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 names	17α-Ethylestradiol; 17α-Ethylestra-1,3,5(10)-triene-3,17β-diol
Drug class	Estrogen
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	2553-34-6
PubChem CID	66428
ChEMBL	ChEMBL1627625
CompTox Dashboard (EPA)	DTXSID10948429
Chemical and physical data
Formula	C20H28O2
Molar mass	300.442 g·mol^−1
3D model (JSmol)	Interactive image
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

• List of estrogens
• 5α-Dihydronorethandrolone

References

1. William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 330–, 591–598. ISBN 978-0-9828280-1-4.
2. Colton, Frank B.; Nysted, Leonard N.; Riegel, Byron; Raymond, Albert L (1957). "17-Alkyl-19-nortestosterones". Journal of the American Chemical Society. 79 (5): 1123–1127. doi:10.1021/ja01562a028. ISSN 0002-7863.
3. Fedorova, O. I.; Pekarskaya, E. S.; Lukashina, I. V.; Grinenko, G. S. (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.
4. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1513–. ISBN 978-0-8155-1856-3.