19-去甲孕酮

化合物

19-去甲孕酮(英语:19-Norprogesterone)也叫做19-去甲孕甾-4-烯-3,20-二酮(英语:19-norpregn-4-ene-3,20-dione)是性激素孕酮的结构类似物,只少了19号C原子的甲基。19-去甲孕酮首次合成于1944年,但1944年的产物带有多种立体异构[1][2][3][4]

19-去甲孕酮
临床资料
其他名称10-Norprogesterone; 19-Norpregn-4-ene-3,20-dione; 17β-Acetylestr-4-en-3-one
给药途径不经肠
药物类别英语Drug classProgestin; Progestogen; Mineralocorticoid
识别信息
  • (8R,9S,10R,13S,14S,17S)-17-acetyl-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
CAS号472-54-8
PubChem CID
ChemSpider
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
化学信息
化学式C20H28O2
摩尔质量300.435 g/mol
3D模型(JSmol英语JSmol
熔点144至145 °C(291至293 °F)
  • O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@@H](C(=O)C)CC[C@H]3[C@@H]1CC2)C)CC4
  • InChI=1S/C20H28O2/c1-12(21)18-7-8-19-17-5-3-13-11-14(22)4-6-15(13)16(17)9-10-20(18,19)2/h11,15-19H,3-10H2,1-2H3/t15-,16+,17+,18+,19-,20+/m0/s1
  • Key:NVUUMOOKVFONOM-GPBSYSOESA-N

参考文献

  1. ^ Ehrenstein, Maximilian. INVESTIGATIONS ON STEROIDS. VIII. LOWER HOMOLOGS OF HORMONES OF THE PREGNANE SERIES: 10-NOR-11-DESOXY-CORTICOSTERONE ACETATE AND 10-NORPROGESTERONE1. The Journal of Organic Chemistry. 1944, 09 (5): 435–456. ISSN 0022-3263. doi:10.1021/jo01187a009. 
  2. ^ Allen WM, Ehrenstein M. 10-NOR-PROGESTERONE, A PHYSIOLOGICALLY ACTIVE LOWER HOMOLOG OF PROGESTERONE. Science. 1944, 100 (2594): 251–2. PMID 17738394. doi:10.1126/science.100.2594.251. 
  3. ^ Miramontes, L.; Rosenkranz, G.; Djerassi, Carl. STEROIDS. XXII. THE SYNTHESIS OF 19-NORPROGESTERONE. Journal of the American Chemical Society. 1951, 73 (7): 3540–3541. ISSN 0002-7863. doi:10.1021/ja01151a547. 
  4. ^ Djerassi, Carl; Miramontes, L.; Rosenkranz, G. Steroids. XLVIII.119-Norprogesterone, a Potent Progestational Hormone. Journal of the American Chemical Society. 1953, 75 (18): 4440–4442. ISSN 0002-7863. doi:10.1021/ja01114a013.