2-Methoxyestriol
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| Names | |
|---|---|
| IUPAC name 2-Methoxyestra-1,3,5(10)-triene-3,16α,17β-triol | |
| Systematic IUPAC name (1R,2R,3aS,3bR,9bS,11aS)-8-Methoxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,2,7-triol | |
| Other names 2-MeO-E3 | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C19H26O4 | |
| Molar mass | 318.413 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
2-Methoxyestriol (2-MeO-E3) is an endogenous estrogen metabolite.[1][2][3] It is specifically a metabolite of estriol and 2-hydroxyestriol.[1][2][3] It has negligible affinity for the estrogen receptors and no estrogenic activity.[4] However, 2-methoxyestriol does have some non-estrogen receptor-mediated cholesterol-lowering effects.[5]
| Estrogen | ER RBA (%) | Uterine weight (%) | Uterotrophy | LH levels (%) | SHBG RBA (%) |
|---|---|---|---|---|---|
| Control | – | 100 | – | 100 | – |
| Estradiol (E2) | 100 | 506 ± 20 | +++ | 12–19 | 100 |
| Estrone (E1) | 11 ± 8 | 490 ± 22 | +++ | ? | 20 |
| Estriol (E3) | 10 ± 4 | 468 ± 30 | +++ | 8–18 | 3 |
| Estetrol (E4) | 0.5 ± 0.2 | ? | Inactive | ? | 1 |
| 17α-Estradiol | 4.2 ± 0.8 | ? | ? | ? | ? |
| 2-Hydroxyestradiol | 24 ± 7 | 285 ± 8 | +b | 31–61 | 28 |
| 2-Methoxyestradiol | 0.05 ± 0.04 | 101 | Inactive | ? | 130 |
| 4-Hydroxyestradiol | 45 ± 12 | ? | ? | ? | ? |
| 4-Methoxyestradiol | 1.3 ± 0.2 | 260 | ++ | ? | 9 |
| 4-Fluoroestradiola | 180 ± 43 | ? | +++ | ? | ? |
| 2-Hydroxyestrone | 1.9 ± 0.8 | 130 ± 9 | Inactive | 110–142 | 8 |
| 2-Methoxyestrone | 0.01 ± 0.00 | 103 ± 7 | Inactive | 95–100 | 120 |
| 4-Hydroxyestrone | 11 ± 4 | 351 | ++ | 21–50 | 35 |
| 4-Methoxyestrone | 0.13 ± 0.04 | 338 | ++ | 65–92 | 12 |
| 16α-Hydroxyestrone | 2.8 ± 1.0 | 552 ± 42 | +++ | 7–24 | <0.5 |
| 2-Hydroxyestriol | 0.9 ± 0.3 | 302 | +b | ? | ? |
| 2-Methoxyestriol | 0.01 ± 0.00 | ? | Inactive | ? | 4 |
| Notes: Values are mean ± SD or range. ER RBA = Relative binding affinity to estrogen receptors of rat uterine cytosol. Uterine weight = Percentage change in uterine wet weight of ovariectomized rats after 72 hours with continuous administration of 1 μg/hour via subcutaneously implanted osmotic pumps. LH levels = Luteinizing hormone levels relative to baseline of ovariectomized rats after 24 to 72 hours of continuous administration via subcutaneous implant. Footnotes: a = Synthetic (i.e., not endogenous). b = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: See template. | |||||
See also
[edit]References
[edit]- ^ a b Fishman J, Gallagher TF (October 1958). "2-Methoxyestriol: a new metabolite of estradiol in man". Arch. Biochem. Biophys. 77 (2): 511–3. doi:10.1016/0003-9861(58)90097-3. PMID 13584013.
- ^ a b King RJ (May 1961). "Oestriol metabolism by rat- and rabbit-liver slices. Isolation of 2-methoxyoestriol and 2-hydroxyestriol". Biochem. J. 79 (2): 355–61. doi:10.1042/bj0790355. PMC 1205847. PMID 13756104.
- ^ a b Fujii Y, Teranishi M, Nakada K, Yamazaki M, Kishida S, Miyabo S (September 1988). "Radioimmunoassay of 2-methoxyestriol in pregnancy plasma". Horm. Metab. Res. 20 (9): 599–600. doi:10.1055/s-2007-1010895. PMID 3198067. S2CID 260170130.
- ^ Martucci CP (July 1983). "The role of 2-methoxyestrone in estrogen action". J. Steroid Biochem. 19 (1B): 635–8. doi:10.1016/0022-4731(83)90229-7. PMID 6310247.
- ^ Kono, Shinzo; Higa, Hiroaki; Sunagawa, Hajime (1989). "Hypocholesterolemic Effect of Long-Term Continuous Administration of 2-Methoxyestriol in Dietary Hypercholesterolemic Rats". Journal of Clinical Biochemistry and Nutrition. 6 (1): 49–56. doi:10.3164/jcbn.6.49. ISSN 1880-5086.
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