Epimestrol

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = (8R,9S,13S,14S,16R,17S)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-16,17-diol

| image = Epimestrol.png

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| tradename = Alene, Stimovul

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| routes_of_administration = By mouth

| class = Estrogen; Estrogen ether

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| CAS_number_Ref =

| CAS_number = 7004-98-0

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| ATC_prefix = G03

| ATC_suffix = GB03

| PubChem = 244809

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| ChemSpiderID_Ref =

| ChemSpiderID = 214111

| UNII = 7IVE3SDZ38

| KEGG = D04021

| synonyms = Stimovul; ORG-817; NSC-55975; 3-Methoxyestriol; 3-Methoxy-17-epiestriol

| C=19 | H=26 | O=3

| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@H]2O)O)CCC4=C3C=CC(=C4)OC

| StdInChI_Ref =

| StdInChI = 1S/C19H26O3/c1-19-8-7-14-13-6-4-12(22-2)9-11(13)3-5-15(14)16(19)10-17(20)18(19)21/h4,6,9,14-18,20-21H,3,5,7-8,10H2,1-2H3/t14-,15-,16+,17-,18-,19+/m1/s1

| StdInChIKey_Ref =

| StdInChIKey = UHQGCIIQUZBJAE-RRQVMCLOSA-N

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Epimestrol ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|BAN|British Approved Name}}) (brand names Alene, Stimovul; former developmental code name ORG-817), also known as 3-methoxy-17-epiestriol, is a synthetic, steroidal estrogen and an estrogen ether and prodrug of 17-epiestriol.{{cite book|author=G.W.A. Milne|title=Ashgate Handbook of Endocrine Agents and Steroids|url=https://books.google.com/books?id=GFM8DwAAQBAJ&pg=PT25|date=1 November 2017|publisher=Taylor & Francis|isbn=978-1-351-74347-1|pages=25–}}NLM [https://www.ncbi.nlm.nih.gov/mesh/?term=Epimestrol MESH entry for Epimestrol]{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA391|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=391–}} It has been used as a component of ovulation induction in combination with gonadotropin-releasing hormone.{{cite journal | vauthors = Maia H, Barbosa I, Maia H, Nascimento AJ, Bonfim de Souza M | title = Induction of ovulation with epimestrol and luteinizing hormone-releasing hormone (LH-RH) | journal = Int J Gynaecol Obstet | volume = 17 | issue = 5 | pages = 431–3 | year = 1980 | pmid = 6103833 | doi = 10.1002/j.1879-3479.1980.tb00179.x| s2cid = 22761848 }}