Estradiol ester
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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 oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...
prodrug A prodrug is a 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 used to improve how the dru ...
s of
estrogen Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal ac ...
s. It includes esters, as well as
ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again ...
s, of
steroid A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and ...
al
estrogen Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal ac ...
s like
estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development o ...
,
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 potent nonsteroidal estrogen derivatives that includes, most notably, dieth ...
s
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 ...
.


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.https://www.accessdata.fda.gov/drugsatfda_docs/label/ ...
(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 th ...
(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 cis women, in hormone therapy for trans women, and in ...
(Depo-Estradiol, Depofemin, Estradep; Cyclofem, Lunelle) *
Estradiol dipropionate Estradiol dipropionate (EDP), sold under the brand names Agofollin, Di-Ovocylin, and Progynon DP among others, is an estrogen medication which has been used in hormone therapy for menopausal symptoms and low estrogen levels in women and in the t ...
(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 wi ...
(Perlutal, Topasel, Unalmes, Yectames) *
Estradiol undecylate Estradiol undecylate (EU or E2U), also known as estradiol undecanoate and formerly sold under the brand names Delestrec and Progynon Depot 100 among others, is an estrogen medication which has been used in the treatment of prostate cancer in men. ...
(Delestrec, Progynon Depot) *
Estradiol valerate Estradiol valerate (EV), sold for use by mouth under the brand name Progynova and Primiwal E4 and for use by injection under the brand names Delestrogen and Progynon Depot among others, is an estrogen medication. It is used in hormone therapy fo ...
(Delestrogen, Progynon Depot, Progynova; Gravibinon, Mesigyna, Mesygest) *
Polyestradiol phosphate Polyestradiol phosphate (PEP), sold under the brand name Estradurin, is an estrogen medication which is used primarily in the treatment of prostate cancer in men. It is also used in women to treat breast cancer, as a component of hormone therapy ...
(Estradurin) (an estradiol ester in
polymer A polymer (; Greek '' poly-'', "many" + '' -mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...
ic form) And the following less commonly used esters: *
Cloxestradiol acetate Cloxestradiol acetate (brand name Genovul), also known as 17-(2,2,2-trichloroethoxy)estradiol ''O'',''O''-diacetate, is a synthetic steroidal estrogen derived from estradiol. It is the ''O'',''O''-diacetate ester of cloxestradiol Cloxestradiol ...
(Genovul; diacetate ester of
cloxestradiol Cloxestradiol (), also known as 17-(2,2,2-trichloroethoxy)estradiol, is a synthetic, steroidal estrogen which was never marketed. It is an analogue of estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and th ...
, 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 is ...
(Redimen, Soluna, Unijab, Unimens) *
Estradiol butyrylacetate Estradiol butyrylacetate (EBA), sold under the brand names Follikosid and Klimanosid-R Depot (with testosterone ketolaurate and reserpine), is an estrogen medication which is no longer marketed. It is an estrogen ester, specifically, an ester of ...
(Follikoside) *
Estradiol dibutyrate Estradiol dibutyrate (EDBu), or estradiol dibutanoate, is an estrogen medication and an estrogen ester – specifically, a diester of estradiol – which is no longer used. It was a component of Triormon Depositum, a combination formulation F ...
(Triormon Depositum) *
Estradiol dienantate Estradiol dienanthate (EDE), sold under the brand names Climacteron among others, is a long-acting estrogen medication which was previously used in menopausal hormone therapy for women and to suppress lactation in women. It was formulated in com ...
(Climacteron, Lactimex, Lactostat) *
Estradiol diundecylate Estradiol diundecylate (brand name Estrolent), or estradiol diundecanoate, also known as 17β-estradiol 3,17β-diundecylate, is an estrogen and an estrogen ester – specifically, the 3,17β-di undecylate ester of estradiol – which has been ma ...
(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 Estradiol furoate (EF), or estradiol 17β-furoate, sold under the brand name Di-Folliculine, is an estrogen medication and estrogen ester which is no longer marketed. It is the C17β furoate ester of estradiol. Estradiol benzoate has also be ...
(Di-Folliculine) *
Estradiol hemisuccinate Estradiol hemisuccinate (brand name Eutocol), or simply estradiol succinate, also known as estradiol 17β-hemisuccinate, is an estrogen medication and an estrogen ester – specifically, the hemisuccinate ester of estradiol. It is used as a c ...
