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Ethinylestradiol sulfonate

Not to be confused with Ethinylestradiol sulfate or Ethinylestradiol sulfamate.
Ethinylestradiol sulfonate
Clinical data
Trade namesDeposiston, Turisteron[1]
Other namesEES; Turisteron; J96; Ethinylestradiol 3-isopropylsulfonate; Ethinylestradiol 3-(2-propanesulfonate); 17α-Ethynyl-3-isopropyl-sulfonyloxyestradiol
Routes of
administration		By mouth[2][3]
Drug classEstrogen; Estrogen ester
Pharmacokinetic data
Metabolites• Ethinylestradiol[2][3]
Elimination half-lifeOral: 6 days[4]
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)
  • 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

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.[1][5][2][3][6] It has also been investigated in the treatment of breast cancer in women.[4][7] The medication was combined with norethisterone acetate in birth control pills.[1] EES is taken by mouth once per week.[1][5][2][3]

Side effects of EES in men include breast tenderness, gynecomastia, feminization, sexual dysfunction, and cardiovascular complications, among others.[5][2] EES is a synthetic estrogen and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol.[2][3] It is an estrogen ester and a long-lasting prodrug of ethinylestradiol in the body.[2][3] 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.[2][4]

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.[1][3] It has been marketed in Germany, but may no longer be available.[8][9][10]

  1. ^ a b c d e Schwarz S, Onken D, Schubert A (July 1999). "The steroid story of Jenapharm: from the late 1940s to the early 1970s". Steroids. 64 (7): 439–445. doi:10.1016/S0039-128X(99)00003-3. PMID 10443899. S2CID 40156824. 6.2. New estrogens. In 1967, Jenapharm, in conjunction with the Academy of Sciences (Kurt Ponsold, Gu¨nter Bruns, and Kurt Schubert in Jena and Hans Schick and Bernard Lu¨cke in Berlin), started a program of searching for new estrogens. [...] orally administered, strongly active estrogens with a depot effect. [...] the second objective was successfully attained. The rationale that an a-branched alkanesulfonic acid ester of ethinyl estradiol with a medium chain length should lead to a depot effect without the danger of active ingredient accumulation on longer usage [15] led in 1978 to the first once-a-week oral contraceptive (DEPOSISTONt), a combination of ethinylestradiol 3-isopropylsulfonate (17) and norethisterone acetate [16]. TURISTERONt, an estrogenic monotherapy with compound 17 that can still justify its position today [17], followed in 1980, as a therapy of prostate cancer. [...]
  2. ^ a b c d e f g h Oestell M (6 December 2012). "Estrogens and Antiestrogen in the Male". In Oettel M, Schillinger E (eds.). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Handbook of Experimental Pharmacology. Vol. 135 / 2. Springer Science & Business Media. pp. 248, 277, 369, 540, 542. doi:10.1007/978-3-642-60107-1. ISBN 978-3-642-60107-1. S2CID 35733673.
  3. ^ a b c d e f g Elger W, Palme HJ, Schwarz S (April 1998). "Novel oestrogen sulfamates: a new approach to oral hormone therapy". Expert Opinion on Investigational Drugs. 7 (4): 575–589. doi:10.1517/13543784.7.4.575. PMID 15991994.
  4. ^ a b c Cite error: The named reference pmid7103689 was invoked but never defined (see the help page).
  5. ^ a b c Höfling G, Heynemann H (1998). "Die orale Östrogentherapie des fortgeschrittenen Prostatakarzinoms — Anlaß für eine Neubewertung?" [Oral Estrogen Therapy for Advanced Prostate Cancer — Reason for Revaluation?]. Der Urologe B. 38 (2): 165–170. doi:10.1007/s001310050185. ISSN 0042-1111.
  6. ^ Dörner G, Schnorr D, Stahl F, Rohde W (December 1985). "Successful treatment of prostatic cancer with the orally active depot estrogen ethinylestradiol sulfonate (Turisteron)". Experimental and Clinical Endocrinology. 86 (2): 190–196. doi:10.1055/s-0029-1210486. PMID 3912197.
  7. ^ Cite error: The named reference MonfardiniBrunner2012 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Martindale was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
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