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List of estrogen esters#Estradiol esters

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File:Estradiol.svg, the base estrogen of most estrogen esters.]]

This is a list of estrogen esters, or ester prodrugs of estrogens. It includes esters, as well as ethers, of steroidal estrogens like estradiol, estrone, and estriol and of nonsteroidal estrogens like the stilbestrols diethylstilbestrol and hexestrol.

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Esters of steroidal estrogens

=Estradiol esters=

==Marketed==

Many esters of estradiol have been marketed, including the following major esters:{{cite book | title = IndexNominum2000 | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA404 | access-date = 29 May 2012 | year = 2000 | publisher = Taylor & Francis US | isbn = 978-3-88763-075-1 | page = 404}}{{cite book | author = A. D. Roberts | title = Dictionary of Steroids: Chemical Data, Structures, and Bibliographies | url = https://books.google.com/books?id=qw5X0NK1A90C&pg=PA415 | access-date = 20 May 2012 | year = 1991 | publisher = CRC Press | isbn = 978-0-412-27060-4 | page = 415}}

And the following less commonly used esters:

The following nitrogen mustard ester of estradiol is a cytostatic antineoplastic agent and has been marketed:

==Never marketed==

A number of other estradiol esters which have not been marketed include:

  • Estradiol 3-furoate{{cite journal|last1=Ferin|first1=J.|title=Relative duration of action of natural and synthetic estrogens administered parenterally in women with estrogen deficiency|journal=The Journal of Clinical Endocrinology & Metabolism|volume=12|issue=1|year=1952|pages=28–35|issn=0021-972X|doi=10.1210/jcem-12-1-28|pmid=14907837}}
  • Estradiol 3-propionate (not to be confused with estradiol monopropionate (estradiol 17β-propionate))
  • Estradiol 17β-(1-(4-(aminosulfonyl)benzoyl)-L-proline) (EC508){{Cite web | url=http://www.evestra.com/index-Dateien/Page1242.htm | title=R&D Research | access-date=2018-06-25 | archive-date=2017-09-29 | archive-url=https://web.archive.org/web/20170929164030/http://www.evestra.com/index-Dateien/Page1242.htm | url-status=dead }}{{cite journal | vauthors = Elger W, Wyrwa R, Ahmed G, Meece F, Nair HB, Santhamma B, Killeen Z, Schneider B, Meister R, Schubert H, Nickisch K | title = Estradiol prodrugs (EP) for efficient oral estrogen treatment and abolished effects on estrogen modulated liver functions | journal = J. Steroid Biochem. Mol. Biol. | volume = 165 | issue = Pt B | pages = 305–311 | date = January 2017 | pmid = 27449818 | doi = 10.1016/j.jsbmb.2016.07.008 | s2cid = 26650319 }}{{cite journal | vauthors = Ahmed G, Elger W, Meece F, Nair HB, Schneider B, Wyrwa R, Nickisch K | title = A prodrug design for improved oral absorption and reduced hepatic interaction | journal = Bioorg. Med. Chem. | volume = 25 | issue = 20 | pages = 5569–5575 | date = October 2017 | pmid = 28886996 | doi = 10.1016/j.bmc.2017.08.027 }}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
  • Estradiol acetate benzoate{{cite book|author1=IARC Working Group on the Evaluation of Carcinogenic Risks to Humans|author2=World Health Organization|author3=International Agency for Research on Cancer|title=Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy|url=https://books.google.com/books?id=aGDU5xibtNgC&pg=PA388|year=2007|publisher=World Health Organization|isbn=978-92-832-1291-1|pages=388–}}{{cite journal |last1=Vizzone |first1=A. |last2=Murari |first2=G. |title=[Estradiol esters (3-monobenzoate and 3-benzoate-17-beta-acetate) in the therapy of the surgical menopause syndrome. Experimental and clinical results] |journal=Quaderni di Clinica Ostetrica e Ginecologica |date=November 1966 |volume=21 |issue=11 |pages=779–790 |pmid=5999221 }}
  • Estradiol 17β-acetate
  • Estradiol 17β-benzoate
