Estrone
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| Non-proprietary name | Estrone | ||||||||||||||||||
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| Molecular formula | C 18 H 22 O 2 | ||||||||||||||||||
| Brief description |
colorless crystals |
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| Molar mass | 270.36 g · mol -1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
261-264 ° C |
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| solubility |
practically insoluble in water (30 mg l −1 at 20 ° C) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Estrone (E 1 ) is a natural estrogen . The biosynthesis of estrone takes place via the aromatization and demethylation of androstenedione using the enzyme aromatase .
It was first isolated around 1930 by Adolf Butenandt and independently of Edward Adelbert Doisy .
effect
In women in the so-called fertile years, only 45% of the estrone in the blood comes from the ovary and 5% from the adrenal gland, but 50% comes from other sources (extraglandular), especially the subcutaneous fatty tissue. There it is chemically converted from a male hormone ( androstenedione ). This explains why estrone does not have as pronounced an effect on the cycle as estradiol - except for polycystic ovary syndrome and obesity. In patients with PCO and / or overweight , higher and “more rigid” estrone concentrations are found in the blood. The resulting negative reaction on the pituitary gland disrupts the central release of LH and FSH , which also messes up the entire hormone control system. In postmenopausal women, 95% of the estrone is formed almost exclusively from the hormone DHEA and androstenedione of the ovary and the adrenal cortex. This is then chemically converted in the fat cells. The direct production of estrone and estradiol in the ovary, however, is very low at this age. Women in early menopause may have relatively higher concentrations of estrone despite low blood estradiol levels. This can, for example, reduce the need for hormone replacement therapy (HRT). But it can also be an important finding in connection with bleeding disorders or chest pain. A special feature arises in connection with estrogen tablets (oral therapy): During the intestinal and liver passage, the artificial “tablet estrogens” are converted to a large extent by the liver into estrone. This leads to unnaturally high levels of estrone in the blood. Since estrone and estradiol are constantly being converted into one another in the body, signs of an estradiol overdose (e.g. tension in the chest or water retention) and an underdosage of estradiol (e.g. renewed menopausal symptoms: so-called escape phenomenon) can occur ). If a woman who takes estrogen tablets has very high estrone values, the therapy should be switched to natural estrogens, which are administered through the skin (gels or plasters). In men, the blood concentrations of estrone are higher than that of estradiol, because men have twice as high levels of DHEA in the blood compared to women, which act as a precursor of androstenedione and thus also of estrone. Particularly high estrone values are to be expected in people with an overactivity of a certain enzyme ( aromatase ). This is mainly due to high alcohol consumption, obesity and fatty liver. The effects in men can then be erectile dysfunction, breast enlargement and an increase in belly fat (visceral obesity).
Use in chemical synthesis
The drug ethinylestradiol can be obtained from estrone by introducing an ethynyl group in position 17 .
Web links
- Jassal / reactome: Adrostenedione is converted to estrone by Aromatase (CYP19A1)
Individual evidence
- ↑ a b c Entry on estrone. In: Römpp Online . Georg Thieme Verlag, accessed on December 22, 2014.
- ↑ Data sheet Estron at Acros, accessed on February 22, 2010.
- ↑ a b Estrone data sheet at Sigma-Aldrich , accessed on March 31, 2011 ( PDF ).
- ^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , Thieme-Verlag Stuttgart, 5th edition (2009), pp. 522-523 ISBN 978-3-13-558405-8 .