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E s t e r s o f s t e r o i d a l e s t r o g e n s
T o g g l e E s t e r s o f s t e r o i d a l e s t r o g e n s s u b s e c t i o n
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1 . 1 . 1
M a r k e t e d
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M a r k e t e d
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N e v e r m a r k e t e d
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E t h e r s o f s t e r o i d a l e s t r o g e n s
T o g g l e E t h e r s o f s t e r o i d a l e s t r o g e n s s u b s e c t i o n
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N e v e r m a r k e t e d
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T o g g l e E s t e r s o f n o n s t e r o i d a l e s t r o g e n s s u b s e c t i o n
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Esters of steroidal estrogens [ edit ]
Estradiol esters [ edit ]
Marketed [ edit ]
Many esters of estradiol have been marketed, including the following major esters:[1] [2]
Estradiol acetate (Femring, Femtrace, Menoring)
Estradiol benzoate (Agofollin Depot, Progynon-B; Duogynon, Primosiston, Sistocyclin)
Estradiol cypionate (Depo-Estradiol, Depofemin, Estradep; Cyclofem, Lunelle)
Estradiol dipropionate (Agofollin, Di-Ovocyclin, Progynon-DP; EP Hormone Depot)
Estradiol enantate (Perlutal, Topasel, Unalmes, Yectames)
Estradiol undecylate (Delestrec, Progynon Depot)
Estradiol valerate (Delestrogen, Progynon Depot, Progynova; Gravibinon, Mesigyna, Mesygest)
Polyestradiol phosphate (Estradurin) (an estradiol ester in polymeric form)
And the following less commonly used esters:[1] [2]
Cloxestradiol acetate (Genovul; diacetate ester of cloxestradiol , or estradiol 17β-chloral hemiacetal ether)
Estradiol benzoate butyrate (Redimen, Soluna, Unijab, Unimens)
Estradiol butyrylacetate (Follikoside)
Estradiol dibutyrate (Triormon Depositum)
Estradiol dienantate (Climacteron, Lactimex, Lactostat)
Estradiol diundecylate (Estrolent; Trioestrine Retard)
Estradiol diundecylenate (Etrosteron)
Estradiol furoate (Di-Folliculine)
Estradiol hemisuccinate (Eutocol; Hosterona)
Estradiol hemihydrate (Estrofem)
Estradiol hexahydrobenzoate (Benzo-Ginoestril A.P., BenzoGynoestryl Retard, Ginestryl-15-Depot, Menodin, Tardoginestryl)
Estradiol palmitate (Esmopal)
Estradiol phenylpropionate (Dimenformon Prolongatum; Estandron Prolongatum, Lynandron Prolongatum, Mixogen)
Estradiol pivalate (Estrotate; Estrotate with Progesterone)
Estradiol propionate (estradiol 17β-propionate) (Acrofollin, Akrofollin, Follhormon)
Estradiol propoxyphenylpropionate (Durovex)
Estradiol stearate (Depofollan)
Estradiol sulfate (a minor constituent of conjugated estrogens (Premarin))
The following nitrogen mustard ester of estradiol is a cytostatic antineoplastic agent and has been marketed:[1] [2]
Never marketed [ edit ]
A number of other estradiol esters which have not been marketed include:[2]
The following cytostatic antineoplastic nitrogen mustard esters of estradiol have not been marketed:[2]
Estrone esters [ edit ]
Marketed [ edit ]
Esters of estrone that have been marketed include:[1] [2]
Never marketed [ edit ]
Other estrone esters which are notable but have not been marketed include:
Estriol esters [ edit ]
Marketed [ edit ]
