류:간독소]]
[[분류:호르몬성 항암제]]
[[분류:호르몬 피임법]]
[[분류:사람의 약물 대사산물]]
[[분류:프로락틴 방출제]]
[[분류:페놀류]]
[[분류:합성 에스트로겐]]