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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
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| CAS_number = 104202-96-2
| CAS_number = 104202-96-2
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| UNII_Ref = {{fdacite|correct|FDA}}
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| UNII = J2K5XW8K72
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<!--Chemical data-->
| C=30 | H=44 | O=5
| C=30 | H=44 | O=5
| molecular_weight = 484.677 g/mol
| 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
| 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
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'''Estriol dihexanoate''', or '''estriol 3,17β-dihexanoate''', is a [[synthetic compound|synthetic]] [[estrogen (medication)|estrogen]] and [[estrogen ester]] – specifically, the C3 and C17β [[hexanoate|dihexanoate]] [[ester]] of [[estriol (medication)|estriol]] – which was first described in 1963 and was never marketed.<ref name="OettelSchillinger2012">{{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=PA273|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-60107-1|pages=273–}}</ref><ref name="pmid13994597">{{cite journal | vauthors = Tsuneda K, Yamada J, Yasuda K, Mori H | title = Preparation of some estriol esters | journal = Chem. Pharm. Bull. | volume = 11 | issue = | pages = 510–514 | date = April 1963 | pmid = 13994597 | doi = 10.1248/cpb.11.510 | url = https://www.jstage.jst.go.jp/article/cpb1958/11/4/11_4_510/_article| doi-access = free }}</ref><ref name="pmid1819548">{{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 = Horm. Res. | volume = 35 | issue = 6 | pages = 234–8 | date = 1991 | pmid = 1819548 | doi = 10.1159/000181911 | url = }}</ref> Following a single [[intramuscular injection]] of 8.90&nbsp;mg estriol dihexanoate (equivalent to 5.0&nbsp;mg estriol) in an [[oil solution]], [[Cmax (pharmacology)|peak levels]] of estriol occurred after 2.1 to 3.4&nbsp;days, an [[elimination half-life]] of 187 to 221&nbsp;hours was observed, and estriol levels remained elevated for up to 20 to 50&nbsp;days.<ref name="OettelSchillinger2012" /><ref name="pmid1819548" /> For comparison, the [[duration of action|duration]]s of estriol and [[estriol dipropionate]] were far shorter.<ref name="OettelSchillinger2012" /><ref name="pmid1819548" />
'''Estriol dihexanoate''', or '''estriol 3,17β-dihexanoate''', is a [[synthetic compound|synthetic]] [[estrogen (medication)|estrogen]] and [[estrogen ester]] – specifically, the C3 and C17β [[hexanoate|dihexanoate]] [[ester]] of [[estriol (medication)|estriol]] – which was first described in 1963 and was never marketed.<ref name="OettelSchillinger2012">{{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–}}</ref><ref name="pmid13994597">{{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 }}</ref><ref name="pmid1819548">{{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 }}</ref> Following a single [[intramuscular injection]] of 8.90&nbsp;mg estriol dihexanoate (equivalent to 5.0&nbsp;mg estriol) in an [[oil solution]], [[Cmax (pharmacology)|peak levels]] of estriol occurred after 2.1 to 3.4&nbsp;days, an [[elimination half-life]] of 187 to 221&nbsp;hours was observed, and estriol levels remained elevated for up to 20 to 50&nbsp;days.<ref name="OettelSchillinger2012" /><ref name="pmid1819548" /> For comparison, the [[duration of action|duration]]s of estriol and [[estriol dipropionate]] were far shorter.<ref name="OettelSchillinger2012" /><ref name="pmid1819548" />


==See also==
== See also ==
* [[List of estrogen esters#Estriol esters|List of estrogen esters § Estriol esters]]
* [[List of estrogen esters#Estriol esters|List of estrogen esters § Estriol esters]]


==References==
== References ==
{{Reflist}}
{{Reflist}}


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[[Category:Abandoned drugs]]
[[Category:Abandoned drugs]]
[[Category:Caproate esters]]
[[Category:Caproate esters]]
[[Category:Estranes]]
[[Category:Estriol esters]]
[[Category:Estriol esters]]
[[Category:Prodrugs]]
[[Category:Synthetic estrogens]]
[[Category:Synthetic estrogens]]
[[Category:Triols]]
[[Category:Secondary alcohols]]



{{Steroid-stub}}
{{Steroid-stub}}

Latest revision as of 15:58, 29 December 2023

Estriol dihexanoate
Clinical data
Other namesOestriol dihexanoate; Estriol 3,17β-dihexanoate; 16α-Hydroxyestra-1,3,5(10)-triene-3,17β-diyl dihexanoate
Routes of
administration		Intramuscular injection
Drug classEstrogen; Estrogen ester
Identifiers
  • [(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
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC30H44O5
Molar mass484.677 g·mol−1
3D model (JSmol)
  • 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
  • InChI=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
  • Key:ZOVABFBGAYSQTL-AECPDVIXSA-N

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.[1][2][3] 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.[1][3] For comparison, the durations of estriol and estriol dipropionate were far shorter.[1][3]

See also

[edit]

References

[edit]
  1. ^ a b c Kuhnz W, Blode H, Zimmermann H (6 December 2012). "Pharmacokinetics of exogenous natural and synthetic estrogens and antiestrogens". In Oettel M, Schillinger E (eds.). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp. 273–. ISBN 978-3-642-60107-1.
  2. ^ Tsuneda K, Yamada J, Yasuda K, Mori H (April 1963). "Preparation of some estriol esters". Chemical & Pharmaceutical Bulletin. 11 (4): 510–514. doi:10.1248/cpb.11.510. PMID 13994597.
  3. ^ a b c Heithecker R, Aedo AR, Landgren BM, Cekan SZ (1991). "Plasma estriol levels after intramuscular injection of estriol and two of its esters". Hormone Research. 35 (6): 234–238. doi:10.1159/000181911. PMID 1819548.
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