List of 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.

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 an alkylating antineoplastic agent and has been marketed:[1][2]

Never marketed

A few other estradiol esters which are notable but have not been marketed include:[2]

The following alkylating 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:[14][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

A few other estrogen ethers which are notable but have not been marketed include:[14]

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

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  3. http://www.evestra.com/index-Dateien/Page1242.htm
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  8. 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.
  9. 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.
  10. 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. PMID 3932144.
  11. 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.
  12. 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.
  13. 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.
  14. 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.
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  16. 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.
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