List of estrogen esters

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Estradiol, the base estrogen of most estrogen esters. Estradiol.svg
Estradiol, 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.

Contents

Esters of steroidal estrogens

Estradiol esters

Marketed

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

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

The following nitrogen mustard ester of estradiol is a cytostatic antineoplastic agent and has been marketed: [1] [2]

Never marketed

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]

  • 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: [1] [2]

Never marketed

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

Estriol esters

Marketed

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

Never marketed

The following ester of estriol was never marketed:

Ethinylestradiol esters

Marketed

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

Never marketed

Esters of other steroidal estrogens

Marketed

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

Ethers of steroidal estrogens

Marketed

A number of estrogen ethers also exist and have been marketed, including: [22] [1]

Never marketed

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

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

  1. 1 2 3 4 5 6 7 8 IndexNominum2000. Taylor & Francis US. 2000. p. 404. ISBN   978-3-88763-075-1 . Retrieved 29 May 2012.
  2. 1 2 3 4 5 6 7 8 A. D. Roberts (1991). Dictionary of Steroids: Chemical Data, Structures, and Bibliographies. CRC Press. p. 415. ISBN   978-0-412-27060-4 . Retrieved 20 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 from the original on 2017-09-29. Retrieved 2018-06-25.
  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. 1 2 3 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.
  11. 1 2 3 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.
  12. 1 2 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.
  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. 1 2 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.
  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. 1 2 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.
  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. 1 2 J. 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. 1 2 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.
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