  • Estradiol acetylsalicylate (estradiol 3-acetylsalicylate){{cite journal | vauthors = Hussain MA, Aungst BJ, Shefter E | title = Prodrugs for improved oral beta-estradiol bioavailability | journal = Pharm. Res. | volume = 5 | issue = 1 | pages = 44–7 | date = January 1988 | pmid = 3244608 | doi = 10.1023/A:1015863412137 | s2cid = 7308414 }}{{cite journal|last1=Lokind|first1=Kenneth B.|last2=Lorenzen|first2=Finn Hjort|last3=Bundgaard|first3=Hans|title=Oral bioavailability of 17β-estradiol and various ester prodrugs in the rat|journal=International Journal of Pharmaceutics|volume=76|issue=1–2|year=1991|pages=177–182|issn=0378-5173|doi=10.1016/0378-5173(91)90356-S}}
  • Estradiol anthranilate (estradiol 3-anthranilate)
  • Estradiol arachidonate
  • Estradiol benzoate cyclooctenyl ether (estradiol 3-benzoate 17β-cyclooctenyl ether; EBCO){{cite journal | vauthors = Falconi G, Galletti F, Celasco G, Gardi R | title = Oral long-lasting estrogenic activity of estradiol 3-benzoate 17-cyclooctenyl ether | journal = Steroids | volume = 20 | issue = 5 | pages = 627–38 | date = November 1972 | pmid = 4654978 | doi = 10.1016/0039-128X(72)90020-7 }}{{cite journal | vauthors = Galletti F, Gardi R | title = Effect of two orally active estradiol derivatives on sulfobromphthalein retention in rats | journal = Pharmacol Res Commun | volume = 6 | issue = 2 | pages = 135–45 | date = April 1974 | pmid = 4438394 | doi = 10.1016/s0031-6989(74)80021-4 }}
  • Estradiol caprylate (estradiol octanoate){{cite book|author=Ralph I. Dorfman|title=Steroidal Activity in Experimental Animals and Man|url=https://books.google.com/books?id=BbLfBAAAQBAJ&pg=PA36|date=5 December 2016|publisher=Elsevier Science|isbn=978-1-4832-7299-3|pages=36–}}{{cite journal|last1=Janocko|first1=Laura|last2=Larner|first2=Janice M.|last3=Hochberg|first3=Richard B.|title=The Interaction of C-17 Esters of Estradiol with the Estrogen Receptor*|journal=Endocrinology|volume=114|issue=4|year=1984|pages=1180–1186|issn=0013-7227|doi=10.1210/endo-114-4-1180|pmid=6705734}}
  • Estradiol cyclooctyl acetate (E2CoA){{cite journal | vauthors = Dahlgren E, Crona N, Janson PO, Samsioe G | title = Oral replacement with estradiol-cyclooctyl acetate: a new estradiol analogue. Effects on serum lipids, proteins, gonadotrophins, estrogens and uterine endometrial morphology | journal = Gynecol. Obstet. Invest. | volume = 20 | issue = 2 | pages = 84–90 | year = 1985 | pmid = 3932144 | doi = 10.1159/000298978}}
  • Estradiol decanoate (estradiol 17β-decanoate){{cite journal | vauthors = Luisi M, Kicovic PM, Alicicco E, Franchi F | title = Effects of estradiol decanoate in ovariectomized women | journal = J. Endocrinol. Invest. | volume = 1 | issue = 2 | pages = 101–6 | year = 1978 | pmid = 755846 | doi = 10.1007/BF03350355 | s2cid = 38187367 }}
  • Estradiol diacetate
  • Estradiol dibenzoate
  • Estradiol dicypionate
  • Estradiol dioleate
  • Estradiol dipalmitate
  • Estradiol distearate
  • Estradiol disulfate
  • Estradiol glucuronide
  • Estradiol sulfate glucuronide
  • Estradiol linoleate
  • Estradiol oleate
  • Estradiol phosphate
  • Estradiol salicylate (estradiol 3-salicylate)
  • Estradiol sulfamate (E2MATE; J995, PGL-2, PGL-2001, ZK-190628; estradiol-3-O-sulfamate)
  • Estradiol undecylenate (SH-368)
  • Estrapronicate (estradiol 3-propionate 17β-nicotinate; Trophobolene, Trophoboline)
  • Orestrate (estradiol 3-propionate 17β-(1-cyclohexenyl) ether)

The following cytostatic antineoplastic nitrogen mustard esters of estradiol have not been marketed:

  • Alestramustine (estradiol 3-(bis(2-chloroethyl)carbamate), 17-ester with L-alanine)
  • Atrimustine (KM-2210; bestrabucil, busramustine)
  • Estradiol mustard (NSC-112259; chlorphenacyl estradiol diester)
  • Estramustine (Leo 275; Ro 21-8837)
  • Estromustine (Leo 271 f; estrone 17β-3-N-bis(2-chloroethyl)carbamate, estrone–cytostatic complex)

=Estrone esters=

==Marketed==

Esters of estrone that have been marketed include:

