Estriol dihexanoate

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = [(8R,9S,13S,14S,16R,17R)-3-hexanoyloxy-16-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] hexanoate

| image = Estriol 3,17-dihexanoate.svg

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| routes_of_administration = Intramuscular injection

| class = Estrogen; Estrogen ester

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| CAS_number = 104202-96-2

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| UNII = J2K5XW8K72

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| PubChem = 128509

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| ChemSpiderID = 113906

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| synonyms = Oestriol dihexanoate; Estriol 3,17β-dihexanoate; 16α-Hydroxyestra-1,3,5(10)-triene-3,17β-diyl dihexanoate

| C=30 | H=44 | O=5

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

| StdInChI_Ref =

| StdInChI = 1S/C30H44O5/c1-4-6-8-10-27(32)34-21-13-15-22-20(18-21)12-14-24-23(22)16-17-30(3)25(24)19-26(31)29(30)35-28(33)11-9-7-5-2/h13,15,18,23-26,29,31H,4-12,14,16-17,19H2,1-3H3/t23-,24-,25+,26-,29+,30+/m1/s1

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| StdInChIKey = ZOVABFBGAYSQTL-AECPDVIXSA-N

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Estriol dihexanoate, or estriol 3,17β-dihexanoate, is a synthetic estrogen and estrogen ester – specifically, the C3 and C17β dihexanoate ester of estriol – which was first described in 1963 and was never marketed.{{cite book| vauthors = Kuhnz W, Blode H, Zimmermann H | chapter = Pharmacokinetics of 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=PA273 |date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-60107-1|pages=273–}}{{cite journal | vauthors = Tsuneda K, Yamada J, Yasuda K, Mori H | title = Preparation of some estriol esters | journal = Chemical & Pharmaceutical Bulletin | volume = 11 | issue = 4 | pages = 510–514 | date = April 1963 | pmid = 13994597 | doi = 10.1248/cpb.11.510 | doi-access = free }}{{cite journal | vauthors = Heithecker R, Aedo AR, Landgren BM, Cekan SZ | title = Plasma estriol levels after intramuscular injection of estriol and two of its esters | journal = Hormone Research | volume = 35 | issue = 6 | pages = 234–238 | date = 1991 | pmid = 1819548 | doi = 10.1159/000181911 }} Following a single intramuscular injection of 8.90 mg estriol dihexanoate (equivalent to 5.0 mg estriol) in an oil solution, peak levels of estriol occurred after 2.1 to 3.4 days, an elimination half-life of 187 to 221 hours was observed, and estriol levels remained elevated for up to 20 to 50 days. For comparison, the durations of estriol and estriol dipropionate were far shorter.