Ethinylestradiol sulfate

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.[1][2][3] 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][3][1] 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).[1] 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.[5] However, other studies have suggested that EE sulfate may nonetheless contribute up to 20% of total EE levels.[2][6]

Not to be confused with Ethinylestradiol sulfonate or Ethinylestradiol sulfamate.
Ethinylestradiol sulfate
Clinical data
Other namesEE sulfate; 17α-Ethynylestradiol 3-sulfate
Drug classEstrogen; Estrogen ester
Identifiers
IUPAC name
  • [(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] hydrogen sulfate
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H24O5S
Molar mass376.47 g·mol−1
3D model (JSmol)
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
InChI
  • InChI=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
  • Key:WLGIWVFFGMPRLM-SLHNCBLASA-N

See also

References
  1. Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  2. Michael Oettel; Ekkehard Schillinger (6 December 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp. 284–285, 290. ISBN 978-3-642-60107-1.
  3. Fotherby K (August 1996). "Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy". Contraception. 54 (2): 59–69. doi:10.1016/0010-7824(96)00136-9. PMID 8842581.
  4. Goldzieher JW, Mileikowsky G, Newburger J, Dorantes A, Stavchansky SA (1988). "Human pharmacokinetics of ethynyl estradiol 3-sulfate and 17-sulfate". Steroids. 51 (1–2): 63–79. doi:10.1016/0039-128x(88)90185-7. PMID 3242167. S2CID 21188869.
  5. Donna Shoupe; Florence P. Haseltine (6 December 2012). Contraception. Springer Science & Business Media. pp. 19–. ISBN 978-1-4612-2730-4.
  6. Mattison DR, Karyakina N, Goodman M, LaKind JS (September 2014). "Pharmaco- and toxicokinetics of selected exogenous and endogenous estrogens: a review of the data and identification of knowledge gaps". Crit. Rev. Toxicol. 44 (8): 696–724. doi:10.3109/10408444.2014.930813. PMID 25099693. S2CID 11212469.



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