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词条 Ethinylestradiol sulfate
释义

  1. See also

  2. References

{{Distinguish|Ethinylestradiol sulfonate|Ethinylestradiol sulfamate}}{{Drugbox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| 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
| image = Ethynylestradiol 3-sulfate.svg
| width = 250px
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =
| class = Estrogen; Estrogen ester
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref =
| CAS_number = 24560-70-1
| CAS_supplemental =
| ATC_prefix =
| ATC_suffix =
| ATC_supplemental =
| PubChem = 68575
| IUPHAR_ligand =
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 61845
| UNII = 67P0FM71OZ
| KEGG =
| ChEBI = 136600
| ChEMBL = 1614648
| synonyms = EE sulfate; 17α-Ethynylestradiol 3-sulfate
| C=20 | H=24 | O=5 | S=1
| molecular_weight = 376.467 g/mol
| 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_Ref =
| 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_Ref =
| 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.[1][2][3] EE sulfate can be transformed back into EE 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][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.[4] However, other studies have suggested that EE sulfate may nonetheless contribute up to 20% of total EE levels.[2][5]

See also

  • List of estrogen esters § Esters of other steroidal estrogens

References

1. ^{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 Suppl 1 | issue = | pages = 3–63 | year = 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | url = http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf}}
2. ^{{cite book|author1=Michael Oettel|author2=Ekkehard Schillinger|title=Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen|url=https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA284|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-60107-1|pages=284–285,290}}
3. ^{{cite journal | vauthors = Fotherby K | title = Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy | journal = Contraception | volume = 54 | issue = 2 | pages = 59–69 | date = August 1996 | pmid = 8842581 | doi = 10.1016/0010-7824(96)00136-9 | url = }}
4. ^{{cite book|author1=Donna Shoupe|author2=Florence P. Haseltine|title=Contraception|url=https://books.google.com/books?id=cpDhBwAAQBAJ&pg=PA19|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4612-2730-4|pages=19–}}
5. ^{{cite journal | vauthors = Mattison DR, Karyakina N, Goodman M, LaKind JS | title = Pharmaco- and toxicokinetics of selected exogenous and endogenous estrogens: a review of the data and identification of knowledge gaps | journal = Crit. Rev. Toxicol. | volume = 44 | issue = 8 | pages = 696–724 | date = September 2014 | pmid = 25099693 | doi = 10.3109/10408444.2014.930813 | url = }}
{{Estrogen receptor modulators}}{{Steroid-stub}}{{Genito-urinary-drug-stub}}

8 : Alkynes|Diols|Estranes|Estrogen esters|Human drug metabolites|Prodrugs|Sulfates|Synthetic estrogens

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