List of estrogen esters
This is a list of estrogen esters, including esters (as well as ethers) of steroidal estrogens like estradiol, estrone, and estriol and 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]
- Estradiol acetate (Femring, Femtrace, Menoring)
- Estradiol benzoate (Agofollin, Diffolisterol, Progynon-B)
- Estradiol cypionate (Depo-Estradiol, Depofemin, Estradep)
- Estradiol enanthate (Anafertin, Deladroxate, Perlutan, Topasel, all in combination with algestone acetophenide)
- Estradiol undecylate (Delestrec, Depogin, Primogyn Depot, Progynon Depot, Oestradiol-Retard Theramex)
- Estradiol valerate (Altadiol, Climaval, Deladiol, Delestrogen, Estraval, Progynon Depot, Progynova, Valergen)
- Polyestradiol phosphate (Estradurin) (an estradiol ester in polymeric form)
And the following less commonly used esters:[1][2]
- Estradiol butyrylacetate (Follikoside)
- Estradiol dienanthate (Climacteron, in combination with estradiol benzoate and testosterone esters)
- Estradiol dipropionate (Agofollin, Diovocyclin, Progynon-DP)
- Estradiol diundecylate (Estrolent)
- Estradiol diundecylenate (Etrosteron)
- Estradiol furoate (Di-Folliculine)
- Estradiol hemisuccinate (Eutocol)
- Estradiol hexahydrobenzoate (Benzo-Ginoestril, Ginestryl-15-Depot, Menodin, Tardoginestryl)
- Estradiol monopropionate (estradiol 17β-propionate) (Acrofollin, Akrofollin, Follhormon)
- Estradiol palmitate (Esmopal)
- Estradiol phenylpropionate (Dimenformon Prolongatum, Mixogen, all in combination with estradiol benzoate and/or testosterone esters)
- Estradiol pivalate (Estrotate)
- Estradiol propoxyphenylpropionate (Durovex)
- Estradiol stearate (Depofollan)
- Estradiol sulfate (a minor constituent of Premarin)
The following nitrogen mustard ester of estradiol is an alkylating antineoplastic agent and has been marketed:[1][2]
- Estramustine phosphate (Emcyt, Estracyt)
Never marketed
A few other estradiol esters which are notable but have not been marketed include:[2]
- Estradiol 3-propionate (not to be confused with estradiol monopropionate (estradiol 17β-propionate))
- Estradiol butyrate benzoate (estradiol 3-benzoate 17β-n-butyrate)
- Estradiol cyclooctyl acetate (E2CoA)[3]
- Estradiol decanoate (estradiol 17β-decanoate)[4]
- Estradiol glucuronide
- Estradiol sulfamate (E2MATE; J995, PGL-2, PGL-2001, ZK-190628; estradiol-3-O-sulfamate)
- Estrapronicate (estradiol 3-propionate 17β-nicotinate)
- Orestrate (estradiol 3-propionate 17β-(1-cyclohexenyl) ether)
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]
- Estrone acetate (Hovigal)
- Estrone sulfate (as the primary component of Premarin)
- Estropipate (Ogen, Ortho-Est) (a salt of estrone sulfate and piperazine)
- Estrone tetraacetylglucoside (Glucovex, Glycovex)
Never marketed
Other estrone esters which are notable but have not been marketed include:
- Estrone cyanate
- Estrone glucuronide
- Estrone sulfamate (EMATE; estrone-3-O-sulfamate)
Estriol esters
Marketed
Esters of estriol that have been marketed include:[1][2]
- Estriol 3-glucuronide (as a component of Emmenin and Progynon)
- Estriol diacetate benzoate (Holin-Depot)
- Estriol glucuronide (as a component of Emmenin and Progynon)
- Estriol sulfate glucuronide (a component of Emmenin and Progynon)
- Estriol succinate (Sinapause, Styptanon, Synapause)
- Estriol sodium succinate (Pausan, Styptanon)
- Estriol tripropionate (Estriel)
- Estriol sulfate (as a component of Emmenin and Progynon)
Never marketed
The following ester of estriol was never marketed:
Esters of other steroidal estrogens
Marketed
The following esters of other estrogens exist and have been marketed:[1]
- Cloxestradiol acetate (Genovul) – the O,O-diacetate ester of cloxestradiol
- Ethinylestradiol sulfonate (Turisteron) – the 3-isopropylsulfonate ester of ethinylestradiol
- Hydroxyestrone diacetate (Colpoginon, Colpormon, Hormobion, Hormocervix) – the 3,16α-diacetate ester of 16α-hydroxyestrone
Ethers of steroidal estrogens
Marketed
A number of estrogen ethers also exist and have been marketed, including:[5][1]
- Clomestrone (Arterolo, Atheran, Colesterel, Iposclerone, Liprotene, Persclerol) – the 3-methyl ether of the 16α-chlorinated derivative of estrone
- Mestranol (Devocin, Ovastol, Tranel) (component of Enovid, Enavid, Ortho-Novin, Femigen, Norbiogest) – the 3-methyl ether of ethinylestradiol
- Moxestrol (Surestryl) – the 11-methyl ether of the 11β-methyl 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:[5]
- Mytatrienediol – the 3-methyl ether of the 16α-methylated derivative of 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:
- Diethylstilbestrol diacetate (Hormostilboral Stark)
- Diethylstilbestrol dilaurate (Acnestrol-Lotion)
- Diethylstilbestrol dipalmitate (stilpalmitate) (Palmestril, Stilpalmitate)
- Diethylstilbestrol disulfate (Hydroestryl, Idroestril)
Never marketed
- Furostilbestrol (diethylstilbestrol difuroate)
As well as the following nitrogen mustard ester:
- ICI-85966 (Stilbostat; diethylstilbestrol bis(di(2-chloroethyl)carbamate))
Hexestrol esters
Marketed
- Hexestrol diacetate (Retalon Lingual, Robal, Sintestrol, Sintofolin)
- Hexestrol dicaprylate (dioctanoylhexestrol) (Taston)
- Hexestrol diphosphate (Cytostesin, Pharmestrin, Retalon Aquosum)
- Hexestrol dipropionate (Hexanoestrol, Retalon Oleosum)
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
- Dienestrol diacetate (Faragynol, Gynocyrol)
- Methestrol dipropionate (promethestrol dipropionate, dimethylhexestrol dipropionate) (Meprane Dipropionate)
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 2 3 4 5 6 7 Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 404. ISBN 978-3-88763-075-1. Retrieved 29 May 2012.
- 1 2 3 4 5 6 7 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.
- ↑ 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.
- ↑ Luisi M, Kicovic PM, Alicicco E, Franchi F (1978). "Effects of estradiol decanoate in ovariectomized women". J. Endocrinol. Invest. 1 (2): 101–6. PMID 755846. doi:10.1007/BF03350355.
- 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.