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Estradiol distearate

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Chemical compound

Pharmaceutical compound

Estradiol distearate
Clinical data

Other names	EDS; Estradiol 3,17β-distearate; Estradiol dioctadecanoate; Estra-1,3,5(10)-triene-3,17β-diol 3,17β-dioctadecanoate
Identifiers
IUPAC name [(8R,9S,13S,14S,17S)-13-methyl-3-octadecanoyloxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] octadecanoate
CAS Number	126144-03-4^Y
PubChemCID	53672832
UNII	B8HEM55UGK
Chemical and physical data
Formula	C₅₄H₉₂O₄
Molar mass	805.326 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)OC(=O)CCCCCCCCCCCCCCCCC)C
InChI InChI=1S/C54H92O4/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-52(55)57-46-37-39-47-45(44-46)36-38-49-48(47)42-43-54(3)50(49)40-41-51(54)58-53(56)35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-5-2/h37,39,44,48-51H,4-36,38,40-43H2,1-3H3/t48-,49-,50+,51+,54+/m1/s1 Key:BBBPCTNBNYFUOV-NXCWIAOISA-N

Estradiol distearate (EDS), also known asestradiol dioctadecanoate, is anestrogen and anestrogen ester, which was never marketed.^[1]^[2] It is a long-actingprodrug ofestradiol in the body.^[2]

v
t
e
Structural properties of selected estradiol esters
Estrogen	Structure	Ester(s)				Relative mol. weight	Relative E2 content^b	log P^c
Estrogen	Structure	Position(s)	Moiet(ies)	Type	Length^a	Relative mol. weight	Relative E2 content^b	log P^c
Estradiol		–	–	–	–	1.00	1.00	4.0
Estradiol acetate		C3	Ethanoic acid	Straight-chain fatty acid	2	1.15	0.87	4.2
Estradiol benzoate		C3	Benzoic acid	Aromatic fatty acid	– (~4–5)	1.38	0.72	4.7
Estradiol dipropionate		C3, C17β	Propanoic acid (×2)	Straight-chain fatty acid	3 (×2)	1.41	0.71	4.9
Estradiol valerate		C17β	Pentanoic acid	Straight-chain fatty acid	5	1.31	0.76	5.6–6.3
Estradiol benzoate butyrate		C3, C17β	Benzoic acid,butyric acid	Mixed fatty acid	– (~6, 2)	1.64	0.61	6.3
Estradiol cypionate		C17β	Cyclopentylpropanoic acid	Cyclic fatty acid	– (~6)	1.46	0.69	6.9
Estradiol enanthate		C17β	Heptanoic acid	Straight-chain fatty acid	7	1.41	0.71	6.7–7.3
Estradiol dienanthate		C3, C17β	Heptanoic acid (×2)	Straight-chain fatty acid	7 (×2)	1.82	0.55	8.1–10.4
Estradiol undecylate		C17β	Undecanoic acid	Straight-chain fatty acid	11	1.62	0.62	9.2–9.8
Estradiol stearate		C17β	Octadecanoic acid	Straight-chain fatty acid	18	1.98	0.51	12.2–12.4
Estradiol distearate		C3, C17β	Octadecanoic acid (×2)	Straight-chain fatty acid	18 (×2)	2.96	0.34	20.2
Estradiol sulfate		C3	Sulfuric acid	Water-soluble conjugate	–	1.29	0.77	0.3–3.8
Estradiol glucuronide		C17β	Glucuronic acid	Water-soluble conjugate	–	1.65	0.61	2.1–2.7
Estramustine phosphate^d		C3, C17β	Normustine,phosphoric acid	Water-soluble conjugate	–	1.91	0.52	2.9–5.0
Polyestradiol phosphate^e		C3–C17β	Phosphoric acid	Water-soluble conjugate	–	1.23^f	0.81^f	2.9^g
Footnotes:^a = Length ofester incarbon atoms forstraight-chain fatty acids or approximate length of ester in carbon atoms foraromatic orcyclic fatty acids.^b = Relative estradiol content by weight (i.e., relativeestrogenic exposure).^c = Experimental or predictedoctanol/water partition coefficient (i.e.,lipophilicity/hydrophobicity). Retrieved fromPubChem,ChemSpider, andDrugBank.^d = Also known asestradiol normustine phosphate.^e =Polymer ofestradiol phosphate (~13repeat units).^f = Relative molecular weight or estradiol content per repeat unit.^g = log P of repeat unit (i.e., estradiol phosphate).Sources: See individual articles.

