4-Methoxyestrone

4-Methoxyestrone (4-ME1) is an endogenous, naturally occurring methoxylated catechol estrogen and metabolite of estrone that is formed by catechol O-methyltransferase via the intermediate 4-hydroxyestrone.[1][2][3] It has estrogenic activity similarly to estrone and 4-hydroxyestrone.[4]

Selected biological properties of endogenous estrogens in rats
EstrogenER RBA (%)Uterine weight (%)UterotrophyLH levels (%)SHBG RBA (%)
Control100100
Estradiol100506 ± 20+++12–19100
Estrone11 ± 8490 ± 22+++?20
Estriol10 ± 4468 ± 30+++8–183
Estetrol0.5 ± 0.2?Inactive?1
17α-Estradiol4.2 ± 0.8????
2-Hydroxyestradiol24 ± 7285 ± 8+b31–6128
2-Methoxyestradiol0.05 ± 0.04101Inactive?130
4-Hydroxyestradiol45 ± 12????
4-Methoxyestradiol1.3 ± 0.2260++?9
4-Fluoroestradiola180 ± 43?+++??
2-Hydroxyestrone1.9 ± 0.8130 ± 9Inactive110–1428
2-Methoxyestrone0.01 ± 0.00103 ± 7Inactive95–100120
4-Hydroxyestrone11 ± 4351++21–5035
4-Methoxyestrone0.13 ± 0.04338++65–9212
16α-Hydroxyestrone2.8 ± 1.0552 ± 42+++7–24<0.5
2-Hydroxyestriol0.9 ± 0.3302+b??
2-Methoxyestriol0.01 ± 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.
4-Methoxyestrone
Names
IUPAC name
(8R,9S,13S,14S)-3-Hydroxy-4-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
Other names
4-ME1; 4-MeOE1; 4-MeO-E1; 4-Hydroxyestrone 4-methyl ether; 3-Hydroxy-4-methoxyestra-1,3,5(10)-trien-17-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
Properties
C19H24O3
Molar mass 300.398 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References

  1. http://www.hmdb.ca/metabolites/HMDB60088
  2. Hemnes AR (16 December 2015). Gender, Sex Hormones and Respiratory Disease: A Comprehensive Guide. Humana Press. pp. 32–. ISBN 978-3-319-23998-9.
  3. Lauritzen C, Studd JW (22 June 2005). Current Management of the Menopause. CRC Press. pp. 378–379. ISBN 978-0-203-48612-2.
  4. Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK (2000). "Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women". Journal of the Society for Gynecologic Investigation. 7 (3): 175–83. doi:10.1016/s1071-5576(00)00049-6. PMID 10865186.


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