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Estradiol palmitate

January 01, 1970

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]

Estradiol palmitate
Clinical data
Trade namesEsmopal
Other namesEstradiol monopalmitate; Estradiol hexadecanoate; Estradiol 17β-hexadecanoate
Drug classEstrogen; Estrogen ester
Identifiers
  • [(8R,9S,13S,14S,17S)-3-Hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] hexadecanoate
CAS Number
  • 5776-45-4
PubChem CID
  • 111095
ChemSpider
  • 99723
UNII
  • 1Q5Y448XT0
CompTox Dashboard (EPA)
  • DTXSID00973346
ECHA InfoCard100.024.819
Chemical and physical data
FormulaC34H54O3
Molar mass510.803 g·mol−1
3D model (JSmol)
  • Interactive image
  • CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C
  • InChI=1S/C34H54O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-33(36)37-32-22-21-31-30-19-17-26-25-27(35)18-20-28(26)29(30)23-24-34(31,32)2/h18,20,25,29-32,35H,3-17,19,21-24H2,1-2H3/t29-,30-,31+,32+,34+/m1/s1
  • Key:XQKLZLWOOGGXMV-KWXXMMNJSA-N
Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors
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 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 edit

References edit

  1. ^ a b Hochberg RB, Pahuja SL, Larner JM, Zielinski JE (1990). "Estradiol-fatty acid esters. Endogenous long-lived estrogens". Annals of the New York Academy of Sciences. 595 (1): 74–92. Bibcode:1990NYASA.595...74H. doi:10.1111/j.1749-6632.1990.tb34284.x. PMID 2197972. S2CID 19866729.
  2. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 898. ISBN 978-1-4757-2085-3.
  3. ^ Janocko L, Larner JM, Hochberg RB (April 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. PMID 6705734.
  4. ^ Gerrits RJ (March 1970). "The Influence of Hormones on the Production of Meat". Sci Teacher. 37 (3): 31–34. JSTOR 24151460.
  5. ^ Gardiner EE, Newberry RC, Hunt JR (January 1988). "Effect of estradiol-17 beta-monopalmitate on the incidence of sudden death syndrome in male broiler chickens". Poultry Science. 67 (1): 156–157. doi:10.3382/ps.0670156. PMID 3375173.
  6. ^ Bassila MK, Adams RL, Pratt DE, Stadelman WJ (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.
  7. ^ Moran ET, Etches RJ (June 1983). "Finishing broiler toms using an estradiol 17 beta implant together with a high energy-low protein final feed". Poultry Science. 62 (6): 1010–1020. doi:10.3382/ps.0621010. PMID 6878131.
  8. ^ Mickelberry WC (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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January 01, 1970
estradiol, palmitate, brand, name, esmopal, estradiol, monopalmitate, also, known, estradiol, 17β, hexadecanoate, naturally, occurring, steroidal, estrogen, estrogen, ester, specifically, c17β, palmitate, ester, estradiol, occurs, body, very, long, lasting, me. Estradiol palmitate brand name Esmopal or estradiol monopalmitate also known as estradiol 17b hexadecanoate is a naturally occurring 1 steroidal estrogen and an estrogen ester specifically the C17b 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 Estradiol palmitateClinical dataTrade namesEsmopalOther namesEstradiol monopalmitate Estradiol hexadecanoate Estradiol 17b hexadecanoateDrug classEstrogen Estrogen esterIdentifiersIUPAC name 8R 9S 13S 14S 17S 3 Hydroxy 13 methyl 6 7 8 9 11 12 14 15 16 17 decahydrocyclopenta a phenanthren 17 yl hexadecanoateCAS Number5776 45 4PubChem CID111095ChemSpider99723UNII1Q5Y448XT0CompTox Dashboard EPA DTXSID00973346ECHA InfoCard100 024 819Chemical and physical dataFormulaC 34H 54O 3Molar mass510 803 g mol 13D model JSmol Interactive imageSMILES CCCCCCCCCCCCCCCC O O C H 1CC C H 2 C H 3CCc4cc O ccc4 C H 3CC C 12CInChI InChI 1S C34H54O3 c1 3 4 5 6 7 8 9 10 11 12 13 14 15 16 33 36 37 32 22 21 31 30 19 17 26 25 27 35 18 20 28 26 29 30 23 24 34 31 32 2 h18 20 25 29 32 35H 3 17 19 21 24H2 1 2H3 t29 30 31 32 34 m1 s1Key XQKLZLWOOGGXMV KWXXMMNJSA N vte Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors Estrogen Other names RBATooltip Relative binding affinity a REP b ER ERa ERb 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 17b glucuronide E2 17G 0 002 0 0002 Estradiol benzoate EB Estradiol 3 benzoate 10 1 1 0 52 Estradiol 17b acetate E2 17A 31 45 24 Estradiol diacetate EDA Estradiol 3 17b diacetate 0 79 Estradiol propionate EP Estradiol 17b propionate 19 26 2 6 Estradiol valerate EV Estradiol 17b valerate 2 11 0 04 21 Estradiol cypionate EC Estradiol 17b cypionate c 4 0 Estradiol palmitate Estradiol 17b palmitate 0 Estradiol stearate Estradiol 17b 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 lt 0 001 0 0006 Ethinylestradiol EE 17a 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 gt 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 b galactosidase b gal and green fluorescent protein GFP production assays in yeast expressing human ERa and human ERb 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 editEstradiol stearate Estradiol undecylate List of estrogen esters Estradiol estersReferences edit a b Hochberg RB Pahuja SL Larner JM Zielinski JE 1990 Estradiol fatty acid esters Endogenous long lived estrogens Annals of the New York Academy of Sciences 595 1 74 92 Bibcode 1990NYASA 595 74H doi 10 1111 j 1749 6632 1990 tb34284 x PMID 2197972 S2CID 19866729 Elks J 14 November 2014 The Dictionary of Drugs Chemical Data Chemical Data Structures and Bibliographies Springer p 898 ISBN 978 1 4757 2085 3 Janocko L Larner JM Hochberg RB April 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 PMID 6705734 Gerrits RJ March 1970 The Influence of Hormones on the Production of Meat Sci Teacher 37 3 31 34 JSTOR 24151460 Gardiner EE Newberry RC Hunt JR January 1988 Effect of estradiol 17 beta monopalmitate on the incidence of sudden death syndrome in male broiler chickens Poultry Science 67 1 156 157 doi 10 3382 ps 0670156 PMID 3375173 Bassila MK Adams RL Pratt DE Stadelman WJ 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 ET Etches RJ June 1983 Finishing broiler toms using an estradiol 17 beta implant together with a high energy low protein final feed Poultry Science 62 6 1010 1020 doi 10 3382 ps 0621010 PMID 6878131 Mickelberry WC 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 nbsp This drug article relating to the genito urinary system is a stub You can help Wikipedia by expanding it vte nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Estradiol palmitate amp oldid 1176353729, wikipedia, wiki, book, books, library,

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