Estriol dihexanoate

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]

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
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
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC30H44O5
Molar mass484.677 g·mol−1
3D model (JSmol)
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
InChI
  • 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

See also

References
  1. Michael Oettel; Ekkehard Schillinger (6 December 2012). 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". Chem. Pharm. Bull. 11 (4): 510–514. doi:10.1248/cpb.11.510. PMID 13994597.
  3. Heithecker R, Aedo AR, Landgren BM, Cekan SZ (1991). "Plasma estriol levels after intramuscular injection of estriol and two of its esters". Horm. Res. 35 (6): 234–8. doi:10.1159/000181911. PMID 1819548.


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