Chemistry:Ethinylestradiol sulfate
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| Other names | EE sulfate; 17α-Ethynylestradiol 3-sulfate |
| Drug class | Estrogen; Estrogen ester |
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| Formula | C20H24O5S |
| Molar mass | 376.47 g·mol−1 |
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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]
See also
References
- ↑ 1.0 1.1 1.2 1.3 "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric 8 (Suppl 1): 3–63. August 2005. doi:10.1080/13697130500148875. PMID 16112947.
- ↑ 2.0 2.1 2.2 "Pharmacokinetics and Exogenous Natural and Synthetic Estrogens and Antiestrogens". Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. 6 December 2012. pp. 284–285,290. ISBN 978-3-642-60107-1. https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA284.
- ↑ 3.0 3.1 3.2 "Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy". Contraception 54 (2): 59–69. August 1996. doi:10.1016/0010-7824(96)00136-9. PMID 8842581.
- ↑ "Human pharmacokinetics of ethynyl estradiol 3-sulfate and 17-sulfate". Steroids 51 (1–2): 63–79. 1988. doi:10.1016/0039-128x(88)90185-7. PMID 3242167.
- ↑ 5.0 5.1 "Pharmacology of Contraceptive Steroids". Contraception. Springer Science & Business Media. 6 December 2012. pp. 19–. ISBN 978-1-4612-2730-4. https://books.google.com/books?id=cpDhBwAAQBAJ&pg=PA19.
- ↑ "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. doi:10.3109/10408444.2014.930813. PMID 25099693.
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