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{{Use dmy dates|date=August 2018}}
{{Chembox

| ImageFile = Estrone 3-glucuronide.svg
| ImageClass = skin-invert
| ImageSize = 225px
| ImageAlt =

| IUPACName = 17-Oxoestra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acid
| SystematicName = (2''S'',3''S'',4''S'',5''R'',6''S'')-3,4,5-Trihydroxy-6-<nowiki/>{[(3a''S'',3b''R'',9b''S'',11a''S'')-11a-methyl-1-oxo-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1''H''-cyclopenta[''a'']phenanthren-7-yl]oxy}oxane-2-carboxylic acid
| OtherNames = Estrone 3-glucuronide; Estrone 3-D-glucuronide; Estra-1,3,5(10)-triene-3-ol-17-one 3-D-glucuronoside

| Section1 = {{Chembox Identifiers
| CASNo = 2479-90-5
| ChEBI =
| ChEMBL = 1232444
| ChemSpiderID = 103124
| KEGG = C11133
| PubChem = 115255
| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O
| StdInChI = 1S/C24H30O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-16,18-21,23,26-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,18+,19+,20-,21+,23-,24+/m1/s1
| StdInChIKey = FJAZVHYPASAQKM-JBAURARKSA-N
| UNII = 933Q277TO2
}}
| Section2 = {{Chembox Properties
| C=24 | H=30 | O=8
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}

'''Estrone glucuronide''', or '''estrone-3-D-glucuronide''', is a [[conjugation (biochemistry)|conjugated]] [[metabolite]] of [[estrone]].<ref name="HMDB">{{Cite web|url=http://www.hmdb.ca/metabolites/HMDB04483|title = Human Metabolome Database: Showing metabocard for Estrone glucuronide (HMDB0004483)}}</ref> It is formed from estrone in the [[liver]] by [[UDP-glucuronyltransferase]] via attachment of [[glucuronic acid]] and is eventually [[excretion|excreted]] in the [[urine]] by the [[kidney]]s.<ref name="HMDB" /> It has much higher [[water solubility]] than does estrone.<ref name="HMDB" /> Glucuronides are the most abundant estrogen conjugates and estrone glucuronide is the dominant metabolite of estradiol.<ref name="HMDB" />

When [[exogenous]] estradiol is administered [[oral administration|orally]], it is subject to extensive [[first-pass metabolism]] (95%) in the [[intestine]]s and [[liver]].<ref name="OettelSchillinger2012">{{cite book| first1 = Michael | last1 = Oettel | first2 = Ekkehard | last2 = Schillinger | name-list-style = vanc | title = Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen|url=https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA268|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-60107-1|pages=268–}}</ref><ref name="LauritzenStudd2005">{{cite book|first1 = Christian | last1 = Lauritzen | first2 = John W. W. | last2 = Studd | name-list-style = vanc |title=Current Management of the Menopause|url=https://books.google.com/books?id=WD7S7677xUUC&pg=PA364|date=22 June 2005|publisher=CRC Press|isbn=978-0-203-48612-2|pages=364–}}</ref> A single administered dose of estradiol is [[absorption (pharmacokinetics)|absorbed]] 15% as [[estrone]], 25% as [[estrone sulfate]], 25% as [[estradiol glucuronide]], and 25% as estrone glucuronide.<ref name="OettelSchillinger2012" /> Formation of [[estrogen]] glucuronide conjugates is particularly important with oral estradiol as the percentage of estrogen glucuronide conjugates in circulation is much higher with oral ingestion than with [[parenteral]] estradiol.<ref name="OettelSchillinger2012" /> Estrone glucuronide can be reconverted back into estradiol, and a large circulating pool of estrogen glucuronide and sulfate conjugates serves as a long-lasting reservoir of estradiol that effectively extends its [[terminal half-life]] of oral estradiol.<ref name="OettelSchillinger2012" /><ref name="LauritzenStudd2005" /> In demonstration of the importance of first-pass metabolism and the estrogen conjugate reservoir in the [[pharmacokinetics]] of estradiol,<ref name="OettelSchillinger2012" /> the terminal half-life of oral estradiol is 13 to 20 hours<ref name="StanczykArcher2013">{{cite journal | vauthors = Stanczyk FZ, Archer DF, Bhavnani BR | title = Ethinyl estradiol and 17β-estradiol in combined oral contraceptives: pharmacokinetics, pharmacodynamics and risk assessment | journal = Contraception | volume = 87 | issue = 6 | pages = 706–27 | date = June 2013 | pmid = 23375353 | doi = 10.1016/j.contraception.2012.12.011 }}</ref> whereas with [[intravenous injection]] its terminal half-life is only about 1 to 2 hours.<ref name="pmid7169965">{{cite journal | vauthors = Düsterberg B, Nishino Y | title = Pharmacokinetic and pharmacological features of oestradiol valerate | journal = Maturitas | volume = 4 | issue = 4 | pages = 315–24 | date = December 1982 | pmid = 7169965 | doi = 10.1016/0378-5122(82)90064-0}}</ref>

{{Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors}}

{{Estradiol metabolism|align=right}}

==See also==
* [[Catechol estrogen]]
* [[Estradiol sulfate]]
* [[Estriol glucuronide]]
* [[Estriol sulfate]]
* [[Estrogen conjugate]]
* [[Lipoidal estrogen]]

==References==
{{Reflist}}

== External links ==
* [http://www.hmdb.ca/metabolites/HMDB04483 Metabocard of Estrone Glucuronide – Human Metabolome Database]

{{Steroid hormones}}
{{Estrogen receptor modulators}}

[[Category:Estranes]]
[[Category:Estrogens]]
[[Category:Estrone esters]]
[[Category:Glucuronide esters]]
[[Category:Human metabolites]]

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