This is a list of

estrogen ester An estrogen ester is an ester of an estrogen, most typically of estradiol but also of other estrogens such as estrone, estriol, and even nonsteroidal estrogens like diethylstilbestrol. Esterification renders estradiol into a prodrug of estradiol ...

s, or

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

prodrug A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be ...

s of

estrogen Estrogen (also spelled oestrogen in British English; see spelling differences) is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three ...

s. It includes esters, as well as

ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...

s, of

steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...

s like

estradiol Estradiol (E2), also called oestrogen, oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible ...

estrone Estrone (E1), also spelled oestrone, is a steroid, a weak estrogen, and a minor female sex hormone. It is one of three major endogenous estrogens, the others being estradiol and estriol. Estrone, as well as the other estrogens, are synthesized ...

, and

estriol Estriol (E3), also spelled oestriol, is a steroid, a weak estrogen, and a minor female sex hormone. It is one of three major endogenous estrogens, the others being estradiol and estrone. Levels of estriol in women who are not pregnant are almost ...

and of

nonsteroidal estrogen A nonsteroidal estrogen is an estrogen with a nonsteroidal chemical structure. The most well-known example is the stilbestrol estrogen diethylstilbestrol (DES). Although nonsteroidal estrogens formerly had an important place in medicine, they ha ...

s like the

stilbestrol Stilbestrol, or stilboestrol, also known as 4,4'-dihydroxystilbene or 4,4'-stilbenediol, is a stilbenoid nonsteroidal estrogen and the parent compound of a group of more potency (pharmacology), potent nonsteroidal estrogen chemical derivative, de ...

diethylstilbestrol Diethylstilbestrol (DES), also known as stilbestrol or stilboestrol, is a nonsteroidal estrogen medication, which is presently rarely used. In the past, it was widely used for a variety of indications, including pregnancy support for those with ...

and

hexestrol Hexestrol, sold under the brand name Synestrol among others, is a nonsteroidal estrogen which was previously used for estrogen replacement therapy and in the treatment of certain hormone-dependent cancers as well as gynecological disorders but is ...

Esters of steroidal estrogens

Estradiol esters

Marketed

Many esters of estradiol have been marketed, including the following major esters: *

Estradiol acetate Estradiol acetate (EA), sold under the brand names Femtrace, Femring, and Menoring, is an estrogen medication which is used in hormone therapy for the treatment of menopausal symptoms in women. It is taken by mouth once daily or given as a vagin ...

(Femring, Femtrace, Menoring) *

Estradiol benzoate Estradiol benzoate (EB), sold under the brand name Progynon-B among others, is an estrogen medication which is used in hormone therapy for menopausal symptoms and low estrogen levels in women, in hormone therapy for transgender women, and in the ...

(Agofollin Depot, Progynon-B; Duogynon, Primosiston, Sistocyclin) *

Estradiol cypionate Estradiol cypionate (EC), sold under the brand name Depo-Estradiol among others, is an estrogen medication which is used in hormone therapy for menopausal symptoms and low estrogen levels in women, in hormone therapy for trans women, and in horm ...

(Depo-Estradiol, Depofemin, Estradep; Cyclofem, Lunelle) * Estradiol dipropionate (Agofollin, Di-Ovocyclin, Progynon-DP; EP Hormone Depot) *

Estradiol enantate Estradiol enantate (EEn or E2-EN), also spelled estradiol enanthate and sold under the brand names Perlutal and Topasel among others, is an estrogen medication which is used in hormonal birth control for women. It is formulated in combination wit ...

(Perlutal, Topasel, Unalmes, Yectames) *

Estradiol undecylate Estradiol undecylate (EU, EUn, E2U), also known as estradiol undecanoate and formerly sold under the brand names Delestrec and Progynon Depot 100 among others, is an estrogen (medication), estrogen medication which has been used in the treatment ...

(Delestrec, Progynon Depot) *

Estradiol valerate Estradiol valerate (EV), sold for use oral administration, by mouth under the brand name Progynova and for use by injection (medicine), injection under the brand names Delestrogen and Progynon Depot among others, is an estrogen (medication), es ...

(Delestrogen, Progynon Depot, Progynova; Gravibinon, Mesigyna, Mesygest) * Polyestradiol phosphate (Estradurin) (an estradiol ester in

polymer A polymer () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their br ...

ic form) And the following less commonly used esters: * Cloxestradiol acetate (Genovul; diacetate ester of cloxestradiol, or estradiol 17β-chloral hemiacetal ether) *

Estradiol benzoate butyrate Estradiol benzoate butyrate (EBB), sold under the brand names Neolutin N, Redimen, Soluna, and Unijab and formerly known under the developmental code name Unimens, is an estrogen medication which is used in hormonal birth control for women. It i ...

