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Chemical compound
EBCO
Other names EBCO; Estradiol 3-benzoate 17β-cyclooctenyl ether
Routes of administration
By mouth
[1]
Drug class
Estrogen ;
Estrogen ester ;
Estrogen ether
[(8R ,9S ,13S ,14S ,17S )-17-[(1E )-cycloocten-1-yl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a ]phenanthren-3-yl] benzoate
CAS Number
PubChem
CID
ChemSpider
Formula C 33 H 40 O 3
Molar mass 484.680 g·mol−1 3D model (
JSmol )
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O/C/4=C/CCCCCC4)CCC5=C3C=CC(=C5)OC(=O)C6=CC=CC=C6
InChI=1S/C33H40O3/c1-33-21-20-28-27-17-15-26(36-32(34)23-10-6-5-7-11-23)22-24(27)14-16-29(28)30(33)18-19-31(33)35-25-12-8-3-2-4-9-13-25/h5-7,10-12,15,17,22,28-31H,2-4,8-9,13-14,16,18-21H2,1H3/b25-12+/t28-,29-,30+,31+,33+/m1/s1
Key:DOFNLZKUGHVIMH-UQWKGHMASA-N
Estradiol benzoate cyclooctenyl ether (EBCO ), or estradiol 3-benzoate 17β-cyclooctenyl ether , is a
synthetic
estrogen as well as
estrogen ester and
ether – specifically, the C3
benzoate
ester and C17β
cyclooctenyl
ether of
estradiol – which was described in the early 1970s and was never marketed.
[1]
[2]
[3]
[4] It has been found to have a dramatically prolonged
duration of action with
oral administration in animals, similarly to the related compound
quinestrol (the 3-cyclopentyl ether of
ethinylestradiol ).
[1]
[5]
[6] A single oral dose of EBCO sustained high
uterus weights for 3 weeks in rats.
[1] This long-lasting activity may be due to storage of EBCO in
fat .
[1] It appears that EBCO is
absorbed satisfactorily from the
gastrointestinal tract , at least partially survives
first-pass metabolism in the
liver and
intestines , and is then sequestered into fat, from which it is slowly released and activated into estradiol.
[1] In contrast to quinestrol, the oral activity of EBCO is greatly improved when it is delivered in an
oil solution as opposed to an
aqueous vehicle .
[1]
See also
References
ER Tooltip Estrogen receptor
Agonists
Steroidal:
2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
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17α-Ethynyl-3α-androstanediol
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SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
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ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown