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Statements

Subject Item
dbr:List_of_estrogen_esters
dbo:wikiPageWikiLink
dbr:Estradiol_sulfate
Subject Item
dbr:List_of_estrogens
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dbr:Estradiol_sulfate
Subject Item
dbr:Pharmacokinetics_of_estradiol
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dbr:Estradiol_sulfate
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dbr:C18H24O5S
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dbr:Estradiol_sulfate
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dbr:Estriol_glucuronide
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dbr:Estradiol_sulfate
Subject Item
dbr:Estrogen_ester
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dbr:Estradiol_sulfate
Subject Item
dbr:Organosulfate
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dbr:Estradiol_sulfate
Subject Item
dbr:Estradiol
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dbr:Estradiol_sulfate
Subject Item
dbr:Estradiol_3-glucuronide
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dbr:Estradiol_sulfate
Subject Item
dbr:Estradiol_glucuronide
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dbr:Estradiol_sulfate
Subject Item
dbr:Estradiol_sulfate
rdf:type
owl:Thing wikidata:Q11173 n14:ChemicalObject dbo:ChemicalSubstance dbo:ChemicalCompound
rdfs:label
Estradiol sulfate
rdfs:comment
Estradiol sulfate (E2S), or 17β-estradiol 3-sulfate, is a natural, endogenous steroid and an estrogen ester. E2S itself is biologically inactive, but it can be converted by steroid sulfatase (also called estrogen sulfatase) into estradiol, which is a potent estrogen. Simultaneously, estrogen sulfotransferases convert estradiol to E2S, resulting in an equilibrium between the two steroids in various tissues. Estrone and E2S are the two immediate metabolic sources of estradiol. E2S can also be metabolized into estrone sulfate (E1S), which in turn can be converted into estrone and estradiol. Circulating concentrations of E2S are much lower than those of E1S. High concentrations of E2S are present in breast tissue, and E2S has been implicated in the biology of breast cancer via serving as an ac
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n11:Estradiol_sulfate.svg
dcterms:subject
dbc:Phenol_esters dbc:Human_metabolites dbc:Estradiol_esters dbc:Sulfate_esters
dbo:wikiPageID
50875728
dbo:wikiPageRevisionID
1120786591
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dbr:Conjugated_estrogens dbr:Pregnenolone_sulfate dbr:Estradiol dbc:Human_metabolites dbr:Conjugation_(biochemistry) dbr:Lipoidal_estradiol dbc:Phenol_esters dbr:Natural_product dbr:Salt_(chemistry) dbr:In_vivo dbr:Premarin dbr:In_vitro dbc:Estradiol_esters dbr:Chemical_equilibrium dbr:Catechol_estrogen dbr:Oral_administration dbr:Estrogen_ester dbr:Sodium dbr:Estrogen_(medication) dbr:Estrogen_conjugate dbr:Breast_cancer dbr:Metabolite dbr:Estrogen dbr:Glutathione dbr:Endogenous dbr:Precursor_(biochemistry) dbr:Prodrug dbr:Steroid dbr:Dehydroepiandrosterone_sulfate dbr:Enzyme dbr:Breast dbr:Enzyme_inhibitor dbr:Estrogen_sulfotransferase dbc:Sulfate_esters dbr:Estrone_sulfate dbr:Estrone dbr:Potency_(pharmacology) dbr:Ovulation dbr:Estrogen_receptor dbr:List_of_estrogen_esters dbr:Estriol_sulfate dbr:Estradiol_glucuronide dbr:Uterotrophic dbr:Pharmaceutical_drug dbr:Steroid_hormone_receptor dbr:Conjugated_equine_estrogen dbr:Glutathione_S-transferase dbr:Steroid_sulfatase
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wikidata:Q24887704 yago-res:Estradiol_sulfate n17:2Lza9
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dbt:Structural_properties_of_selected_estradiol_esters dbt:Estrogens_and_antiestrogens dbt:Reflist dbt:Steroid_hormones dbt:Affinities_and_estrogenic_potencies_of_estrogen_esters_and_ethers_at_the_estrogen_receptors dbt:Estrogen_receptor_modulators dbt:Chembox_Hazards dbt:Chembox_Identifiers dbt:Estradiol dbt:Chembox dbt:Chembox_Properties
dbo:thumbnail
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dbp:imagefile
Estradiol sulfate.svg
dbp:imagesize
225
dbp:othernames
Estra-1,3,5-triene-3,17β-diol 3-sulfate
dbp:pin
-1
dbo:abstract
Estradiol sulfate (E2S), or 17β-estradiol 3-sulfate, is a natural, endogenous steroid and an estrogen ester. E2S itself is biologically inactive, but it can be converted by steroid sulfatase (also called estrogen sulfatase) into estradiol, which is a potent estrogen. Simultaneously, estrogen sulfotransferases convert estradiol to E2S, resulting in an equilibrium between the two steroids in various tissues. Estrone and E2S are the two immediate metabolic sources of estradiol. E2S can also be metabolized into estrone sulfate (E1S), which in turn can be converted into estrone and estradiol. Circulating concentrations of E2S are much lower than those of E1S. High concentrations of E2S are present in breast tissue, and E2S has been implicated in the biology of breast cancer via serving as an active reservoir of estradiol. As the sodium salt, sodium estradiol sulfate, E2S is present as a minor constituent (0.9%) of conjugated equine estrogens (CEEs), or Premarin. It effectively functions as a prodrug to estradiol in this preparation, similarly to E1S. E2S is also formed as a metabolite of estradiol, as well as of estrone and E1S. Aside from its presence in CEEs, E2S is not available as a commercial pharmaceutical drug. E2S shows about 10,000-fold lower potency in activating the estrogen receptors relative to estradiol in vitro. It is 10-fold less potent than estrone sulfate orally in terms of in vivo uterotrophic effect in rats. Estrogen sulfates like estradiol sulfate or estrone sulfate are about twice as potent as the corresponding free estrogens in terms of estrogenic effect when given orally to rodents. This in part led to the introduction of conjugated estrogens (Premarin), which are primarily estrone sulfate, in 1941. Although inactive at steroid hormone receptors, E2S has been found to act as a potent inhibitor of glutathione S-transferase, an enzyme that contributes to the inactivation of estradiol via conversion of it into an estradiol-glutathione conjugate. As such, E2S can indirectly serve as a positive effector of estrogen signaling. Estradiol levels are about 1.5- to 4-fold higher than E2S levels in women. This is in contrast to E1S, the levels of which are about 10 to 15 times higher than those of estrone. E2S at an oral dosage of 5 mg/day in women resulted in inhibition of ovulation in 89% of cycles (47 of 53).
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dbo:alternativeName
Estra-1,3,5(10)-triene-3,17β-diol 3-sulfate
dbo:iupacName
(1S,3aS,3bR,9bS,11aS)-1-Hydroxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-7-yl hydrogen sulfate
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dbr:Estramustine_phosphate
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dbr:Estrone_glucuronide
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dbr:Estrone_sulfate
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dbr:Estrone_sulfotransferase
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dbr:Steroid_sulfotransferase
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dbr:Steroid_sulfate
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dbr:17β-Estradiol_3-sulfate
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dbr:17β-Estradiol_sulfate
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dbr:17β-estradiol_3-sulfate
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dbr:17β-estradiol_sulfate
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Subject Item
dbr:Sodium_estradiol_sulfate
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Subject Item
dbr:E2S
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dbr:Estradiol_3-sulfate
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dbr:Estradiol_sodium_sulfate
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dbr:Estradiol_sulfate_sodium
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