Ethinylestriol

Ethinylestriol (EE3), or 17α-ethynylestriol, also known as 17α-ethynylestra-1,3,5(10)-triene-3,16α,17β-triol, is a synthetic estrogen which was never marketed.[1] Nilestriol, the 3-cyclopentyl ether of ethinylestriol, is a prodrug of ethinylestriol, and is a more potent estrogen in comparison,[1] but, in contrast to ethinylestriol, has been marketed.[2] Ethinylestriol has been found to reduce the risk of 7,12-dimethylbenz(a)anthracene (DMBA)-induced mammary cancer when given as a prophylactic in animal models, while other estrogens like ethinylestradiol and diethylstilbestrol were ineffective.[3]

Not to be confused with Ethinylestradiol.
Ethinylestriol
Clinical data
Other namesEE3; 17α-Ethynylestriol; 17α-Ethynylestra-1,3,5(10)-triene-3,16α,17β-triol
Routes of
administration		By mouth
Drug classEstrogen
Identifiers
IUPAC name
  • (8R,9S,13S,14S,16R,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,16,17-triol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC20H24O3
Molar mass312.409 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@]2(C#C)O)O)CCC4=C3C=CC(=C4)O
InChI
  • InChI=1S/C20H24O3/c1-3-20(23)18(22)11-17-16-6-4-12-10-13(21)5-7-14(12)15(16)8-9-19(17,20)2/h1,5,7,10,15-18,21-23H,4,6,8-9,11H2,2H3/t15-,16-,17+,18-,19+,20+/m1/s1
  • Key:VSODIPLKPBLGCC-NADOGSGZSA-N

See also

References
  1. McGuire W (14 December 2013). Experimental Biology. Springer Science & Business Media. pp. 161–. ISBN 978-1-4757-4673-0.
  2. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 891–. ISBN 978-1-4757-2085-3.
  3. Lemon HM (December 1987). "Antimammary carcinogenic activity of 17-alpha-ethinyl estriol". Cancer. 60 (12): 2873–81. doi:10.1002/1097-0142(19871215)60:12<2873::AID-CNCR2820601204>3.0.CO;2-B. PMID 3119187.
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