Estradiol palmitateのソースを表示

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| IUPAC_name = [(8''R'',9''S'',13''S'',14''S'',17''S'')-3-Hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[''a'']phenanthren-17-yl] hexadecanoate
| image = Estradiol palmitate structure.svg
| width = 250px

<!--Clinical data-->
| tradename = Esmopal
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| legal_US = 
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| routes_of_administration = 
| class = [[Estrogen (medication)|Estrogen]]; [[Estrogen ester]]

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
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<!--Identifiers-->
| CAS_number_Ref = 
| CAS_number = 5776-45-4
| CAS_supplemental = 
| ATC_prefix = 
| ATC_suffix = 
| PubChem = 111095
| DrugBank_Ref = 
| DrugBank = 
| ChemSpiderID_Ref = 
| ChemSpiderID = 99723
| UNII = 1Q5Y448XT0
| synonyms = Estradiol monopalmitate; Estradiol hexadecanoate; Estradiol 17β-hexadecanoate

<!--Chemical data-->
| C=34 | H=54 | O=3
| SMILES = CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C
| StdInChI_Ref = 
| StdInChI = 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
| StdInChIKey_Ref = 
| StdInChIKey = XQKLZLWOOGGXMV-KWXXMMNJSA-N
}}

'''Estradiol palmitate''' (brand name '''Esmopal'''), or '''estradiol monopalmitate''', also known as '''estradiol 17β-hexadecanoate''', is a [[natural product|naturally occurring]]<ref name="pmid2197972">{{cite journal | vauthors = Hochberg RB, Pahuja SL, Larner JM, Zielinski JE | title = Estradiol-fatty acid esters. Endogenous long-lived estrogens | journal = Annals of the New York Academy of Sciences | volume = 595 | issue = 1 | pages = 74–92 | year = 1990 | pmid = 2197972 | doi = 10.1111/j.1749-6632.1990.tb34284.x | s2cid = 19866729 | bibcode = 1990NYASA.595...74H }}</ref> [[steroid]]al [[estrogen]] and an [[estrogen ester]] – specifically, the C17β [[palmitate]] [[ester]] of [[estradiol]].<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=RA1-PA129|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|page=898}}</ref> It occurs in the body as a very long-lasting [[metabolite]] and [[prohormone]] of estradiol.<ref name="pmid2197972" /> The compound has no [[affinity (pharmacology)|affinity]] for the [[estrogen receptor]], requiring [[biotransformation|transformation]] into estradiol for its estrogenic activity.<ref name="JanockoLarner1984">{{cite journal | vauthors = Janocko L, Larner JM, Hochberg RB | title = The interaction of C-17 esters of estradiol with the estrogen receptor | journal = Endocrinology | volume = 114 | issue = 4 | pages = 1180–1186 | date = April 1984 | pmid = 6705734 | doi = 10.1210/endo-114-4-1180 }}</ref> In addition to its endogenous role, estradiol palmitate was formerly used as a fattening agent in [[chicken]]s under the brand name Esmopal.<ref name="Gerrits1970">{{cite journal | vauthors = Gerrits RJ | date = March 1970 | url = https://www.jstor.org/stable/24151460 | title = The Influence of Hormones on the Production of Meat. | journal = Sci Teacher | volume = 37 | issue = 3 | pages = 31–34 | jstor = 24151460 }}</ref><ref name="pmid3375173">{{cite journal | vauthors = Gardiner EE, Newberry RC, Hunt JR | title = Effect of estradiol-17 beta-monopalmitate on the incidence of sudden death syndrome in male broiler chickens | journal = Poultry Science | volume = 67 | issue = 1 | pages = 156–157 | date = January 1988 | pmid = 3375173 | doi = 10.3382/ps.0670156 | doi-access = free }}</ref><ref name="BassilaAdams1975">{{cite journal| vauthors = Bassila MK, Adams RL, Pratt DE, Stadelman WJ |title=Effects of Sex, Strain and Estrogens on Quality of Chicken Roasters|journal=Poultry Science|volume=54|issue=3|year=1975|pages=696–702|issn=0032-5791|doi=10.3382/ps.0540696|doi-access=free}}</ref><ref name="MoranEtches1983">{{cite journal | vauthors = Moran ET, Etches RJ | title = Finishing broiler toms using an estradiol 17 beta implant together with a high energy-low protein final feed | journal = Poultry Science | volume = 62 | issue = 6 | pages = 1010–1020 | date = June 1983 | pmid = 6878131 | doi = 10.3382/ps.0621010 | doi-access = free }}</ref><ref name="Mickelberry1968">{{cite journal| vauthors = Mickelberry WC |title=Influence of Dietary Fats and Estradiol 17 Beta Monopalmitate Upon the Edible Meat Yield of Roaster Chickens|journal=Poultry Science|volume=47|issue=4|year=1968|pages=1254–1257|issn=0032-5791|doi=10.3382/ps.0471254|doi-access=free}}</ref>

{{Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors}}

== See also ==
* [[Estradiol stearate]]
* [[Estradiol undecylate]]
* [[List of estrogen esters#Estradiol esters|List of estrogen esters § Estradiol esters]]

== References ==
{{Reflist}}

{{Estradiol}}
{{Estrogens and antiestrogens}}
{{Estrogen receptor modulators}}

[[Category:Abandoned drugs]]
[[Category:Estradiol esters]]
[[Category:Palmitate esters]]
[[Category:Veterinary drugs]]

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{{Steroid-stub}}