ethinylestradiol sulfate

{{Short description|Chemical compound}}

{{Distinguish|Ethinylestradiol sulfonate|Ethinylestradiol sulfamate}}

{{Infobox drug

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| 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

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| class = Estrogen; Estrogen ester

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| CAS_number_Ref =

| CAS_number = 24560-70-1

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| PubChem = 68575

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| 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

| 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.{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | issue = Suppl 1 | pages = 3–63 | date = August 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 }}{{cite book| vauthors = Kuhnz W, Blade H, Zimmermann H | chapter = Pharmacokinetics and Exogenous Natural and Synthetic Estrogens and Antiestrogens | veditors = Oettel M, Schillinger E |title=Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen| chapter-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}}{{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 }} 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.{{cite journal | vauthors = Goldzieher JW, Mileikowsky G, Newburger J, Dorantes A, Stavchansky SA | title = Human pharmacokinetics of ethynyl estradiol 3-sulfate and 17-sulfate | journal = Steroids | volume = 51 | issue = 1–2 | pages = 63–79 | date = 1988 | pmid = 3242167 | doi = 10.1016/0039-128x(88)90185-7 | s2cid = 21188869 }}{{cite book| vauthors = Goldzieher JW | chapter = Pharmacology of Contraceptive Steroids| veditors = Shoupe D, Haseltine FP |title=Contraception| chapter-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–}} 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.{{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 = Critical Reviews in Toxicology | volume = 44 | issue = 8 | pages = 696–724 | date = September 2014 | pmid = 25099693 | doi = 10.3109/10408444.2014.930813 | s2cid = 11212469 }}