Ethylestradiol

Ethylestradiol, or 17α-ethylestradiol, also known as 17α-ethylestra-1,3,5(10)-triene-3,17β-diol, is a synthetic estrogen which was never marketed. It occurs as an active metabolite of the anabolic steroids norethandrolone and ethylestrenol formed via aromatase and is believed to be responsible for the estrogenic effects of norethandrolone and ethylestrenol.[1] The 3-methyl ether of ethylestradiol has been used as an intermediate in the synthesis of certain 19-nortestosterone anabolic steroids.[2][3][4]

Not to be confused with Ethinylestradiol or Ethylestrenol.
Ethylestradiol
Clinical data
Other names17α-Ethylestradiol; 17α-Ethylestra-1,3,5(10)-triene-3,17β-diol
Drug classEstrogen
Identifiers
IUPAC name
  • (8R,9S,13S,14S,17S)-17-Ethyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChem CID
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H28O2
Molar mass300.442 g·mol−1
3D model (JSmol)
SMILES
  • CC[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)O)C)O
InChI
  • InChI=1S/C20H28O2/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/h5,7,12,16-18,21-22H,3-4,6,8-11H2,1-2H3/t16-,17-,18+,19+,20+/m1/s1
  • Key:GQHYKMYMSVJXJM-SLHNCBLASA-N

See also

References
  1. Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 330–, 591–598. ISBN 978-0-9828280-1-4.
  2. Colton FB, Nysted LN, Riegel B, Raymond AL (1957). "17-Alkyl-19-nortestosterones". Journal of the American Chemical Society. 79 (5): 1123–1127. doi:10.1021/ja01562a028. ISSN 0002-7863.
  3. Fedorova OI, Pekarskaya ES, Lukashina IV, Grinenko GS (1974). "Synthesis of some derivatives op 19-nortestosterone from estra-1,3,5(10)-trienes". Pharmaceutical Chemistry Journal. 8 (8): 462–465. doi:10.1007/BF00757882. ISSN 0091-150X. S2CID 27243268.
  4. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1513–. ISBN 978-0-8155-1856-3.
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