An estrogen ester is an ester of an endogenous, steroidal estrogen, generally estradiol but also estrone or estriol.[1] Esterification renders these drugs into metabolically-resistant prohormones of their respective parent estrogen, improving oral bioavailability, increasing lipophilicity, and extending half-life (which necessitates less frequent administration).[2] In addition, with intramuscular injection, they are absorbed more slowly into the body, further improving half-life.[1]
Estrogen esters are used in hormone replacement therapy and as hormonal contraceptives, among other indications.
The first estrogen ester to be marketed was estradiol benzoate in 1936,[3][4] which was quickly followed by many more.
List of estrogen esters
Many esters of estradiol have been marketed, including the following:[5][6]
- Cloxestradiol acetate (Genovul)
- Estradiol acetate (Femring, Femtrace, Menoring)
- Estradiol benzoate (Agofollin, Diffolisterol, Progynon-B)
- Estradiol butyrylacetate (Follikoside)
- Estradiol cypionate (Depo-Estradiol, Depofemin, Estradep)
- Estradiol dipropionate (Agofollin, Diovocyclin, Progynon-DP)
- Estradiol diundecylate (Estrolent, Etrosteron, Theramex)
- Estradiol enanthate (Anafertin, Deladroxate, Perlutan, Topasel, all in combination with dihydroxyprogesterone acetophenide)
- Estradiol furoate (Di-folliculine)
- Estradiol hemihydrate
- Estradiol hemisuccinate (Eutocol)
- Estradiol hexahydrobenzoate (Benzo-Ginoestril, Ginestryl-15-depot, Menodin, Tardoginestryl)
- Estradiol monopropionate (Acrofollin, Akrofollin, Follhormon)
- Estradiol palmitate (Esmopal)
- Estradiol propoxyphenylpropionate (Durovex)
- Estradiol stearate (Depofollan)
- Estradiol undecylate (Delestrec, Depogin, Primogyn Depot, Progynon Depot)
- Estradiol valerate (Altadiol, Climaval, Deladiol, Delestrogen, Estraval, Progynova, Valergen)
- Estramustine (Emcyt, Estracit)
- Trimethyl estradiol acetate (Estrotate)
As well as the following esters of other estrogens:[5][6]
A few other estrogen esters which are notable but have not been marketed include atrimustine (bestrabucil), estrapronicate, orestrate, which are estradiol esters.[6]
See also
References
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Estrogens |
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Antiestrogens |
SERMs / antagonists |
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Aromatase inhibitors |
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Antigonadotropins |
- Androgens/anabolic steroids (e.g., testosterone, nandrolone, oxandrolone)
- GnRH agonists (e.g., leuprorelin)
- GnRH antagonists (e.g., cetrorelix)
- Progestogens (incl. allylestrenol, chlormadinone acetate, cyproterone acetate, delmadinone acetate, dydrogesterone, medroxyprogesterone acetate, megestrol acetate, nomegestrol acetate, norethisterone acetate, progesterone, spironolactone)
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Description |
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Disease |
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Treatment |
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Receptor
(ligands) |
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Agonists
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- (R)-DPN
- (S)-DPN
- (R,R)-THC
- (S,S)-THC
- 2,8-DHHHC
- 3α-Androstanediol
- 3β-Androstanediol
- 3α-Hydroxytibolone
- 3β-Hydroxytibolone
- 7-Oxo-DHEA
- 7α-Hydroxy-DHEA
- 7β-Hydroxyepiandrosterone
- 8β-VE2
- 16α-Hydroxy-DHEA
- 16α-Hydroxyestrone
- 16α-IE2
- 16α-LE2 (Cpd1471)
- Δ4-Androstenedione
- Δ5-Androstenediol
- 17α-Estradiol (alfatradiol)
- 17β-Estradiol (estradiol)
- Alestramustine
- Almestrone
- Anabolic steroids (prodrugs; e.g., testosterone, metandienone (methandrostenolone), others)
- Anethole
- Anol
- Atrimustine
- Benzestrol
- Bifluranol
- Bisdehydrodoisynolic acid
- Cadmium
- Carbestrol
- Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
- Cloxestradiol
- Conjugated equine estrogens (e.g., sodium equilin sulfate, sodium equilenin sulfate)
- Coumestans (e.g., coumestrol, psoralidin)
- DHEA
- DHEA-S
- Deoxymiroestrol
- Dianethole
- Dianol
- Diarylpropionitrile
- Dieldrin
- Dienestrol
- Dienestrol acetate
- Diethylstilbestrol
- Diethylstilbestrol dipropionate
- Diosgenin
- Doisynoestrol (fenocycline)
- Doisynolic acid
- DY-131 (GSK-9089)
- Endosulfan
- Epiestriol
- Epimestrol
- ERB-196 (WAY-202196)
- Esterified estrogens (e.g., estrone sulfate, equilin sulfate, equilenin sulfate)
- Estetrol
- Estradiol benzoate
- Estradiol butyrylacetate
- Estradiol cypionate
- Estradiol dienanthate
- Estradiol dipropionate
- Estradiol diundecylate
- Estradiol diundecylenate
- Estradiol enanthate
- Estradiol furoate
- Estradiol hemihydrate
- Estradiol hemisuccinate
- Estradiol hexahydrobenzoate
- Estradiol monopropionate
- Estradiol palmitate
- Estradiol pivalate
- Estradiol propoxyphenylpropionate
- Estradiol stearate
- Estradiol succinate
- Estradiol undecylate
- Estradiol valerate
- Estramustine
- Estramustine phosphate
- Estrapronicate
- Estrazinol
- Estriol
- Estriol succinate
- Estriol tripropionate
- Estrobin (DBE)
- Estrofurate
- Estromustine
- Estrone
- Estrone acetate
- Estrone cyanate
- Estrone sulfate
- Estrone tetraacetylglucoside
- Estropipate
- Estropronicate
- Etamestrol (eptamestrol)
- Ethinyl estradiol
- Ethinyl estradiol 3-isopropylsulfonate
- Etynodiol diacetate
- 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
- Furostilbestrol
- GSK-4716
- Hexestrol
- Hexestrol diacetate
- Hexestrol dicaprylate
- Hexestrol diphosphate
- Hexestrol dipropionate
- Hydroxyestrone diacetate
- Lavender oil
- Lignans (e.g., enterodiol, enterolactone)
- Mestranol
- Metalloestrogens (e.g., cadmium)
- Methallenestril
- Methestrol
- Methestrol dipropionate
- Methiocarb
- Methylestradiol
- Miroestrol
- Moxestrol
- Nilestriol
- Noretynodrel
- Orestrate
- Paroxypropione
- Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
- Polyestradiol phosphate
- Prinaberel (ERB-041, WAY-202041)
- Propylpyrazoletriol
- Promestriene
- Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranal (zearalanol))
- Quadrosilan
- Quinestradol
- Quinestrol
- SKF-82,958
- Stilbenoids (e.g., resveratrol)
- Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
- WAY-166818
- WAY-200070
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Antagonists
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Enzyme |
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Others |
Precursors
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Indirect
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- Antigonadotropins (e.g., androgens, estrogens, progestogens, prolactin)
- Calcitriol (vitamin D)
- GnRH agonists (e,g, GnRH, leuprorelin)
- GnRH antagonists (e.g., cetrorelix)
- Gonadotropins (e.g., FSH, hCG, LH)
- Kisspeptin
- Plasma proteins (ABP, albumin, SHBG)
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