(Redimen, Soluna, Unijab, Unimens) * Estradiol butyrylacetate (Follikoside) * Estradiol dibutyrate (Triormon Depositum) * Estradiol dienantate (Climacteron, Lactimex, Lactostat) * Estradiol diundecylate (Estrolent; Trioestrine Retard) *

Estradiol diundecylenate Estradiol diundecylenate (brand name Etrosteron), or estradiol diundecenoate, also known as 17β-estradiol 3,17β-diundec-10-enoate, is a semisynthetic steroidal estrogen and an estrogen ester – specifically, the 3,17β-di undecylenate ester ...

(Etrosteron) * Estradiol furoate (Di-Folliculine) * Estradiol hemisuccinate (Eutocol; Hosterona) * Estradiol hemihydrate (Estrofem) * Estradiol hexahydrobenzoate (Benzo-Ginoestril A.P., BenzoGynoestryl Retard, Ginestryl-15-Depot, Menodin, Tardoginestryl) * Estradiol palmitate (Esmopal) * Estradiol phenylpropionate (Dimenformon Prolongatum; Estandron Prolongatum, Lynandron Prolongatum, Mixogen) * Estradiol pivalate (Estrotate; Estrotate with Progesterone) * Estradiol propionate (estradiol 17β-propionate) (Acrofollin, Akrofollin, Follhormon) * Estradiol propoxyphenylpropionate (Durovex) * Estradiol stearate (Depofollan) * Estradiol sulfate (a minor constituent of

conjugated estrogens Conjugated estrogens (CEs), or conjugated equine estrogens (CEEs), sold under the brand name Premarin among others, is an estrogen medication which is used in menopausal hormone therapy and for various other indications. It is a mixture of th ...

(Premarin)) The following

nitrogen mustard Nitrogen mustards (NMs) are cytotoxic organic compounds with the bis(2-chloroethyl)amino ((ClC2H4)2NR) functional group. Although originally produced as chemical warfare agents, they were the first chemotherapeutic agents for treatment of canc ...

ester of estradiol is a cytostatic antineoplastic agent and has been marketed: *

Estramustine phosphate Estramustine phosphate (EMP), also known as estradiol normustine phosphate and sold under the brand names Emcyt and Estracyt, is a dual estrogen (medication), estrogen and chemotherapy medication which is used in the treatment of prostate cancer ...

(Emcyt, Estracyt; estradiol 3-normustine 17β-phosphate)

Never marketed

A number of other estradiol esters which have not been marketed include: * Estradiol 3-furoate * Estradiol 3-propionate (''not to be confused with estradiol monopropionate (estradiol 17β-propionate)'') * Estradiol 17β-(1-(4-(aminosulfonyl)benzoyl)--proline) (EC508)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 * Estradiol 17β-acetate * Estradiol 17β-benzoate * Estradiol acetylsalicylate (estradiol 3-acetylsalicylate) * Estradiol anthranilate (estradiol 3-anthranilate) * Estradiol arachidonate * Estradiol benzoate cyclooctenyl ether (estradiol 3-benzoate 17β-cyclooctenyl ether; EBCO) * Estradiol caprylate (estradiol octanoate) * Estradiol cyclooctyl acetate (E2CoA) * Estradiol decanoate (estradiol 17β-decanoate) * Estradiol diacetate * Estradiol dibenzoate * Estradiol dicypionate * Estradiol dioleate * Estradiol dipalmitate * Estradiol distearate * Estradiol disulfate *

Estradiol glucuronide Estradiol glucuronide, or estradiol 17β-D-glucuronide, is a conjugated metabolite of estradiol. It is formed from estradiol in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by ...

Estradiol sulfate glucuronide Estradiol (E2), also called oestrogen, oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible for ...

* Estradiol linoleate * Estradiol oleate *

Estradiol phosphate Estradiol phosphate, or estradiol 17β-phosphate, also known as estra-1,3,5(10)-triene-3,17β-diol 17β-(dihydrogen phosphate), is an estrogen which was never marketed. It is an estrogen ester, specifically an ester of estradiol with phosphoric ...

* 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: * Estrone acetate (Hovigal) *

Estrone sulfate Estrone sulfate, also known as E1S, E1SO4 and estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate. In addition to its role as a natural hormone, estrone sulfate is used as a medication, for instance in men ...