Esters of estriol that have been marketed include:[1] [2]
Never marketed [ edit ]
The following ester of estriol was never marketed:
Ethinylestradiol esters [ edit ]
Marketed [ edit ]
The following esters of ethinylestradiol exist and have been marketed:[1] [2]
Never marketed [ edit ]
Esters of other steroidal estrogens [ edit ]
Marketed [ edit ]
The following esters of other estrogens exist and have been marketed:[1]
Ethers of steroidal estrogens [ edit ]
Marketed [ edit ]
A number of estrogen ethers also exist and have been marketed, including:[22] [1]
Clomestrone (Arterolo, Atheran, Colesterel, Iposclerone, Liprotene, Persclerol) – the 3-methyl ether of 16α-chloroestrone
Cloxestradiol acetate (Genovul) – the O ,O -diacetate ester of cloxestradiol (estradiol 17β-chloral hemiacetal ether)
Mestranol (Devocin, Ovastol, Tranel) (component of Enovid, Enavid, Ortho-Novin, Femigen, Norbiogest) – the 3-methyl ether of ethinylestradiol
Moxestrol (Surestryl) – the 11β-methoxy derivative of ethinylestradiol (and hence the 11β-methyl ether of the 11β-hydroxyl derivative of ethinylestradiol)
Nilestriol (Wei Ni An) – the 3-cyclopentyl ether of ethinylestriol
Promestriene (Colpotrofin, Colpotrophine, Delipoderm) – the 3-propyl and 17β-methyl diether of estradiol
Quinestradol (Colpovis, Colpovister, Pentovis) – the 3-cyclopentyl ether of estriol
Quinestrol (Agalacto-Quilea, Basaquines, Eston, Estrovis, Estrovister, Plestrovis, Qui-lea) – the 3-cyclopentyl ether of ethinylestradiol
Never marketed [ edit ]
A few other estrogen ethers which are notable but have not been marketed include:[22]
Esters of nonsteroidal estrogens [ edit ]
Diethylstilbestrol esters [ edit ]
Marketed [ edit ]
Major esters of diethylstilbestrol include:
Diethylstilbestrol dipropionate (Agostilben, Biokeral, Clinestrol, Cyclen, Estilbin, Estril, Neobenzoestrol, Orestol, Oroestrol, Ostregenin, Prostilbene, Stilbestriol DP, Stilboestrolum Dipropionicum, Stilboestrol, Synestrin, Willestrol)
Fosfestrol (diethylstilbestrol diphosphate) (Honvan, Difostilben, Fosfostilben, Fostrolin, Stilbol, Stilphostrol, Vagestrol)
Less commonly used esters of diethylstilbestrol include:
Never marketed [ edit ]
As well as the following nitrogen mustard ester:
ICI-85966 (Stilbostat; diethylstilbestrol bis(di(2-chloroethyl)carbamate))
Hexestrol esters [ edit ]
Marketed [ edit ]
Never marketed [ edit ]
The following nitrogen mustard ester of hexestrol was never marketed:
Phenestrol (fenestrol; hexestrol bis[4-[bis(2-chloroethyl)amino]phenylacetate)
Esters of other nonsteroidal estrogens [ edit ]
Marketed [ edit ]
Ethers of nonsteroidal estrogens [ edit ]
Diethylstilbestrol [ edit ]
Marketed [ edit ]
Diethylstilbestrol monobenzyl ether (benzelstilbestrol) (Monozol, Hypantin, Pituitrope)
Dimestrol (dianisylhexene, diethylstilbestrol dimethyl ether, dimethoxydiethylstilbestrol) (Depot-Ostromon, Synthila)
Mestilbol (diethylstilbestrol monomethyl ether) (Monomestro or Monomestrol)
See also [ edit ]
References [ edit ]
^ Ferin, J. (1952). "Relative duration of action of natural and synthetic estrogens administered parenterally in women with estrogen deficiency". The Journal of Clinical Endocrinology & Metabolism . 12 (1 ): 28–35. doi :10.1210/jcem-12-1-28 . ISSN 0021-972X . PMID 14907837 .
^ "R&D Research" . Archived from the original on 2017-09-29. Retrieved 2018-06-25 .
