Estradiol palmitate

Estradiol palmitate
Clinical data

Trade names	Esmopal
Identifiers
IUPAC 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] hexadecanoate
CAS Number	5776-45-4
PubChem (CID)	111095
ChemSpider	99723
UNII	1Q5Y448XT0
Chemical and physical data
Formula	C₃₄H₅₄O₃
Molar mass	510.80 g·mol⁻¹
3D model (Jmol)	Interactive image
SMILES CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C
InChI 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

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] In addition, estradiol palmitate was formerly used as a fattening agent in chickens.^[3]^[4]^[5]^[6]^[7]

References

1 2 Hochberg RB, Pahuja SL, Larner JM, Zielinski JE (1990). "Estradiol-fatty acid esters. Endogenous long-lived estrogens". Ann. N. Y. Acad. Sci. 595: 74–92. PMID 2197972.
↑ 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.
↑ 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. 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.
↑ 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.

Estrogens and antiestrogens

Estrogens

ER agonists	Steroidal: Alfatradiol Certain androgenic-anabolic steroids (e.g., testosterone, testosterone esters, nandrolone, methyltestosterone, metandienone) (via estrogenic metabolites) Certain progestins (e.g., norethisterone, noretynodrel, etynodiol diacetate, tibolone) Clomestrone Cloxestradiol acetate Conjugated equine estrogens/esterified estrogens (Premarin) 8,9-Dehydroestrone sulfate 17α-Dihydroequilenin sulfate 17α-Dihydroequilin sulfate 17β-Dihydroequilenin sulfate 17β-Dihydroequilin sulfate Equilenin sulfate Equilin sulfate Epiestriol Epimestrol Estetrol^† Estradiol Estradiol acetate Estradiol benzoate Estradiol butyrylacetate Estradiol cypionate^# Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol hemihydrate Estradiol hemisuccinate (estradiol succinate) Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol palmitate Estradiol phenylpropionate Estradiol pivalate (trimethyl estradiol acetate) Estradiol propoxyphenylpropionate Estradiol stearate Estradiol undecylate Estradiol valerate Polyestradiol phosphate Estramustine Estriol Estriol diacetate benzoate Estriol glucuronide (Emmenin, Progynon) Estriol succinate Estriol tripropionate Estrone Estrone acetate Estrone sulfate Estropipate (piperazine estrone sulfate) Estrone tetraacetylglucoside Ethinyl estradiol^# Ethinyl estradiol sulfonate Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Nilestriol Promestriene Quinestradol Quinestrol Non-steroidal: Benzestrol Bifluranol Chlorotrianisene Dienestrol Dienestrol diacetate Diethylstilbestrol (stilbestrol) Diethylstilbestrol diacetate Diethylstilbestrol dilaurate Diethylstilbestrol dipalmitate (stilpalmitate) Diethylstilbestrol dipropionate Diethylstilbestrol disulfate Diethylstilbestrol monobenzyl ether Dimestrol (diethylstilbestrol dimethyl ether) Fosfestrol (diethylstilbestrol diphosphate) Mestilbol (diethylstilbestrol monomethyl ether) Doisynoestrol (fenocycline) Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate Methallenestril Methestrol dipropionate (promethestrol dipropionate) Paroxypropione Quadrosilan Zeranol

Progonadotropins	Antiandrogens (e.g., bicalutamide) GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin) Gonadotropins (e.g., FSH, LH)

Antiestrogens

ER antagonists (incl. SERMs/SERDs)	Acolbifene^† Anordrin Bazedoxifene (+conjugated equine estrogens) Broparestrol Clomifene^# Cyclofenil Enclomifene^† Epitiostanol Etacstil ^§ Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Raloxifene Tamoxifen^# Toremifene Exclusively antagonistic: Fulvestrant

Aromatase inhibitors	Non-selective: Aminoglutethimide Testolactone Selective: Anastrozole Exemestane Fadrozole Formestane Letrozole

Antigonadotropins	Androgens/anabolic steroids (e.g., testosterone, testosterone esters, nandrolone, oxandrolone, fluoxymesterone) D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride) GnRH agonists (e.g., leuprorelin, goserelin) GnRH antagonists (e.g., cetrorelix) Progestogens (e.g., chlormadinone acetate, cyproterone acetate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone acetate, megestrol acetate)

