From Wikipedia, the free encyclopedia
Chemical compound
Estradiol palmitate
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Trade names | Esmopal |
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Other names | Estradiol monopalmitate; Estradiol hexadecanoate; Estradiol 17β-hexadecanoate |
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Drug class |
Estrogen;
Estrogen ester |
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[(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
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CAS Number | |
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PubChem
CID | |
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ChemSpider | |
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UNII | |
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CompTox Dashboard (
EPA) | |
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ECHA InfoCard |
100.024.819
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Formula | C34H54O3 |
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Molar mass | 510.803 g·mol−1 |
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3D model (
JSmol) | |
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CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C
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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
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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]
See also
References
- ^
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.
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Estrogens |
ERTooltip Estrogen receptor agonists |
- Steroidal:
Alfatradiol
- Certain
androgens/
anabolic steroids (e.g.,
testosterone,
testosterone esters,
methyltestosterone,
metandienone,
nandrolone esters) (via estrogenic metabolites)
- Certain
progestins (e.g.,
norethisterone,
noretynodrel,
etynodiol diacetate,
tibolone)
-
Clomestrone
-
Cloxestradiol acetate
-
Conjugated estriol
-
Conjugated estrogens
-
Epiestriol
-
Epimestrol
-
Esterified estrogens
-
Estetrol†
-
Estradiol
-
Estradiol esters (e.g.,
estradiol acetate,
estradiol benzoate,
estradiol cypionate,
estradiol enanthate,
estradiol undecylate,
estradiol valerate,
polyestradiol phosphate,
estradiol ester mixtures (
Climacteron))
-
Estramustine phosphate
-
Estriol
-
Estriol esters (e.g.,
estriol succinate,
polyestriol phosphate)
-
Estrogenic substances
-
Estrone
-
Estrone esters
-
Ethinylestradiol#
-
Hydroxyestrone diacetate
-
Mestranol
-
Methylestradiol
-
Moxestrol
-
Nilestriol
-
Prasterone (dehydroepiandrosterone; DHEA)
-
Promestriene
-
Quinestradol
-
Quinestrol
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Progonadotropins | |
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Antiestrogens |
ERTooltip Estrogen receptor antagonists (incl.
SERMsTooltip selective estrogen receptor modulators/
SERDsTooltip selective estrogen receptor downregulators) | |
---|
Aromatase inhibitors | |
---|
Antigonadotropins |
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Androgens/
anabolic steroids (e.g.,
testosterone,
testosterone esters,
nandrolone esters,
oxandrolone,
fluoxymesterone)
-
D2 receptor
antagonists (
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domperidone,
metoclopramide,
risperidone,
haloperidol,
chlorpromazine,
sulpiride)
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GnRH agonists (e.g.,
leuprorelin,
goserelin)
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GnRH antagonists (e.g.,
cetrorelix,
elagolix)
-
Progestogens (e.g.,
chlormadinone acetate,
cyproterone acetate,
gestonorone caproate,
hydroxyprogesterone caproate,
medroxyprogesterone acetate,
megestrol acetate)
|
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Others | |
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|
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|
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ERTooltip Estrogen receptor | Agonists |
- Steroidal:
2-Hydroxyestradiol
-
2-Hydroxyestrone
-
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
-
3α-Androstanediol
-
3α,5α-Dihydrolevonorgestrel
-
3β,5α-Dihydrolevonorgestrel
-
3α-Hydroxytibolone
-
3β-Hydroxytibolone
-
3β-Androstanediol
-
4-Androstenediol
-
4-Androstenedione
-
4-Fluoroestradiol
-
4-Hydroxyestradiol
-
4-Hydroxyestrone
-
4-Methoxyestradiol
-
4-Methoxyestrone
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5-Androstenediol
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7-Oxo-DHEA
-
7α-Hydroxy-DHEA
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7α-Methylestradiol
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7β-Hydroxyepiandrosterone
-
8,9-Dehydroestradiol
-
8,9-Dehydroestrone
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8β-VE2
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10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
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11β-Chloromethylestradiol
-
11β-Methoxyestradiol
-
15α-Hydroxyestradiol
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-
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-
16α-Fluoroestradiol
-
16α-Hydroxy-DHEA
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16α-Iodoestradiol
-
16α-LE2
-
16β-Hydroxyestrone
-
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
-
17α-Estradiol (
alfatradiol)
-
17α-Dihydroequilenin
-
17α-Dihydroequilin
-
17α-Epiestriol (16α-hydroxy-17α-estradiol)
-
17α-Ethynyl-3α-androstanediol
-
17α-Ethynyl-3β-androstanediol
-
17β-Dihydroequilenin
-
17β-Dihydroequilin
-
17β-Methyl-17α-dihydroequilenin
-
Abiraterone
-
Abiraterone acetate
-
Alestramustine
-
Almestrone
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Anabolic steroids (e.g.,
testosterone and
esters,
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metandienone (methandrostenolone),
nandrolone and
esters, many others; via estrogenic metabolites)
-
Atrimustine
-
Bolandiol
-
Bolandiol dipropionate
-
Butolame
-
Clomestrone
-
Cloxestradiol
-
Conjugated estriol
-
Conjugated estrogens
-
Cyclodiol
-
Cyclotriol
-
DHEA
-
DHEA-S
-
ent-Estradiol
-
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
-
Epimestrol
-
Equilenin
-
Equilin
-
ERA-63 (ORG-37663)
-
Esterified estrogens
-
Estetrol
-
Estradiol
-
Estramustine
-
Estramustine phosphate
-
Estrapronicate
-
Estrazinol
-
Estriol
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Estrogenic substances
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Etynodiol
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Hippulin
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Lynestrenol
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Mestranol
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Methylestradiol
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Moxestrol
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Mytatrienediol
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Nilestriol
-
Norethisterone
-
Noretynodrel
-
Orestrate
-
Pentolame
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Prodiame
-
Prolame
-
Promestriene
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RU-16117
-
Quinestradol
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Quinestrol
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Tibolone
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anethole,
anol,
dianethole,
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EGCG,
epicatechin,
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formononetin,
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genistin,
glycitein,
kaempferol,
liquiritigenin,
mirificin,
myricetin,
naringenin,
penduletin,
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prunetin,
puerarin,
quercetin,
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campesterol,
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Steroid-like (e.g.,
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agnuside,
rotundifuran)
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Mixed (
SERMsTooltip Selective estrogen receptor modulators) | |
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Antagonists |
- Coregulator-binding modulators:
ERX-11
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GPERTooltip G protein-coupled estrogen receptor | Agonists | |
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Antagonists | |
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Unknown | |
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