^ Elger W, Wyrwa R, Ahmed G, Meece F, Nair HB, Santhamma B, Killeen Z, Schneider B, Meister R, Schubert H, Nickisch K (January 2017). "Estradiol prodrugs (EP ) for efficient oral estrogen treatment and abolished effects on estrogen modulated liver functions". J. Steroid Biochem. Mol. Biol . 165 (Pt B): 305–311. doi :10.1016/j.jsbmb.2016.07.008 . PMID 27449818 . S2CID 26650319 .
^ Ahmed G, Elger W, Meece F, Nair HB, Schneider B, Wyrwa R, Nickisch K (October 2017). "A prodrug design for improved oral absorption and reduced hepatic interaction". Bioorg. Med. Chem . 25 (20 ): 5569–5575. doi :10.1016/j.bmc.2017.08.027 . PMID 28886996 .
^ Nickisch, K., Santhamma, B., Ahmed, G., Meece, F., Elger, W., Wyrwa, R., & Nair, H. (2017). U.S. Patent No. 9,745,338. Washington, DC: U.S. Patent and Trademark Office. https://patents.google.com/patent/US9745338B2/en
^ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy . World Health Organization. pp. 388–. ISBN 978-92-832-1291-1 .
^ Vizzone, A.; Murari, G. (November 1966). "[Estradiol esters (3-monobenzoate and 3-benzoate-17-beta-acetate) in the therapy of the surgical menopause syndrome. Experimental and clinical results]". Quaderni di Clinica Ostetrica e Ginecologica . 21 (11 ): 779–790. PMID 5999221 .
^ a b c Hussain MA, Aungst BJ, Shefter E (January 1988). "Prodrugs for improved oral beta-estradiol bioavailability". Pharm. Res . 5 (1 ): 44–7. doi :10.1023/A:1015863412137 . PMID 3244608 . S2CID 7308414 .
^ a b c Lokind, Kenneth B.; Lorenzen, Finn Hjort; Bundgaard, Hans (1991). "Oral bioavailability of 17β-estradiol and various ester prodrugs in the rat". International Journal of Pharmaceutics . 76 (1–2): 177–182. doi :10.1016/0378-5173(91 )90356-S . ISSN 0378-5173 .
^ a b Falconi G, Galletti F, Celasco G, Gardi R (November 1972). "Oral long-lasting estrogenic activity of estradiol 3-benzoate 17-cyclooctenyl ether". Steroids . 20 (5 ): 627–38. doi :10.1016/0039-128X(72 )90020-7 . PMID 4654978 .
^ Galletti F, Gardi R (April 1974). "Effect of two orally active estradiol derivatives on sulfobromphthalein retention in rats". Pharmacol Res Commun . 6 (2 ): 135–45. doi :10.1016/s0031-6989(74 )80021-4 . PMID 4438394 .
^ Ralph I. Dorfman (5 December 2016). Steroidal Activity in Experimental Animals and Man . Elsevier Science. pp. 36–. ISBN 978-1-4832-7299-3 .
^ Janocko, Laura; Larner, Janice M.; Hochberg, Richard B. (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 . ISSN 0013-7227 . PMID 6705734 .
^ Dahlgren E, Crona N, Janson PO, Samsioe G (1985). "Oral replacement with estradiol-cyclooctyl acetate: a new estradiol analogue. Effects on serum lipids, proteins, gonadotrophins, estrogens and uterine endometrial morphology". Gynecol. Obstet. Invest . 20 (2 ): 84–90. doi :10.1159/000298978 . PMID 3932144 .
^ Luisi M, Kicovic PM, Alicicco E, Franchi F (1978). "Effects of estradiol decanoate in ovariectomized women". J. Endocrinol. Invest . 1 (2 ): 101–6. doi :10.1007/BF03350355 . PMID 755846 . S2CID 38187367 .
