Ethinylestradiol sulfonate

Ethinylestradiol sulfonate (EES), sold under the brand names Deposiston and Turisteron among others, is an estrogen medication which has been used in birth control pills for women and in the treatment of prostate cancer in men. It has also been investigated in the treatment of breast cancer in women. The medication was combined with norethisterone acetate in birth control pills. EES is taken by mouth once per week.

Not to be confused with Ethinylestradiol sulfate or Ethinylestradiol sulfamate.
Ethinylestradiol sulfonate
Clinical data
Trade namesDeposiston, Turisteron
Other namesEES; Turisteron; J96; Ethinylestradiol 3-isopropylsulfonate; Ethinylestradiol 3-(2-propanesulfonate); 17α-Ethynyl-3-isopropyl-sulfonyloxyestradiol
Routes of
administration		By mouth
Drug classEstrogen; Estrogen ester
Pharmacokinetic data
Metabolites• Ethinylestradiol
Elimination half-lifeOral: 6 days
Identifiers
  • [(8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] propane-2-sulfonate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H30O4S
Molar mass402.55 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)S(=O)(=O)OC1=CC2=C(C=C1)C3CCC4(C(C3CC2)CCC4(C#C)O)C
  • InChI=1S/C23H30O4S/c1-5-23(24)13-11-21-20-8-6-16-14-17(27-28(25,26)15(2)3)7-9-18(16)19(20)10-12-22(21,23)4/h1,7,9,14-15,19-21,24H,6,8,10-13H2,2-4H3/t19-,20-,21+,22+,23+/m1/s1
  • Key:KPEUDULLQDHKAZ-VROINQGHSA-N

Side effects of EES in men include breast tenderness, gynecomastia, feminization, sexual dysfunction, and cardiovascular complications, among others. EES is a synthetic estrogen and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol. It is an estrogen ester and a long-lasting prodrug of ethinylestradiol in the body. EES is rapidly taken up into fat and slowly released from it, resulting in a biological half-life of about 6 days with the oral route and allowing the medication to be taken only once per week.

EES was first synthesized in 1967, was first introduced as a birth control pill in 1978, and was introduced for the treatment of prostate cancer in 1980. It has been marketed in Germany, but may no longer be available.

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