==Never marketed==

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

  • Estrone benzoate
  • Estrone cyanate
  • Estrone enanthate{{cite journal|vauthors=Gleason CH, Parker JM|title=The duration of activity of the benziloyl hydrazones of testosterone-17-heptanoate, estrone-3-heptanoate and 17α-hydroxy-progesterone-17-heptanoate|journal=Endocrinology|volume=65|issue=3|year=1959|pages=508–511|issn=0013-7227|pmid=13828402|doi=10.1210/endo-65-3-508}}
  • Estrone enanthate benzilic acid hydrazone
  • Estrone glucuronide
  • Estrone phosphate
  • Estrone propionate{{cite book|author=George W.A Milne|title=Drugs: Synonyms and Properties: Synonyms and Properties|url=https://books.google.com/books?id=xUlaDwAAQBAJ&pg=PT1406|date=8 May 2018|publisher=Taylor & Francis|isbn=978-1-351-78989-9|pages=1406–}}
  • Estrone sulfamate (EMATE; J994; estrone-3-O-sulfamate)
  • Estrone oleate

=Estriol esters=

==Marketed==

Esters of estriol that have been marketed include:

==Never marketed==

The following ester of estriol was never marketed:

=Ethinylestradiol esters=

==Marketed==

The following esters of ethinylestradiol exist and have been marketed:

==Never marketed==

  • Ethinylestradiol benzoate – the 3-benzoate ester of ethinylestradiol
  • Ethinylestradiol N,N-diethylsulfamate (J271) – the 3-(N,N-diethyl)sulfamate ester of ethinylestradiol{{cite journal | vauthors = Elger W, Palme HJ, Schwarz S | title = Novel oestrogen sulfamates: a new approach to oral hormone therapy | journal = Expert Opin Investig Drugs | volume = 7 | issue = 4 | pages = 575–89 | date = April 1998 | pmid = 15991994 | doi = 10.1517/13543784.7.4.575 }}
  • Ethinylestradiol pyrrolidinosulfonate (J272) – the 3-pyrrolidinosulfonate ester of ethinylestradiol
  • Ethinylestradiol sulfamate (J1028) – the 3-sulfamate ester of ethinylestradiol{{cite journal | vauthors = Elger W, Schwarz S, Hedden A, Reddersen G, Schneider B | title = Sulfamates of various estrogens are prodrugs with increased systemic and reduced hepatic estrogenicity at oral application | journal = J. Steroid Biochem. Mol. Biol. | volume = 55 | issue = 3–4 | pages = 395–403 | date = December 1995 | pmid = 8541236 | doi = 10.1016/0960-0760(95)00214-6 | s2cid = 31312 }}
  • Ethinylestradiol sulfate

=Esters of other steroidal estrogens=

==Marketed==

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

Ethers of steroidal estrogens

=Marketed=

A number of estrogen ethers also exist and have been marketed, including:{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PR2|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3}}

  • 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=

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

  • Cloxestradiol – the 17β-chloral hemiacetal ether of estradiol
  • Estradiol benzoate cyclooctenyl ether – the 17β-cyclooctenyl ether of estradiol 3-benzoate
  • Estradiol 3-saccharinylmethyl ether – the 3-(saccharinylmethyl) ether of estradiol{{cite journal | vauthors = Patel JU, Prankerd RJ, Sloan KB | title = 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 | journal = J Pharm Sci | volume = 83 | issue = 10 | pages = 1477–81 | date = October 1994 | pmid = 7884673 | doi = 10.1002/jps.2600831022 }}{{cite journal | vauthors = Patel J, Katovich MJ, Sloan KB, Curry SH, Prankerd RJ | title = 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 | journal = J Pharm Sci | volume = 84 | issue = 2 | pages = 174–8 | date = February 1995 | pmid = 7738796 | doi = 10.1002/jps.2600840210 }}
  • Estradiol 3-tetrahydropyranyl ether – the 3-(tetrahydropyran-2-yl) ether of estradiol{{cite book|author1=Thomas L. Lemke|author2=David A. Williams|title=Foye's Principles of Medicinal Chemistry|url=https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1395|date=24 January 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-60913-345-0|pages=1395–}}
  • Estradiol 17β-tetrahydropyranyl ether – the 17β-(tetrahydropyran-2-yl) ether of estradiol
  • Estrone methyl ether – the 3-methyl ether of estrone
  • Mytatrienediol – the 3-methyl ether of 16α-methyl-16β-epiestriol
  • Orestrate – the 17β-(1-cyclohexenyl) ether of estradiol 3-propionate

Esters of nonsteroidal estrogens

=Diethylstilbestrol esters=

==Marketed==

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==

As well as the following nitrogen mustard ester:

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

=Hexestrol esters=

==Marketed==

==Never marketed==

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=

==Marketed==

Ethers of nonsteroidal estrogens

=Diethylstilbestrol=

==Marketed==

  • 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

References

{{Reflist}}

{{Estradiol salts}}

{{Estradiol}}

{{Estrogens and antiestrogens}}

{{Estrogen receptor modulators}}

Category:Estrogen esters

Category:Estrogens

Category:Sex hormone esters and conjugates