Estradiol palmitate
Estradiol palmitate (brand name Esmopal), or estradiol monopalmitate, also known as estradiol 17β-hexadecanoate, is a naturally occurring[1] steroidal estrogen and an estrogen ester – specifically, the C17β palmitate ester of estradiol.[2] It occurs in the body as a very long-lasting metabolite and prohormone of estradiol.[1] The compound has no affinity for the estrogen receptor, requiring transformation into estradiol for its estrogenic activity.[3] In addition to its endogenous role, estradiol palmitate was formerly used as a fattening agent in chickens under the brand name Esmopal.[4][5][6][7][8]
| 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. | ||||||
 | |
| 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 | |
| PubChem CID | |
| 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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References
- Hochberg RB, Pahuja SL, Larner JM, Zielinski JE (1990). "Estradiol-fatty acid esters. Endogenous long-lived estrogens". Ann. N. Y. Acad. Sci. 595 (1): 74–92. Bibcode:1990NYASA.595...74H. doi:10.1111/j.1749-6632.1990.tb34284.x. PMID 2197972. S2CID 19866729.
- J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 898. ISBN 978-1-4757-2085-3.
- Janocko, Laura; Larner, Janice M.; Hochberg, Richard B. (1984). "The Interaction of C-17 Esters of Estradiol with the Estrogen Receptor*". Endocrinology. 114 (4): 1180–1186. doi:10.1210/endo-114-4-1180. ISSN 0013-7227. PMID 6705734.
- Gerrits, R. J. (1970). The Influence of Hormones on the Production of Meat. Sci Teacher.
- Gardiner EE, Newberry RC, Hunt JR (1988). "Effect of estradiol-17 beta-monopalmitate on the incidence of sudden death syndrome in male broiler chickens". Poult. Sci. 67 (1): 156–7. doi:10.3382/ps.0670156. PMID 3375173.
- Bassila, M. K.; Adams, R. L.; Pratt, D. E.; Stadelman, W. J. (1975). "Effects of Sex, Strain and Estrogens on Quality of Chicken Roasters". Poultry Science. 54 (3): 696–702. doi:10.3382/ps.0540696. ISSN 0032-5791.
- Moran, E. T.; Etches, R. J. (1983). "Finishing Broiler Toms Using an Estradiol 17 Implant Together with a High Energy-Low Protein Final Feed". Poultry Science. 62 (6): 1010–1020. doi:10.3382/ps.0621010. ISSN 0032-5791. PMID 6878131.
- Mickelberry, W. C. (1968). "Influence of Dietary Fats and Estradiol 17 Beta Monopalmitate Upon the Edible Meat Yield of Roaster Chickens". Poultry Science. 47 (4): 1254–1257. doi:10.3382/ps.0471254. ISSN 0032-5791.
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