异炔诺酮

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 nomenclature）	Enovid (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 class）	Progestin; Progestogen; Estrogen
ATC码	G03FA09 (WHO)
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
IUPAC命名法 (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  Y
PubChem CID	6231
DrugBank	DB09371 Y
ChemSpider	5995 Y
UNII	88181ACA0M
KEGG	D05207
ChEBI	CHEBI:34895 Y
ChEMBL	ChEMBL1387 Y
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID3021069
ECHA InfoCard	100.000.620
化学信息
化学式	C20H26O2
摩尔质量	298.419 g/mol
3D模型（JSmol（英语：JSmol））	交互式图像
SMILES O=C4CCC\1=C(\CC[C@@H]2[C@@H]/1CC[C@]3([C@H]2CC[C@]3(C#C)O)C)C4
InChI 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 Y Key:ICTXHFFSOAJUMG-SLHNCBLASA-N Y

参考文献

1. 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. 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. 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. 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.