References

[edit]

^Deb S, Wähälä K (October 2010). "Rapid synthesis of long chain fatty acid esters of steroids in ionic liquids with microwave irradiation: expedient one-pot procedure for estradiol monoesters".Steroids.75 (10):740–4.doi:10.1016/j.steroids.2010.03.005.PMID 20347856.S2CID 1695106.
^^a ^bVazquez-Alcantara MA, Menjivar M, Garcia GA, Díaz-Zagoya JC, Garza-Flores J (December 1989). "Long-acting estrogenic responses of estradiol fatty acid esters".Journal of Steroid Biochemistry.33 (6):1111–8.doi:10.1016/0022-4731(89)90417-2.PMID 2515394.

v t e Estradiol
Topics	Estradiol (as a hormone) Estradiol (as a medication) Pharmacodynamics of estradiol Pharmacokinetics of estradiol Estrogen (as a hormone) Estrogen (as a medication) Menopausal hormone therapy Feminizing hormone therapy Estradiol-containing birth control pill Combined injectable birth control High-dose estrogen Hydroxylation of estradiol
Esters	Estradiol acetate Estradiol acetylsalicylate Estradiol anthranilate Estradiol benzoate butyrate Estradiol benzoate cyclooctenyl ether Estradiol benzoate Estradiol butyrylacetate Estradiol cyclooctyl acetate Estradiol cypionate Estradiol decanoate Estradiol diacetate Estradiol dibutyrate Estradiol dienantate Estradiol dipropionate Estradiol distearate Estradiol disulfate Estradiol diundecylate Estradiol diundecylenate Estradiol enantate Estradiol furoate Estradiol glucuronide Estradiol hemisuccinate Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol mustard Estradiol palmitate Estradiol phenylpropionate Estradiol phosphate Estradiol pivalate Estradiol propoxyphenylpropionate Estradiol salicylate Estradiol stearate Estradiol sulfamate Estradiol sulfate Estradiol undecylate Estradiol undecylenate Estradiol valerate Estramustine phosphate (estradiol normustine phosphate) Estrogen ester Polyestradiol phosphate
Related	Estrone Estriol Estetrol Ethinylestradiol Conjugated estrogens Esterified estrogens Estrone sulfate Estropipate (piperazine estrone sulfate)

Estrogens andantiestrogens

Estrogens

ERTooltip Estrogen receptor agonists

Progonadotropins

Antiandrogens (e.g.,bicalutamide)
GnRH agonists (e.g.,GnRH (gonadorelin),leuprorelin)
Gonadotropins (e.g.,FSHTooltip follicle-stimulating hormone,LHTooltip luteinizing hormone)

Antiestrogens

ERTooltip Estrogen receptor antagonists (incl.SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)	Acolbifene^† Anordrin Bazedoxifene Broparestrol Clomifene^# Cyclofenil Enclomifene^† Epitiostanol Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Raloxifene Tamoxifen^# Toremifene Exclusively antagonistic:Elacestrant Fulvestrant Imlunestrant Noncompetitive inhibitors:Trilostane
Aromatase inhibitors	First-generation:Aminoglutethimide Testolactone Second-generation:Fadrozole Formestane Third-generation:Anastrozole Exemestane Letrozole
Antigonadotropins	Androgens/anabolic steroids (e.g.,testosterone,testosterone esters,nandrolone esters,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,elagolix) Progestogens (e.g.,chlormadinone acetate,cyproterone acetate,gestonorone caproate,hydroxyprogesterone caproate,medroxyprogesterone acetate,megestrol acetate)
Others	Mixed mechanism of action:Danazol Gestrinone Androstenedione immunogens:Androvax (androstenedione albumin) Ovandrotone albumin (Fecundin)

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

See also: Estrogen receptor modulators; Androgens and antiandrogens; Progestogens and antiprogestogens; List of estrogens