Others	Mixed mechanism of action: Danazol Gestrinone

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Androgens and antiandrogens • Progestogens and antiprogestogens • Glucocorticoids and antiglucocorticoids • Mineralocorticoids and antimineralocorticoids • Gonadotropins and GnRH

Estrogen receptor modulators

Agonists	Steroidal: 1-Keto-1,2,3,4-tetrahydrophenanthrene 3α-Androstanediol 3β-Androstanediol 3α-Hydroxytibolone 3β-Hydroxytibolone 4-Androstenediol 4-Androstenedione 4-Hydroxyestradiol 4-Hydroxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone 8,9-Dehydroestrone 8β-VE2 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodo-E2 16α-LE2 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17β-Dihydroequilenin 17β-Dihydroequilin Abiraterone Abiraterone acetate 17α-Estradiol (alfatradiol) Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Cloxestradiol acetate DHEA DHEA-S Digitoxin (digitalis) Diosgenin Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin Estetrol Estradiol Estradiol 3-propionate Estradiol benzoate Estradiol butyrate benzoate Estradiol butyrylacetate Estradiol cyclooctyl acetate Estradiol cypionate Estradiol decanoate Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol hemihydrate Estradiol hemisuccinate (estradiol succinate) Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol mustard Estradiol palmitate Estradiol pivalate (trimethyl estradiol acetate) Estradiol propoxyphenylpropionate Estradiol stearate Estradiol sulfate Estradiol undecylate Estradiol valerate Lipoidal estradiol Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol acetate benzoate Estriol glucuronide Estriol sodium succinate Estriol succinate Estriol triacetate Estriol tripropionate Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone sulfate Estrone tetraacetylglucoside Estropipate Etamestrol (eptamestrol) Ethinyl estradiol Ethinyl estradiol sulfonate Ethinyl estriol Etynodiol diacetate Guggulsterone Hexolame Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Noretynodrel Orestrate Pentolame Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Polyestradiol phosphate Prodiame Prolame Promestriene Quinestradol Quinestrol Non-steroidal: (R,R)-THC (S,S)-THC 2,8-DHHHC Allenoic acid Alternariol Anethole Anol Benzestrol Bifluranol Biochanin A Bisdehydrodoisynolic acid Carbestrol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Coumestans (e.g., coumestrol, psoralidin) Deoxymiroestrol Dianethole Dianol Diarylpropionitrile Dieldrin Dienestrol Dienestrol acetate Diethylstilbestrol Diethylstilbestrol diacetate Diethylstilbestrol dilaurate Diethylstilbestrol dipalmitate Diethylstilbestrol dipropionate Diethylstilbestrol disulfate Diethylstilbestrol monobenzyl ether Dimestrol (dianisylhexene) Dimethylallenolic acid Doisynoestrol (fenocycline) Doisynolic acid Efavirenz Endosulfan ERB-196 (WAY-202196) Estrobin (DBE) Fenarimol Fenestrel FERb 033 Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate ICI-85966 (Stilbostat) Lavender oil Lignans (e.g., enterodiol, enterolactone) Mestilbol Metalloestrogens (e.g., cadmium) Methallenestril Methestrol Methestrol dipropionate Methiocarb Methoxychlor Miroestrol Nyasol (cis-hinokiresinol) Paroxypropione Pentafluranol Phenestrol Photoanethole Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol)) Quadrosilan SC-4289 SKF-82,958 Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Terfluranol WAY-166818 WAY-200070 Triphenylchlorethylene Triphenylmethylethylene WAY-214156

Mixed (SERMs)	2-Hydroxyestradiol 2-Hydroxyestrone 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordrin Anordriol Arzoxifene Bazedoxifene Brilanestrant Broparestrol Elacestrant Chlorotrianisene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Epitiostanol Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LY-117018 Menerba Mepitiostane Methylepitiostanol Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Phenytoin Pipendoxifene Raloxifene SS1010 Tamoxifen TAS-108 (SR-16234) Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene

Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Cytestrol acetate Fulvestrant (ICI-182780) ICI-164384 Methylpiperidinopyrazole MIBE PHTPP Prochloraz RU-58668 SS1020 TAS-108 (SR-16234) XCT-790 ZK-164015 ZK-191703

GPER

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Equol Estradiol Ethinyl estradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol Tamoxifen Tectoridin Zearalanone Zearalenol Zearalenone Zeranol (zearalanol))

Antagonists	CCL18 Estriol G-15 G-36 MIBE

See also: Androgenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators

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