Ethinylestradiol sulfate explained

Iupac Name:[(8''R'',9''S'',13''S'',14''S'',17''R'')-17-Ethynyl-17-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6''H''-cyclopenta[''a'']phenanthren-3-yl] hydrogen sulfate
Width:250px
Class:Estrogen
Estrogen ester
Cas Number:24560-70-1
Pubchem:68575
Chemspiderid:61845
Unii:67P0FM71OZ
Chebi:136600
Chembl:1614648
Synonyms:EE sulfate; 17α-Ethynylestradiol 3-sulfate
C:20
H:24
O:5
S:1
Smiles:C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OS(=O)(=O)O
Stdinchi:1S/C20H24O5S/c1-3-20(21)11-9-18-17-6-4-13-12-14(25-26(22,23)24)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21H,4,6,8-11H2,2H3,(H,22,23,24)/t16-,17-,18+,19+,20+/m1/s1
Stdinchikey:WLGIWVFFGMPRLM-SLHNCBLASA-N

Ethinylestradiol sulfate (EE sulfate), also known as 17α-ethynylestradiol 3-sulfate, is an estrogen ester – specifically, the C3 sulfuric acid (sulfate) ester of the synthetic estrogen ethinylestradiol (EE) – and is the major metabolite of EE.[1] [2] [3] Circulating levels of EE sulfate range from 6 to 22 times those of EE when EE is taken orally. EE sulfate can be transformed back into EE (14–21%) via steroid sulfatase, and it has been suggested that EE sulfate may serve as a circulating reservoir for EE, similarly to the case of estrone sulfate with estradiol.[4] [5] However, the EE sulfate pool with EE is far smaller than the pool of estrone sulfate that occurs with estradiol (with estrone sulfate levels approximately 200-fold higher than estradiol levels on average with oral estradiol). In addition, in contrast to the case of estrone sulfate and estrone, the conversion rate of EE sulfate back into EE is relatively low, and has been said probably isn't of clinical significance. However, other studies have suggested that EE sulfate may nonetheless contribute up to 20% of total EE levels.[6]

See also

Notes and References

  1. Kuhl H . Pharmacology of estrogens and progestogens: influence of different routes of administration . Climacteric . 8 . Suppl 1 . 3–63 . August 2005 . 16112947 . 10.1080/13697130500148875 . 24616324 .
  2. Book: Kuhnz W, Blade H, Zimmermann H . Pharmacokinetics and Exogenous Natural and Synthetic Estrogens and Antiestrogens . Oettel M, Schillinger E . Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA284 . 6 December 2012. Springer Science & Business Media. 978-3-642-60107-1. 284–285, 290.
  3. Fotherby K . Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy . Contraception . 54 . 2 . 59–69 . August 1996 . 8842581 . 10.1016/0010-7824(96)00136-9 .
  4. Goldzieher JW, Mileikowsky G, Newburger J, Dorantes A, Stavchansky SA . Human pharmacokinetics of ethynyl estradiol 3-sulfate and 17-sulfate . Steroids . 51 . 1–2 . 63–79 . 1988 . 3242167 . 10.1016/0039-128x(88)90185-7 . 21188869 .
  5. Book: Goldzieher JW . Pharmacology of Contraceptive Steroids. Shoupe D, Haseltine FP . Contraception. https://books.google.com/books?id=cpDhBwAAQBAJ&pg=PA19. 6 December 2012. Springer Science & Business Media. 978-1-4612-2730-4. 19–.
  6. Mattison DR, Karyakina N, Goodman M, LaKind JS . Pharmaco- and toxicokinetics of selected exogenous and endogenous estrogens: a review of the data and identification of knowledge gaps . Critical Reviews in Toxicology . 44 . 8 . 696–724 . September 2014 . 25099693 . 10.3109/10408444.2014.930813 . 11212469 .