 | |
| Clinical data | |
|---|---|
| Trade names | Esmopal |
| Other names | Estradiol monopalmitate; Estradiol hexadecanoate; Estradiol 17β-hexadecanoate |
| Drug class | Estrogen;Estrogen ester |
| Identifiers | |
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| CAS Number | |
| PubChemCID | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.024.819 |
| Chemical and physical data | |
| Formula | C34H54O3 |
| Molar mass | 510.803 g·mol−1 |
| 3D model (JSmol) | |
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Estradiol palmitate (brand nameEsmopal), orestradiol monopalmitate, also known asestradiol 17β-hexadecanoate, is anaturally occurring[1]steroidalestrogen and anestrogen ester – specifically, the C17βpalmitateester ofestradiol.[2] It occurs in the body as a very long-lastingmetabolite andprohormone of estradiol.[1] The compound has noaffinity for theestrogen receptor, requiringtransformation into estradiol for its estrogenic activity.[3] In addition to its endogenous role, estradiol palmitate was formerly used as a fattening agent inchickens under the brand name Esmopal.[4][5][6][7][8]
| Estrogen | Other names | RBATooltip Relative binding affinity (%)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 viain-vitro displacement oflabeledestradiol fromestrogen receptors (ERs) generally ofrodentuterinecytosol.Estrogen esters are variablyhydrolyzed 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 fromhalf-maximal effective concentrations (EC50) that were determined viain-vitroβ‐galactosidase (β-gal) andgreen fluorescent protein (GFP)productionassays inyeast expressing humanERα and humanERβ. Bothmammaliancells and yeast have the capacity to hydrolyze estrogen esters.c = The affinities ofestradiol cypionate for the ERs are similar to those ofestradiol valerate andestradiol benzoate (figure).Sources: See template page. | ||||||
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