(Eutocol; Hosterona) *
Estradiol hexahydrobenzoate Estradiol hexahydrobenzoate (EHHB), sold under a number of brand names including Benzo-Ginoestril A.P., BenzoGynoestryl Retard, Ginestryl-15-Depot, Menodin, and Tardoginestryl, is an estrogen medication which was previously used for indications ...
(Benzo-Ginoestril A.P., BenzoGynoestryl Retard, Ginestryl-15-Depot, Menodin, Tardoginestryl) * Estradiol palmitate (Esmopal) *
Estradiol phenylpropionate Estradiol phenylpropionate (EPP), also known as estradiol 17β-phenylpropionate and sold under the brand name Menformon Prolongatum, is an estrogen which is no longer marketed. It is an estrogen ester, specifically the C17β phenylpropionate est ...
(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 Estradiol sulfate (E2S), or 17β-estradiol 3-sulfate, is a natural, endogenous steroid and an estrogen ester. E2S itself is biologically inactive, but it can be converted by steroid sulfatase (also called estrogen sulfatase) into estradiol, which ...
(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 the ...
(Premarin)) The following
nitrogen mustard Nitrogen mustards are cytotoxic organic compounds with the chloroethylamine (Cl(CH2)2NR2) functional group. Although originally produced as chemical warfare agents, they were the first chemotherapeutic agents for treatment of cancer. Nitrogen ...
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 and chemotherapy medication which is used in the treatment of prostate cancer in men. It is taken ...
(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 acetylsalicylate, or estradiol 3-acetylsalicylate, is a synthetic estrogen and estrogen ester – specifically, the C3 acetylsalicylic acid (aspirin) ester of estradiol – which was described in the late 1980s and was never marketed. I ...
(estradiol 3-acetylsalicylate) * Estradiol anthranilate (estradiol 3-anthranilate) * Estradiol arachidonate * Estradiol benzoate cyclooctenyl ether (estradiol 3-benzoate 17β-cyclooctenyl ether; EBCO) *
Estradiol caprylate Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development of ...
(estradiol octanoate) *
Estradiol cyclooctyl acetate Estradiol cyclooctyl acetate (E2COA), or estradiol 17β-cyclooctylacetate, also known as estra-1,3,5(10)-triene-3,17β-diol 17β-cyclooctylacetate, is an estrogen medication and an estrogen ester – specifically, the 17β- cyclooctylacetate este ...
(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 t ...
* Estradiol sulfate glucuronide *
Estradiol linoleate Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development of ...
* Estradiol oleate * Estradiol phosphate *
Estradiol salicylate Estradiol salicylate, or estradiol 3-salicylate, is a synthetic estrogen and estrogen ester – specifically, the C3 salicylic acid ester of estradiol – which was described in the late 1980s and was never marketed. It is a metabolite of estrad ...
(estradiol 3-salicylate) *
Estradiol sulfamate Estradiol sulfamate (E2MATE; developmental code names J995, PGL-2, PGL-2001, ZK-190628, others), or estradiol-3-''O''-sulfamate, is a steroid sulfatase (STS) inhibitor which is under development for the treatment of endometriosis. It is the C3 su ...
(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 Alestramustine (), also known as estradiol 3-(''bis''(2-chloroethyl)carbamate) 17β-(L-alaninate), is a cytostatic antineoplastic agent which was never marketed. It is the L-alanine ester of estramustine, which is a combination of the nitrogen ...
(estradiol 3-(bis(2-chloroethyl)carbamate), 17-ester with L-alanine) * Atrimustine (KM-2210; bestrabucil, busramustine) * Estradiol mustard (NSC-112259; chlorphenacyl estradiol diester) *
Estramustine Estramustine (, , ) is an estrogen and cytostatic antineoplastic agent which was never marketed. It is an estrogen ester – specifically, the C3 normustine ester of estradiol – and acts in part as a prodrug of estradiol in the body. Estramus ...
(Leo 275; Ro 21-8837) *
Estromustine Estromustine (developmental code name Leo 271 f), also known as estrone 17β-3-N-bis(2-chloroethyl)carbamate or estrone–cytostatic complex, is a major active metabolite of the cytostatic antineoplastic agent and estrogen estramustine phospha ...
(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 menop ...
(as the primary component 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 the ...
(Premarin)) **
Estropipate Estropipate, also known as piperazine estrone sulfate and sold under the brand names Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others, is an estrogen medication which is used mainly in menopausal hormone therapy in the treatmen ...
(Ogen, Ortho-Est) (a salt of estrone sulfate and
piperazine Piperazine () is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. Piperazine exists as small alkaline deliquescent crystals with a saline taste. The piperazines are a broad ...
) * 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 (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 ...
* Estrone sulfamate (EMATE; J994; estrone-3-O-sulfamate) * Estrone oleate