(as the primary component of

(Premarin)) ** Estropipate (Ogen, Ortho-Est) (a salt of estrone sulfate and

piperazine Piperazine () is an organic compound with the formula . In term of its structure, it can be described as cyclohexane with the 1- and 4-CH2 groups replaced by NH. Piperazine exists as deliquescent solid with a saline taste. Piperazine is freely sol ...

) * Estrone tetraacetylglucoside (Glucovex, Glycovex)

Never marketed

Other estrone esters which are notable but have not been marketed include: * Estrone benzoate * Estrone cyanate * Estrone enanthate * Estrone enanthate benzilic acid hydrazone *

Estrone glucuronide Estrone glucuronide, or estrone-3-D-glucuronide, is a conjugated metabolite of estrone. It is formed from estrone in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by the kidneys ...

* Estrone phosphate * Estrone propionate * Estrone sulfamate (EMATE; J994; estrone-3-O-sulfamate) * Estrone oleate

Estriol esters

Marketed

Esters of estriol that have been marketed include: * Estriol 3-glucuronide (as a component of conjugated estriol (Emmenin, Progynon)) * Estriol acetate benzoate (Holin-Depot) *

Estriol glucuronide Estriol glucuronide (E3G), or oestriol glucuronide, also known as estriol monoglucuronide, as well as estriol 16α-β-D-glucosiduronic acid, is a natural, steroidal estrogen and the glucuronic acid (β-D-glucopyranuronic acid) conjugate of estri ...

(as a component of conjugated estriol (Emmenin, Progynon)) * Estriol succinate (Sinapause, Styptanon, Synapause) ** Estriol sodium succinate (Pausan, Styptanon) * Estriol sulfate (as a component of conjugated estriol (Emmenin, Progynon)) * Estriol sulfate glucuronide (as a component of conjugated estriol (Emmenin, Progynon)) * Estriol tripropionate (Estriel) * Polyestriol phosphate (Gynäsan, Klimadurin, Triodurin) (an estriol ester in

ic form)

Never marketed

The following ester of estriol was never marketed: * Estriol dihexanoate * Estriol dipropionate * Estriol phosphate (E3P) * Estriol sulfamate (E3MATE; J1034; estriol-3-O-sulfamate) * Estriol triacetate

Ethinylestradiol esters

Marketed

The following esters of

ethinylestradiol Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. Ethinylestradiol was widely used for various indications such as the treatment of menopausal symptoms, gynecological ...

exist and have been marketed: * Ethinylestradiol sulfonate (Turisteron; ethinylestradiol 3-isopropylsulfonate)

Never marketed

* Ethinylestradiol benzoate – the 3-benzoate ester of

* Ethinylestradiol ''N'',''N''-diethylsulfamate (J271) – the 3-(''N'',''N''-diethyl)sulfamate ester of

* Ethinylestradiol pyrrolidinosulfonate (J272) – the 3-pyrrolidinosulfonate ester of

* Ethinylestradiol sulfamate (J1028) – the 3-sulfamate ester of

Ethinylestradiol sulfate Ethinylestradiol sulfate (EE sulfate), also known as 17α-ethynylestradiol 3-sulfate, is an estrogen ester – specifically, the C3 sulfuric acid (sulfate) ester of the synthetic estrogen ethinylestradiol (EE) – and is the major metabolite of ...

Esters of other steroidal estrogens

Marketed

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

Hydroxyestrone diacetate Hydroxyestrone diacetate (brand names Colpoginon, Colpormon, Hormobion, Hormocervix) (former developmental code name RD-310), or 16α-hydroxyestrone diacetate, also known as 3,16α-dihydroxyestra-1,3,5(10)-trien-17-one 3,16α-diacetate, is a synt ...

(Colpoginon, Colpormon, Hormobion, Hormocervix) – the 3,16α-diacetate ester of 16α-hydroxyestrone

Ethers of steroidal estrogens

Marketed

A number of estrogen ''

s'' also exist and have been marketed, including: * 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 Mestranol, sold under the brand names Enovid, Norinyl, and Ortho-Novum among others, is an estrogen medication which has been used in birth control pills, menopausal hormone therapy, and the treatment of menstrual disorders. It is formulated in ...

(Devocin, Ovastol, Tranel) (component of Enovid, Enavid, Ortho-Novin, Femigen, Norbiogest) – the 3-methyl ether of

* Moxestrol (Surestryl) – the 11β-methoxy derivative of

(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

Quinestradol Quinestradol (, ) (brand names Colpovis, Colpovister, Pentovis), also known as quinestradiol or quinestriol, as well as estriol 3-cyclopentyl ether (E3CPE), is a synthetic compound, synthetic estrogen (medication), estrogen and estrogen ether wh ...

