Estrone glucuronide
| Estrone glucuronide | |
|---|---|
| Estrone 3-glucuronide.svg | |
17-Oxoestra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acid | |
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{[(3aS,3bR,9bS,11aS)-11a-methyl-1-oxo-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}oxane-2-carboxylic acid | |
別称 Estrone 3-glucuronide; Estrone 3-D-glucuronide; Estra-1,3,5(10)-triene-3-ol-17-one 3-D-glucuronoside | |
| Identifiers | |
| 2479-90-5 | |
| ChEMBL | ChEMBL1232444 |
| ChemSpider | 103124 |
| |
| Jmol-3D images | Image |
| KEGG | C11133 |
| PubChem | 115255 |
| |
| UNII | 933Q277TO2 |
| Properties | |
| C24H30O8 | |
| Molar mass | 446.496 g·mol−1 |
| 特記なき場合、データは常温（25 °C）・常圧（100 kPa）におけるものである。 | |
Estrone glucuronide, or estrone-3-D-glucuronide, is a conjugated metabolite of estrone.[1] It is formed from estrone in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by the kidneys.[1] It has much higher water solubility than does estrone.[1] Glucuronides are the most abundant estrogen conjugates and estrone glucuronide is the dominant metabolite of estradiol.[1]
When exogenous estradiol is administered orally, it is subject to extensive first-pass metabolism (95%) in the intestines and liver.[2][3] A single administered dose of estradiol is absorbed 15% as estrone, 25% as estrone sulfate, 25% as estradiol glucuronide, and 25% as estrone glucuronide.[2] 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.[2] 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.[2][3] In demonstration of the importance of first-pass metabolism and the estrogen conjugate reservoir in the pharmacokinetics of estradiol,[2] the terminal half-life of oral estradiol is 13 to 20 hours[4] whereas with intravenous injection its terminal half-life is only about 1 to 2 hours.[5]
Metabolic pathways of estradiol in humans
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See also
- Catechol estrogen
- Estradiol sulfate
- Estriol glucuronide
- Estriol sulfate
- Estrogen conjugate
- Lipoidal estrogen
References
- ↑ 以下の位置に戻る: 1.0 1.1 1.2 1.3 "Human Metabolome Database: Showing metabocard for Estrone glucuronide (HMDB0004483)".
- ↑ 以下の位置に戻る: 2.0 2.1 2.2 2.3 2.4 Oettel M, Schillinger E (6 12月 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp. 268–. ISBN 978-3-642-60107-1.
- ↑ 以下の位置に戻る: 3.0 3.1 Lauritzen C, Studd JW (22 6月 2005). Current Management of the Menopause. CRC Press. pp. 364–. ISBN 978-0-203-48612-2.
- ↑ Stanczyk FZ, Archer DF, Bhavnani BR (6月 2013). "Ethinyl estradiol and 17β-estradiol in combined oral contraceptives: pharmacokinetics, pharmacodynamics and risk assessment". Contraception. 87 (6): 706–27. doi:10.1016/j.contraception.2012.12.011. PMID 23375353.
- ↑ Düsterberg B, Nishino Y (12月 1982). "Pharmacokinetic and pharmacological features of oestradiol valerate". Maturitas. 4 (4): 315–24. doi:10.1016/0378-5122(82)90064-0. PMID 7169965.
External links
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