Estradiol benzoate cyclooctenyl ether (original) (raw)
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. 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). A single oral dose of EBCO sustained high uterus weights for 3 weeks in rats. This long-lasting activity may be due to storage of EBCO in fat. It appears that EBCO is absorbed satisfactorily from the gastrointestinal tract, at least partially survives first-pass metabolism in the liver and intestines,
| Property | Value |
|---|---|
| dbo:abstract | 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. 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). A single oral dose of EBCO sustained high uterus weights for 3 weeks in rats. This long-lasting activity may be due to storage of EBCO in fat. 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. 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. (en) |
| dbo:casNumber | 28200-94-4 |
| dbo:class | dbr:Estrogen_(medication) dbr:Estrogen_ester dbr:Estrogen_ether |
| dbo:pubchem | 6436089 |
| dbo:thumbnail | wiki-commons:Special:FilePath/Estradiol_benzoate_cyclooctenyl_ether.svg?width=300 |
| dbo:wikiPageID | 57753344 (xsd:integer) |
| dbo:wikiPageLength | 5509 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1120785526 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Quinestrol dbr:List_of_estrogen_esters dbr:Uterus dbc:Abandoned_drugs dbc:Benzoate_esters dbc:Estrogen_ethers dbc:Prodrugs dbc:Synthetic_estrogens dbr:Ester dbr:Estrogen_(medication) dbr:Estrogen_ester dbr:Gastrointestinal_tract dbr:Oral_administration dbr:Liver dbr:Adipose_tissue dbr:Cyclooctane dbr:Estradiol_(medication) dbr:Ethinylestradiol dbr:Absorption_(pharmacokinetics) dbc:Estradiol_esters dbr:Ether dbr:Intestine dbr:Oil_solution dbr:Estrogen_ether dbr:Duration_of_action dbr:Aqueous_vehicle dbr:First-pass_metabolism dbr:Synthetic_compound dbr:Benzoate |
| dbp:c | 33 (xsd:integer) |
| dbp:casNumber | 28200 (xsd:integer) |
| dbp:chemspiderid | 4940765 (xsd:integer) |
| dbp:class | dbr:Estrogen_(medication) dbr:Estrogen_ester dbr:Estrogen_ether |
| dbp:drugName | EBCO (en) |
| dbp:h | 40 (xsd:integer) |
| dbp:iupacName | [-17-[-cycloocten-1-yl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate (en) |
| dbp:o | 3 (xsd:integer) |
| dbp:pubchem | 6436089 (xsd:integer) |
| dbp:routesOfAdministration | dbr:Oral_administration |
| dbp:smiles | C[C@]12CC[C@H]3[C@H]CCC5=C3C=CCOCC6=CC=CC=C6 (en) |
| dbp:stdinchi | 1 (xsd:integer) |
| dbp:stdinchikey | DOFNLZKUGHVIMH-UQWKGHMASA-N (en) |
| dbp:synonyms | EBCO; Estradiol 3-benzoate 17β-cyclooctenyl ether (en) |
| dbp:width | 250 (xsd:integer) |
| dbp:wikiPageUsesTemplate | dbt:Drugbox dbt:Estrogen_receptor_modulators dbt:Genito-urinary-drug-stub dbt:Reflist dbt:Short_description dbt:Steroid-stub dbt:Estradiol |
| dcterms:subject | dbc:Abandoned_drugs dbc:Benzoate_esters dbc:Estrogen_ethers dbc:Prodrugs dbc:Synthetic_estrogens dbc:Estradiol_esters |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 dbo:Drug |
| rdfs:comment | 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. 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). A single oral dose of EBCO sustained high uterus weights for 3 weeks in rats. This long-lasting activity may be due to storage of EBCO in fat. It appears that EBCO is absorbed satisfactorily from the gastrointestinal tract, at least partially survives first-pass metabolism in the liver and intestines, (en) |
| rdfs:label | Estradiol benzoate cyclooctenyl ether (en) |
| owl:sameAs | wikidata:Estradiol benzoate cyclooctenyl ether https://global.dbpedia.org/id/6T1dd |
| prov:wasDerivedFrom | wikipedia-en:Estradiol_benzoate_cyclooctenyl_ether?oldid=1120785526&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/Estradiol_benzoate_cyclooctenyl_ether.svg |
| foaf:isPrimaryTopicOf | wikipedia-en:Estradiol_benzoate_cyclooctenyl_ether |
| foaf:name | EBCO (en) |
| is dbo:wikiPageRedirects of | dbr:C33H40O3 dbr:Estradiol_3-benzoate_17β-cyclooctenyl_ether |
| is dbo:wikiPageWikiLink of | dbr:List_of_estrogen_esters dbr:C33H40O3 dbr:EBCO dbr:Estradiol_3-benzoate_17β-cyclooctenyl_ether |
| is foaf:primaryTopic of | wikipedia-en:Estradiol_benzoate_cyclooctenyl_ether |
