LIPID MAPS

Ethynyl estradiol is an estrogen receptor agonist (EC50 = 8.5 pM in a reporter assay using T47D cells).¹ It reduces serum cholesterol levels and femur bone mass and increases uterine mass in an ovariectomized (OVX) rat model of postmenopause when administered at a dose of 0.1 mg/kg per day.² Ethynyl estradiol also has been found in wastewater effluent, and it prevents secondary sexual development in male fathead minnows (P. promelas) and increases the numbers of intersex fish when used at a concentration of 4 ng/l.^3,4 Formulations containing ethynyl estradiol have been used as contraceptives.

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References

1. Wilson, V.S., Bobseine, K., and Gray, L.E., Jr. Development and characterization of a cell line that stably expresses an estrogen-responsive luciferase reporter for the detection of estrogen receptor agonist and antagonists. Toxicol. Sci. 81(1), 69-77 (2004).

2. Bryant, H.U., and Dere, W.H. Selective estrogen receptor modulators: An alternative to hormone replacement therapy. Proc. Soc. Exp. Biol. Med. 217(1), 45-52 (1998).

3. Länge, R., Hutchinson, T.H., Croudace, C.P., et al. Effects of the synthetic estrogen 17α-ethinylestradiol on the life-cycle of the fathead minnow (Pimephales promelas). Environ. Toxicol. Chem. 20(6), 1216-1227 (2001).

4. Desbrow, C., Routledge, E.J., Brighty, G.C., et al. Identification of estrogenic chemicals in STW effluent. 1. Chemical fractionation and in vitro biological screening. Environ. Sci. Technol. 32(11), 1549-1558 (1998).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Neue per os-wirksame weibliche Keimdrüsenhormon-Derivate: 17-Aethinyl-oestradiol und Pregnen-in-on-3-ol-17,
Naturwissenschaften, 1938

DOI: 10.1007/BF01681040

String Representations

InChiKey (Click to copy)

BFPYWIDHMRZLRN-SLHNCBLASA-N

InChi (Click to copy)

InChI=1S/C20H24O2/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/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1

SMILES (Click to copy)

[C@@]12([H])CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3C=CC(O)=CC=3CC[C@@]21[H]