Estrogen receptor modulators

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 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 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 Anabolic steroids (e.g.,testosterone andesters,methyltestosterone,metandienone (methandrostenolone),nandrolone andesters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Cloxestradiol acetate 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 Estradiol esters Lipoidal estradiol Polyestradiol phosphate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol esters Polyestriol phosphate Estrofurate Estrogenic substances Estromustine Estrone Estrone esters Estrone methyl ether Estropipate Etamestrol (eptamestrol) Ethinylandrostenediol Ethandrostate Ethinylestradiol Ethinylestradiol 3-benzoate Ethinylestradiol sulfonate Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Nonsteroidal:(R,R)-THC (S,S)-THC 2,8-DHHHC β-LGND1 β-LGND2 (GTx-878) AC-186 Allenestrol Allenolic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Butestrol Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol Dienestrol diacetate Diethylstilbestrol Diethylstilbestrol esters Dimestrol (dianisylhexene) Dimethylstilbestrol Doisynoestrol (fenocycline) Doisynolic acid Efavirenz Elacestrant ERB-196 (WAY-202196) Erteberel (SERBA-1, LY-500307) Estrobin (DBE) Fenestrel FERb 033 Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol esters ICI-85966 (Stilbostat) M2613 meso-Butestrol meso-Hexestrol Mestilbol Methallenestril Methestrol Methestrol dipropionate Paroxypropione Pentafluranol Phenestrol Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Quadrosilan SC-3296 SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene (triphenylpropene) WAY-166818 WAY-169916 WAY-200070 WAY-204688 (SIM-688) WAY-214156 Unknown/unsorted:ERB-26 ERA-45 ERB-79 ZK-283197 Xenoestrogens:Anise-related (e.g.,anethole,anol,dianethole,dianol,photoanethole) Chalconoids (e.g.,isoliquiritigenin,phloretin,phlorizin (phloridzin),wedelolactone) Coumestans (e.g.,coumestrol,psoralidin) Flavonoids (incl.7,8-DHF,8-prenylnaringenin,apigenin,baicalein,baicalin,biochanin A,calycosin,catechin,daidzein,daidzin,ECG,EGCG,epicatechin,equol,formononetin,glabrene,glabridin,genistein,genistin,glycitein,kaempferol,liquiritigenin,mirificin,myricetin,naringenin,penduletin,pinocembrin,prunetin,puerarin,quercetin,tectoridin,tectorigenin) Lavender oil Lignans (e.g.,enterodiol,enterolactone,nyasol (cis-hinokiresinol)) Metalloestrogens (e.g.,cadmium) Pesticides (e.g.,alternariol,dieldrin,endosulfan,fenarimol,HPTE,methiocarb,methoxychlor,triclocarban,triclosan) Phytosteroids (e.g.,digitoxin (digitalis),diosgenin,guggulsterone) Phytosterols (e.g.,β-sitosterol,campesterol,stigmasterol) Resorcylic acid lactones (e.g.,zearalanone,α-zearalenol,β-zearalenol,zearalenone,zeranol (α-zearalanol),taleranol (teranol, β-zearalanol)) Steroid-like (e.g.,deoxymiroestrol,miroestrol) Stilbenoids (e.g.,resveratrol,rhaponticin) Synthetic xenoestrogens (e.g.,alkylphenols,bisphenols (e.g.,BPA,BPF,BPS),DDT,parabens,PBBs,PHBA,phthalates,PCBs) Others (e.g.,agnuside,rotundifuran)
Mixed (SERMsTooltip Selective estrogen receptor modulators)	2-Phenylbenzofuran 2-Phenyl-1-benzothiophene 4'-Hydroxynorendoxifen 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordiol Anordrin Arzoxifene Bazedoxifene Brilanestrant Broparestrol Camizestrant Chlorotrianisene Clomifene Clomifenoxide CN-55945-27 Cyclofenil D-15413 Desmethylchlorotrianisene Droloxifene Enclomifene Endoxifen Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW-7604 ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LN-1643 LN-2299 LY-117018 Menerba Miproxifene Miproxifene phosphate MRL-37 Nafoxidine Nitromifene NNC 45-0095 NNC 45-0320 NNC 45-0781 NNC 45-1506 Ormeloxifene Ospemifene Panomifene Pipendoxifene Promensil Raloxifene Rimostil (P-081) Spironolactone SS1010 Tamoxifen TAS-108 (SR-16234) Toremifene Trioxifene TZE-5323 U-11555A U-11634 Y-134 Zindoxifene Zuclomifene
Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Chloroindazole Cytestrol acetate EM-800 (SCH-57050) Epitiostanol ERA-90 ERB-88 Fulvestrant (ICI-182780) Glyceollins (I,II,III,IV) ICI-164384 MDL-101906 Mepitiostane Methylepitiostanol Methylpiperidinopyrazole MIBE Oxabicycloheptene sulfonate Phenytoin PHTPP Prochloraz RU-39411 RU-58668 SS1020 TAS-108 (SR-16234) ZB716 ZK-164015 ZK-191703 Coregulator-binding modulators:ERX-11 Noncompetitive inhibitors:Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT,o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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