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List of estrogen esters

From Wikipedia, the free encyclopedia

Estradiol, the base estrogen of most estrogen esters.

This is alist ofestrogen esters, oresterprodrugs ofestrogens. It includes esters, as well asethers, ofsteroidalestrogens likeestradiol,estrone, andestriol and ofnonsteroidal estrogens like thestilbestrolsdiethylstilbestrol andhexestrol.

Esters of steroidal estrogens

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Estradiol esters

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Marketed

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Many esters of estradiol have been marketed, including the following major esters:[1][2]

And the following less commonly used esters:[1][2]

The followingnitrogen mustard ester of estradiol is acytostatic antineoplastic agent and has been marketed:[1][2]

Never marketed

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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

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Marketed

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Esters of estrone that have been marketed include:[1][2]

Never marketed

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Other estrone esters which are notable but have not been marketed include:

Estriol esters

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Marketed

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Esters of estriol that have been marketed include:[1][2]

Never marketed

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The following ester of estriol was never marketed:

Ethinylestradiol esters

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Marketed

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The following esters ofethinylestradiol exist and have been marketed:[1][2]

Never marketed

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Esters of other steroidal estrogens

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Marketed

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The following esters of other estrogens exist and have been marketed:[1]

Ethers of steroidal estrogens

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Marketed

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A number ofestrogenethers 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) – theO,O-diacetate ester ofcloxestradiol (estradiol 17β-chloral hemiacetal ether)
  • Mestranol (Devocin, Ovastol, Tranel) (component of Enovid, Enavid, Ortho-Novin, Femigen, Norbiogest) – the 3-methyl ether ofethinylestradiol
  • Moxestrol (Surestryl) – the 11β-methoxy derivative ofethinylestradiol (and hence the 11β-methyl ether of the 11β-hydroxyl derivative of ethinylestradiol)
  • Nilestriol (Wei Ni An) – the 3-cyclopentyl ether ofethinylestriol
  • Promestriene (Colpotrofin, Colpotrophine, Delipoderm) – the 3-propyl and 17β-methyl diether ofestradiol
  • Quinestradol (Colpovis, Colpovister, Pentovis) – the 3-cyclopentyl ether ofestriol
  • Quinestrol (Agalacto-Quilea, Basaquines, Eston, Estrovis, Estrovister, Plestrovis, Qui-lea) – the 3-cyclopentyl ether ofethinylestradiol

Never marketed

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A few other estrogen ethers which are notable but have not been marketed include:[22]

Esters of nonsteroidal estrogens

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Diethylstilbestrol esters

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Marketed

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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

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As well as the following nitrogen mustard ester:

  • ICI-85966 (Stilbostat; diethylstilbestrol bis(di(2-chloroethyl)carbamate))

Hexestrol esters

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Marketed

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Never marketed

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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

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Marketed

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Ethers of nonsteroidal estrogens

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Diethylstilbestrol

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Marketed

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  • 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

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References

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  1. ^abcdefghIndexNominum2000. Taylor & Francis US. 2000. p. 404.ISBN 978-3-88763-075-1. Retrieved29 May 2012.
  2. ^abcdefghA. D. Roberts (1991).Dictionary of Steroids: Chemical Data, Structures, and Bibliographies. CRC Press. p. 415.ISBN 978-0-412-27060-4. Retrieved20 May 2012.
  3. ^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.
  4. ^"R&D Research". Archived fromthe original on 2017-09-29. Retrieved2018-06-25.
  5. ^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.
  6. ^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.
  7. ^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
  8. ^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.
  9. ^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.
  10. ^abcHussain 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.
  11. ^abcLokind, 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.
  12. ^abFalconi 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.
  13. ^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.
  14. ^Ralph I. Dorfman (5 December 2016).Steroidal Activity in Experimental Animals and Man. Elsevier Science. pp. 36–.ISBN 978-1-4832-7299-3.
  15. ^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.
  16. ^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.
  17. ^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.
  18. ^abGleason 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.
  19. ^George W.A Milne (8 May 2018).Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1406–.ISBN 978-1-351-78989-9.
  20. ^abElger 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.
  21. ^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.
  22. ^abJ. Elks (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer.ISBN 978-1-4757-2085-3.
  23. ^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.
  24. ^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.
  25. ^abThomas 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.
Salts and covalent derivatives of theestradiol ion
HOE2OH
He
LiBeBvariousNCOE2OHvariousFNe
NaOE2OHMgAlSiHOE2O4PH2
H2PO4E2O4PH2?
(OE2O3PH)n		HSO4E2OH
HSO4E2O4SH		ClE2OH
ClE2Cl?		Ar
KOE2OH?CaScTiVCrMnO4E2OHFeCoNiCuZnGaGeAsHSeO3E2OH
HSeO4E2OH		BrKr
RbOE2OH?SrYZrNbHMoO4E2OHTcRuRhPdAgCdInSnSbTeIXe
CsBa*LuHfTaWReOsIrPtAuHgTlPbBiPoAtRn
FrRa**LrRfDbSgBhHsMtDsRgCnNhFlMcLvTsOg
 
*LaCePrNdPmSmEuGdTbDyHoErTmYb
**AcThPaUNpPuAmCmBkCfEsFmMdNo
Topics
Esters
Related
Estrogens
ERTooltip Estrogen receptor agonists
Progonadotropins
Antiestrogens
ERTooltip Estrogen receptor antagonists
(incl.SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)
Aromatase inhibitors
Antigonadotropins
Others
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
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