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]

Other namesEE3; 17α-Ethynylestriol; 17α-Ethynylestra-1,3,5(10)-triene-3,16α,17β-triol

Routes of
administrationBy mouth

Drug classEstrogen

CAS Number

• 4717-40-2 ^Y

Quick facts Clinical data, Other names ...

Ethinylestriol

Clinical data
Other names	EE3; 17α-Ethynylestriol; 17α-Ethynylestra-1,3,5(10)-triene-3,16α,17β-triol
Routes of administration	By mouth
Drug class	Estrogen
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	4717-40-2 Y
PubChem CID	11723045
ChemSpider	9897761
UNII	PVH6K749AL
ChEMBL	ChEMBL1627607
Chemical and physical data
Formula	C20H24O3
Molar mass	312.409 g·mol−1
3D model (JSmol)	Interactive image
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

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