炔雌醇

炔雌醇（全稱乙炔雌二醇，英語：Ethinylestradiol，縮寫EE），3-羥基-19-去甲-17α-孕甾-1,3,5(10)-三烯-20-炔-17-醇，17α-Ethynylestra-1,3,5(10)-triene-3,17β-diol，分子式C₂₀H₂₄O₂^[1]，是一種雌激素藥物^[8]，廣泛作為避孕藥使用^[7][10][11]。

炔雌醇

臨床資料
讀音	/ˌɛθɪnɪlˌɛstrəˈdaɪ.əl/
商品名（英語：Drug nomenclature）	Numerous
其他名稱	Ethynylestradiol; Ethinyl estradiol; Ethinyl oestradiol; EE; EE2; 17α-Ethynylestradiol; 17α-Ethynylestra-1,3,5(10)-triene-3,17β-diol; NSC-10973[1]
AHFS/Drugs.com	國際藥品名稱
MedlinePlus	a604032
核准狀況	歐 EMA: yes
懷孕分級	X (USA)
給藥途徑	• By mouth (tablet) • Transdermal (patch) • Vaginal (ring)
藥物類別	Estrogen
ATC碼	G03CA01 (WHO) L02AA03
法律規範狀態
法律規範	處方藥（℞-only）
藥物動力學數據
生物利用度	38–48%[2][3][4]
血漿蛋白結合率	97–98% (to albumin;[5] is not bound to SHBG)[6]
藥物代謝	Liver (primarily CYP3A4)[9]
代謝產物	• Ethinylestradiol sulfate[7][8] • Others[7][8]
生物半衰期	7–36 hours[9][2][10][11]
排泄途徑	Feces: 62%[10] Urine: 38%[10]
識別資訊
IUPAC命名法 (8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
CAS號	57-63-6  Y
PubChem CID	5991
IUPHAR/BPS	7071
DrugBank	DB00977 Y
ChemSpider	5770 Y
UNII	423D2T571U
KEGG	D00554 Y
ChEBI	CHEBI:4903 Y
ChEMBL	ChEMBL691 Y
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID5020576
ECHA InfoCard	100.000.311
化學資訊
化學式	C20H24O2
摩爾質量	296.41 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像
熔點	182至184 °C（360至363 °F）
SMILES Oc1cc4c(cc1)[C@H]3CC[C@]2([C@@H](CC[C@]2(C#C)O)[C@@H]3CC4)C
InChI InChI=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 Y Key:BFPYWIDHMRZLRN-SLHNCBLASA-N Y

另見

• 醋酸烯諾孕酮/乙炔雌二醇
• 炔雌醇/左炔諾孕酮
• 炔雌醇/依託孕烯

參考文獻

1. J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014: 522–. ISBN 978-1-4757-2085-3.
2. Goldzieher JW, Brody SA. Pharmacokinetics of ethinyl estradiol and mestranol. American Journal of Obstetrics and Gynecology. 1990, 163 (6 Pt 2): 2114–9. PMID 2256522. doi:10.1016/0002-9378(90)90550-Q.
3. Fruzzetti F, Trémollieres F, Bitzer J. An overview of the development of combined oral contraceptives containing estradiol: focus on estradiol valerate/dienogest. Gynecological Endocrinology. 2012, 28 (5): 400–8. PMC 3399636 . PMID 22468839. doi:10.3109/09513590.2012.662547.
4. Fotherby K. Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy. Contraception. August 1996, 54 (2): 59–69. PMID 8842581. doi:10.1016/0010-7824(96)00136-9.
5. Facts and Comparisons (Firm); Ovid Technologies, Inc. Drug Facts and Comparisons 2005: Pocket Version. Facts and Comparisons. 2005: 121. ISBN 978-1-57439-179-4.
6. Micromedex. USP DI 2003: Drug Information for Healthcare Professionals. Thomson Micromedex. 1 January 2003: 1253, 1258, 1266 [2022-11-27]. ISBN 978-1-56363-429-1. （原始內容存檔於2023-01-10）.
7. Kuhl H. Pharmacology of estrogens and progestogens: influence of different routes of administration (PDF). Climacteric. 2005,. 8 Suppl 1: 3–63 [2022-11-27]. PMID 16112947. S2CID 24616324. doi:10.1080/13697130500148875. （原始內容存檔 (PDF)於2019-03-27）.
8. Michael Oettel; Ekkehard Schillinger. Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. 6 December 2012: 390. ISBN 978-3-642-60107-1.
9. Claude L Hughes; Michael D. Waters. Translational Toxicology: Defining a New Therapeutic Discipline. Humana Press. 23 March 2016: 73–. ISBN 978-3-319-27449-2.
10. Stanczyk FZ, Archer DF, Bhavnani BR. Ethinyl estradiol and 17β-estradiol in combined oral contraceptives: pharmacokinetics, pharmacodynamics and risk assessment. Contraception. 2013, 87 (6): 706–27. PMID 23375353. doi:10.1016/j.contraception.2012.12.011.
11. Shellenberger, T. E. Pharmacology of estrogens. The Climacteric in Perspective. 1986: 393–410. ISBN 978-94-010-8339-3. doi:10.1007/978-94-009-4145-8_36. 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.

外部連結