^ a b Gleason CH, Parker JM (1959). "The duration of activity of the benziloyl hydrazones of testosterone-17-heptanoate, estrone-3-heptanoate and 17α-hydroxy-progesterone-17-heptanoate". Endocrinology . 65 (3 ): 508–511. doi :10.1210/endo-65-3-508 . ISSN 0013-7227 . PMID 13828402 .
^ George W.A Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties . Taylor & Francis. pp. 1406–. ISBN 978-1-351-78989-9 .
^ a b Elger W, Palme HJ, Schwarz S (April 1998). "Novel oestrogen sulfamates: a new approach to oral hormone therapy". Expert Opin Investig Drugs . 7 (4 ): 575–89. doi :10.1517/13543784.7.4.575 . PMID 15991994 .
^ Elger W, Schwarz S, Hedden A, Reddersen G, Schneider B (December 1995). "Sulfamates of various estrogens are prodrugs with increased systemic and reduced hepatic estrogenicity at oral application". J. Steroid Biochem. Mol. Biol . 55 (3–4): 395–403. doi :10.1016/0960-0760(95 )00214-6 . PMID 8541236 . S2CID 31312 .
^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. ISBN 978-1-4757-2085-3 .
^ Patel JU, Prankerd RJ, Sloan KB (October 1994). "A prodrug approach to increasing the oral potency of a phenolic drug. 1. Synthesis, characterization, and stability of an O-(imidomethyl) derivative of 17 beta-estradiol". J Pharm Sci . 83 (10 ): 1477–81. doi :10.1002/jps.2600831022 . PMID 7884673 .
^ Patel J, Katovich MJ, Sloan KB, Curry SH, Prankerd RJ (February 1995). "A prodrug approach to increasing the oral potency of a phenolic drug. Part 2. Pharmacodynamics and preliminary bioavailability of an orally administered O-(imidomethyl) derivative of 17 beta-estradiol". J Pharm Sci . 84 (2 ): 174–8. doi :10.1002/jps.2600840210 . PMID 7738796 .
^ a b Thomas L. Lemke; David A. Williams (24 January 2012). Foye's Principles of Medicinal Chemistry . Lippincott Williams & Wilkins. pp. 1395–. ISBN 978-1-60913-345-0 .
t
e
Estrogens
ER Tooltip 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
Progonadotropins
Antiestrogens
ER Tooltip Estrogen receptor antagonists (incl. SERMs Tooltip selective estrogen receptor modulators /SERDs Tooltip selective estrogen receptor downregulators )
Aromatase inhibitors
Antigonadotropins
Androgens /anabolic steroids (e.g., testosterone , testosterone esters , nandrolone esters , oxandrolone , fluoxymesterone )
D 2 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
Clinical trials :
See also
Estrogen receptor modulators
Androgens and antiandrogens
Progestogens and antiprogestogens
List of estrogens
t
e
ER Tooltip 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 and esters , methyltestosterone , 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
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
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
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 (SERMs Tooltip Selective estrogen receptor modulators )
Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=List_of_estrogen_esters&oldid=1188162656 "
C a t e g o r i e s :
● E s t r o g e n e s t e r s
● E s t r o g e n s
● S e x h o r m o n e e s t e r s a n d c o n j u g a t e s
H i d d e n c a t e g o r i e s :
● A r t i c l e s w i t h s h o r t d e s c r i p t i o n
● S h o r t d e s c r i p t i o n i s d i f f e r e n t f r o m W i k i d a t a
● T h i s p a g e w a s l a s t e d i t e d o n 3 D e c e m b e r 2 0 2 3 , a t 1 8 : 4 3 ( U T C ) .
● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n .
● P r i v a c y p o l i c y
● A b o u t W i k i p e d i a
● D i s c l a i m e r s
● C o n t a c t W i k i p e d i a
● C o d e o f C o n d u c t
● D e v e l o p e r s
● S t a t i s t i c s
● C o o k i e s t a t e m e n t
● M o b i l e v i e w