词条 | Ethinylestradiol sulfate |
释义 |
| 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
References1. ^1 2 3 {{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}} {{Estrogen receptor modulators}}{{Steroid-stub}}{{Genito-urinary-drug-stub}}2. ^1 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. ^1 2 {{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. ^1 {{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 = }} 8 : Alkynes|Diols|Estranes|Estrogen esters|Human drug metabolites|Prodrugs|Sulfates|Synthetic estrogens |
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