Estradiol diacetate (EDA), or estradiol 3,17β-diacetate, is an estrogen and an estrogen ester—specifically, the C3 and C17β diacetate ester of estradiol—which was never marketed.[1][2][3][4] It is related to the estradiol monoesters estradiol acetate (estradiol 3-acetate; Femtrace) and estradiol 17β-acetate.[1][4]
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| Clinical data | |
|---|---|
| Other names | EDA; Estradiol 3,17β-diacetate; NSC-106559 |
| Drug class | Estrogen; Estrogen ester |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.020.306 |
| Chemical and physical data | |
| Formula | C22H28O4 |
| Molar mass | 356.462 g·mol−1 |
| 3D model (JSmol) | |
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| Estrogen | Other names | RBA (%)a | REP (%)b | |||
|---|---|---|---|---|---|---|
| ER | ERα | ERβ | ||||
| Estradiol | E2 | 100 | 100 | 100 | ||
| Estradiol 3-sulfate | E2S; E2-3S | ? | 0.02 | 0.04 | ||
| Estradiol 3-glucuronide | E2-3G | ? | 0.02 | 0.09 | ||
| Estradiol 17β-glucuronide | E2-17G | ? | 0.002 | 0.0002 | ||
| Estradiol benzoate | EB; Estradiol 3-benzoate | 10 | 1.1 | 0.52 | ||
| Estradiol 17β-acetate | E2-17A | 31–45 | 24 | ? | ||
| Estradiol diacetate | EDA; Estradiol 3,17β-diacetate | ? | 0.79 | ? | ||
| Estradiol propionate | EP; Estradiol 17β-propionate | 19–26 | 2.6 | ? | ||
| Estradiol valerate | EV; Estradiol 17β-valerate | 2–11 | 0.04–21 | ? | ||
| Estradiol cypionate | EC; Estradiol 17β-cypionate | ?c | 4.0 | ? | ||
| Estradiol palmitate | Estradiol 17β-palmitate | 0 | ? | ? | ||
| Estradiol stearate | Estradiol 17β-stearate | 0 | ? | ? | ||
| Estrone | E1; 17-Ketoestradiol | 11 | 5.3–38 | 14 | ||
| Estrone sulfate | E1S; Estrone 3-sulfate | 2 | 0.004 | 0.002 | ||
| Estrone glucuronide | E1G; Estrone 3-glucuronide | ? | <0.001 | 0.0006 | ||
| Ethinylestradiol | EE; 17α-Ethynylestradiol | 100 | 17–150 | 129 | ||
| Mestranol | EE 3-methyl ether | 1 | 1.3–8.2 | 0.16 | ||
| Quinestrol | EE 3-cyclopentyl ether | ? | 0.37 | ? | ||
| Footnotes: a = Relative binding affinities (RBAs) were determined via in-vitro displacement of labeled estradiol from estrogen receptors (ERs) generally of rodent uterine cytosol. Estrogen esters are variably hydrolyzed into estrogens in these systems (shorter ester chain length -> greater rate of hydrolysis) and the ER RBAs of the esters decrease strongly when hydrolysis is prevented. b = Relative estrogenic potencies (REPs) were calculated from half-maximal effective concentrations (EC50) that were determined via in-vitro β‐galactosidase (β-gal) and green fluorescent protein (GFP) production assays in yeast expressing human ERα and human ERβ. Both mammalian cells and yeast have the capacity to hydrolyze estrogen esters. c = The affinities of estradiol cypionate for the ERs are similar to those of estradiol valerate and estradiol benzoate (figure). Sources: See template page. | ||||||
See also
editReferences
edit- ^ a b Junkmann K, Witzel H (1957). "Chemie und Pharmakologie von Steroidhormon-Estern" [Chemistry and pharmacology of steroid hormone esters]. Z Vitam Horm Fermentforsch (in German). 9 (1–2): 97–143 contd. PMID 13531579.
- ^ Janocko L, Larner JM, Hochberg RB (April 1984). "The interaction of C-17 esters of estradiol with the estrogen receptor". Endocrinology. 114 (4): 1180–6. doi:10.1210/endo-114-4-1180. PMID 6705734.
- ^ Mu Y, Peng S, Zhang A, Wang L (February 2011). "Role of pocket flexibility in the modulation of estrogen receptor alpha by key residue arginine 394". Environ. Toxicol. Chem. 30 (2): 330–6. doi:10.1002/etc.389. PMID 21038436. S2CID 22116062.
- ^ a b Friedrich W. Derz, ed. (1976). ChemPRODUCTindex, Volumes 1-2. De Gruyter. pp. 881–. ISBN 978-3-11-002141-7. OCLC 2619908.
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