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]。
 | |
 | |
| 臨床資料 | |
|---|---|
| 讀音 | /ˌɛθɪnɪlˌɛstrəˈdaɪ.əl/ |
| 商品名 | 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 | |
| 懷孕分級 |
|
| 給藥途徑 | • By mouth (tablet) • Transdermal (patch) • Vaginal (ring) |
| 藥物類別 | Estrogen |
| ATC碼 | |
| 法律規範狀態 | |
| 法律規範 |
|
| 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 | |
| |
| CAS號 | 57-63-6  |
| PubChem CID | |
| IUPHAR/BPS | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| 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） | |
| 熔點 | 182至184 °C（360至363 °F） |
| |
| |
另見
編輯參考文獻
編輯- ^ 1.0 1.1 J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014: 522–. ISBN 978-1-4757-2085-3.
- ^ 2.0 2.1 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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）.
- ^ 7.0 7.1 7.2 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）.
- ^ 8.0 8.1 8.2 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.
- ^ 9.0 9.1 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.
- ^ 10.0 10.1 10.2 10.3 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.
- ^ 11.0 11.1 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.
