Ethinylestradiol sulfonate

Source: Wikipedia, the free encyclopedia.
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
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

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]

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]

Medical uses

EES has been used in combination with

high-dose estrogen therapy in the treatment of prostate cancer.[1][5][3][6][11] It has also been assessed in the treatment of breast cancer.[4][7] The medication is used at a dosage of 1 mg once per week in birth control pills and 1 to 2 mg once per week in the treatment of prostate cancer.[12][5][2] The 1 week and 2 mg/week dosages of EES are equivalent to daily doses of 0.143 mg and 0.285 mg EES, respectively.[13]

EES has been used in combination with

medical castration in the treatment of prostate cancer.[13]

Available forms

See also: Ethinylestradiol sulfonate/norethisterone acetate

EES was available alone for the treatment of prostate cancer in men in the form of 1 mg oral tablets[14][15] and in combination with norethisterone acetate in the form of oral tablets containing 1 mg EES and 5 mg norethisterone acetate for use as a birth control pill for women.[15][16][1]

Side effects

heart attack (2.3 to 18%), stroke (2.3 to 3.0%), and coronary artery disease (3.3%).[5][2]

EES has been described as having good

metabolic effects and VTE risk as combined birth control pills containing EE.[17][18][19]

Pharmacology

Ethinylestradiol (EE), the active form of EES.

EES is an

elimination half-life of about 6 days.[4] This allows it to be taken once per week.[3][2] Both EES and the related medication quinestrol have been described as depot oral estrogens.[1][12][2]

EES is a powerful antigonadotropin, and is capable of suppressing circulating total testosterone levels in men to concentrations comparable to those seen with castration (less than 1 to 3% of initial values).[6][21][11] In addition, EES can strongly increase sex hormone-binding globulin (SHBG) levels, thereby additionally decreasing free testosterone levels.[5][22][23][21] As such, EES is a powerful functional antiandrogen, which makes it useful for treating prostate cancer.[24][21]

The biological half-life of EES in blood has been reported to be 3 hours.[14]

Chemistry

See also: Estrogen ester, List of estrogens § Estradiol derivatives, and List of estrogen esters § Esters of other steroidal estrogens

EES, also known as ethinylestradiol 3-isopropylsulfonate or ethinylestradiol 3-(2-propanesulfonate), is a

derivative of estradiol. Specifically, it is the C3 isopropylsulfonate ester of ethinylestradiol (17α-ethynylestradiol).[20][8][2] EES is similar to quinestrol (EE 3-cyclopentyl ether), which is a C3 ether of EE and is a long-lasting oral depot estrogen similarly.[2]

estradiol 17β-(1-(4-(aminosulfonyl)benzoyl)-L-proline) (EC508), which are highly potent oral estradiol prodrugs that bind to erythrocytes similarly and are under investigation for potential clinical use.[1][2][3][25][26]

History

EES was first synthesized in 1967 at Jenapharm.[1][3] It was first introduced for use in combination with norethisterone acetate under the brand name Deposiston as a once-a-week birth control pill for women in 1978.[1] The medication was subsequently introduced by itself under the brand name Turisteron for the treatment of prostate cancer in men in 1980.[1]

Society and culture

Generic names

Ethinylestradiol sulfonate is the

INNTooltip International Nonproprietary Name or other such designations.[20][8] EES has also been known by its former developmental code name J96.[3]

Brand names

EES has been marketed in combination with norethisterone acetate under the brand name Deposiston for use as a birth control pill in women and under the brand name Turisteron for use in prostate cancer in men.[1][20][8]

Availability

EES has been marketed in Germany, though it appears that it may no longer be available.[8][9][10]

See also

References

  1. ^
    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. ^
    S2CID 35733673
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  3. ^
    PMID 15991994
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  4. ^
    PMID 7103689
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  5. ^
    ISSN 0042-1111
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  6. ^
    PMID 3912197
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  7. ^
    S2CID 35835002
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  8. ^
    ISBN 978-3-88763-075-1
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  9. ^
    ISBN 978-0-85369-840-1
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  10. ^ a b [1][dead link]
  11. ^
    S2CID 40497389
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  12. ^
    PMID 2184606
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  13. ^
    ISBN 978-3-642-60064-7
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  14. ^
    ISBN 978-3-662-07635-4
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  15. ^
    ISBN 978-3-662-08108-2
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  16. ISBN 978-3-7692-2114-5
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  17. PMID 27793376
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  18. PMID 23384743
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  19. S2CID 23760705
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  20. ^
    ISBN 978-1-4757-2085-3
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  21. ^
    PMID 3126615
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  22. ISBN 978-92-832-1291-1
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  23. ISBN 978-3-319-53298-1
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  24. PMID 3111122
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  25. PMID 11800168
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  26. S2CID 26650319
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Further reading
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