异炔诺酮

化合物

异炔诺酮(英语:Noretynodrel 或 英语:norethynodrel商品名:Enovid等)是一种黄体制剂药物,过去被用于口服避孕药以及治疗一些妇科疾病,但现在已不再使用[3][6][7][8]。异炔诺酮和炔诺酮的不同之处在于双键位于5(10)号位而非4(5)号位。

异炔诺酮
临床资料
商品名英语Drug nomenclatureEnovid (with mestranol), others
其他名称Norethynodrel; Noretinodrel Norethinodrel; NYD; SC-4642; NSC-15432; 5(10)-Norethisterone; 17α-Ethinyl-19-nor-5(10)-testosterone; 17α-Ethynyl-δ5(10)-19-nortestosterone; 17α-Ethynylestr-5(10)-en-17β-ol-3-one; 19-Nor-17α-pregn-5(10)-en-20-yn-17β-ol-3-one
给药途径口服给药
药物类别英语Drug classProgestin; Progestogen; Estrogen
ATC码
药物动力学数据
血浆蛋白结合率Noretynodrel: to albumin and not to SHBG or CBG[1]
药物代谢Liver, intestines (hydroxylation, isomerization, conjugation)[1][3]
代谢产物• 3α-Hydroxynoretynodrel[2]
• 3β-Hydroxynoretynodrel[2]
Norethisterone[2][1][3]
Ethinylestradiol[3][4]Conjugates[3]
生物半衰期Very short (< 30 minutes)[5]
排泄途径Breast milk: 1%[6]
识别信息
  • (8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS号68-23-5  checkY
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.000.620 编辑维基数据链接
化学信息
化学式C20H26O2
摩尔质量298.419 g/mol
3D模型(JSmol英语JSmol
  • O=C4CCC\1=C(\CC[C@@H]2[C@@H]/1CC[C@]3([C@H]2CC[C@]3(C#C)O)C)C4
  • InChI=1S/C20H26O2/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/h1,16-18,22H,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1 checkY
  • Key:ICTXHFFSOAJUMG-SLHNCBLASA-N checkY

参考文献

  1. ^ 1.0 1.1 1.2 Kuhl H. Pharmacokinetics of oestrogens and progestogens. Maturitas. September 1990, 12 (3): 171–97. PMID 2170822. doi:10.1016/0378-5122(90)90003-O. 
  2. ^ 2.0 2.1 2.2 Jin Y, Duan L, Chen M, Penning TM, Kloosterboer HJ. Metabolism of the synthetic progestogen norethynodrel by human ketosteroid reductases of the aldo-keto reductase superfamily. J. Steroid Biochem. Mol. Biol. 2012, 129 (3–5): 139–44. PMC 3303946 . PMID 22210085. doi:10.1016/j.jsbmb.2011.12.002. 
  3. ^ 3.0 3.1 3.2 3.3 3.4 Kuhl H. Pharmacology of estrogens and progestogens: influence of different routes of administration (PDF). Climacteric. 2005,. 8 Suppl 1: 3–63 [2019-06-30]. PMID 16112947. doi:10.1080/13697130500148875. (原始内容存档 (PDF)于2016-08-22). 
  4. ^ Kuhl H. Pharmacology of Progestogens (PDF). J Reproduktionsmed Endokrinol. 2011, 8 (1): 157–177 [2019-07-10]. (原始内容存档 (PDF)于2016-10-11). 
  5. ^ Hammerstein J. Prodrugs: advantage or disadvantage?. Am. J. Obstet. Gynecol. 1990, 163 (6 Pt 2): 2198–203. PMID 2256526. 
  6. ^ 6.0 6.1 Sweetman, Sean C. (编). Sex hormones and their modulators. Martindale: The Complete Drug Reference 36th. London: Pharmaceutical Press. 2009: 2120–2121. ISBN 978-0-85369-840-1. 
  7. ^ Jucker. Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Birkhäuser. 21 December 2013: 85–88 [2019-06-30]. ISBN 978-3-0348-7065-8. (原始内容存档于2021-03-14). 
  8. ^ Lara Marks. Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. 2010: 74–75. ISBN 978-0-300-16791-7.