(Colpovis, Colpovister, Pentovis) – the 3-cyclopentyl ether of

* Quinestrol (Agalacto-Quilea, Basaquines, Eston, Estrovis, Estrovister, Plestrovis, Qui-lea) – the 3-cyclopentyl ether of

Never marketed

A few other estrogen ethers which are notable but have not been marketed include: * Cloxestradiol – the 17β-chloral hemiacetal ether of

* Estradiol benzoate cyclooctenyl ether – the 17β-cyclooctenyl ether of estradiol 3-benzoate * Estradiol 3-saccharinylmethyl ether – the 3-(saccharinylmethyl) ether of

Estradiol 3-tetrahydropyranyl ether Estradiol 3-tetrahydropyranyl ether is a synthetic estrogen and estrogen ether which was never marketed. It has been reported to possess improved oral activity relative to estradiol Estradiol (E2), also called oestrogen, oestradiol, is an es ...

– the 3-(tetrahydropyran-2-yl) ether of

* Estradiol 17β-tetrahydropyranyl ether – the 17β-(tetrahydropyran-2-yl) ether of

* Estrone methyl ether – the 3-methyl ether of

Mytatrienediol Mytatrienediol (developmental code name SC-6924; former tentative brand names Manvene, Anvene), also known as 16α-methyl-16β-epiestriol 3-methyl ether or 16β-hydroxy-16α-methylestradiol 3-methyl ether, is a synthetic steroidal estrogen medica ...

– 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 Fosfestrol, sold under the brand name Honvan and also known as diethylstilbestrol diphosphate (DESDP), is an estrogen medication which is used in the treatment of prostate cancer in men. It is given by slow intravenous infusion once per day to o ...

(diethylstilbestrol diphosphate) (Honvan, Difostilben, Fosfostilben, Fostrolin, Stilbol, Stilphostrol, Vagestrol) Less commonly used esters of diethylstilbestrol include: * Diethylstilbestrol diacetate (Hormostilboral Stark) *

Diethylstilbestrol dilaurate Diethylstilbestrol dilaurate (brand name Acnestrol-Lotion) is a synthetic, nonsteroidal estrogen of the stilbestrol group and an ester of diethylstilbestrol (DES) that was previously marketed but is now no longer available. It was formulated and ...

(Acnestrol-Lotion) * Diethylstilbestrol dipalmitate (stilpalmitate) (Palmestril, Stilpalmitate) * Diethylstilbestrol disulfate (Hydroestryl, Idroestril)

Never marketed

* Diethylstilbestrol sulfate * Furostilbestrol (diethylstilbestrol difuroate) *

Polydiethylstilbestrol phosphate Polydiethylstilbestrol phosphate (PSP, PDSP) is an estrogen medication which has been used in scientific research and has been studied for use in veterinary medicine as a livestock growth promoter. It is a phosphate ester of diethylstilbestrol ( ...

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) * Hexestrol phosphate (Retalon Aquosum)

Never marketed

The following nitrogen mustard ester of hexestrol was never marketed: * Phenestrol (fenestrol; hexestrol bis -[bis(2-chloroethyl)aminohenylacetate)

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 Diethylstilbestrol monobenzyl ether (brand names Monozol, Hypantin, Pituitrope), also known as benzelstilbestrol, is a synthetic, nonsteroidal estrogen of the stilbestrol group and an ether of diethylstilbestrol (DES) that is described as a pitui ...

(benzelstilbestrol) (Monozol, Hypantin, Pituitrope) * Dimestrol (dianisylhexene, diethylstilbestrol dimethyl ether, dimethoxydiethylstilbestrol) (Depot-Ostromon, Synthila) * Mestilbol (diethylstilbestrol monomethyl ether) (Monomestro or Monomestrol)

References

{{Estrogen receptor modulators Estrogen esters Estrogens Sex hormone esters and conjugates

Esters of steroidal estrogens

Estradiol esters

Marketed

Never marketed

Estrone esters

Marketed

Never marketed

Estriol esters

Marketed

Never marketed

Ethinylestradiol esters

Marketed

Never marketed

Esters of other steroidal estrogens

Marketed

Ethers of steroidal estrogens

Marketed

Never marketed

Esters of nonsteroidal estrogens

Diethylstilbestrol esters

Marketed

Never marketed

Hexestrol esters

Marketed

Never marketed

Esters of other nonsteroidal estrogens

Marketed

Ethers of nonsteroidal estrogens

Diethylstilbestrol

Marketed

See also

References