Estriol esters


Marketed

Esters of estriol that have been marketed include: *
Estriol 3-glucuronide Estriol 3-glucuronide, or oestriol 3-glucuronide, also known as estriol 3-β-D-glucosiduronic acid, is a natural, steroidal estrogen and a glucuronic acid (β-D-glucopyranuronic acid) conjugate of estriol. It is found in the urine of women as a ...
(as a component of
conjugated estriol Conjugated estriol, sold under the brand names Progynon and Emmenin, is an estrogen (medication), estrogen medication which was previously used for estrogen-type indications such as the treatment of menopausal symptoms in women. The term specifi ...
(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 Conjugated estriol, sold under the brand names Progynon and Emmenin, is an estrogen (medication), estrogen medication which was previously used for estrogen-type indications such as the treatment of menopausal symptoms in women. The term specifi ...
(Emmenin, Progynon)) * Estriol succinate (Sinapause, Styptanon, Synapause) ** Estriol sodium succinate (Pausan, Styptanon) *
Estriol sulfate Estriol sulfate, or estriol 3-sulfate, is a conjugated metabolite of estriol that is present in high quantities during pregnancy. It is formed from estriol in the liver and is eventually excreted in the urine by the kidneys. It has much higher ...
(as a component of
conjugated estriol Conjugated estriol, sold under the brand names Progynon and Emmenin, is an estrogen (medication), estrogen medication which was previously used for estrogen-type indications such as the treatment of menopausal symptoms in women. The term specifi ...
(Emmenin, Progynon)) * Estriol sulfate glucuronide (as a component of
conjugated estriol Conjugated estriol, sold under the brand names Progynon and Emmenin, is an estrogen (medication), estrogen medication which was previously used for estrogen-type indications such as the treatment of menopausal symptoms in women. The term specifi ...
(Emmenin, Progynon)) * Estriol tripropionate (Estriel) *
Polyestriol phosphate Polyestriol phosphate (PE3P, SEP), sold under the brand names Gynäsan, Klimadurin, and Triodurin, is an estrogen medication which was previously used in menopausal hormone therapy (i.e., to treat menopausal symptoms in postmenopausal women) an ...
(Gynäsan, Klimadurin, Triodurin) (an estriol ester in
polymer A polymer (; Greek '' poly-'', "many" + '' -mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...
ic form)


Never marketed

The following ester of estriol was never marketed: *
Estriol dihexanoate Estriol dihexanoate, or estriol 3,17β-dihexanoate, is a synthetic compound, synthetic estrogen (medication), estrogen and estrogen ester – specifically, the C3 and C17β hexanoate, dihexanoate ester of estriol (medication), estriol – which w ...
*
Estriol dipropionate Estriol dipropionate, or estriol 3,17β-dipropionate, is a synthetic estrogen and estrogen ester – specifically, the C3 and C17β dipropionate ester of estriol – which was first described in 1963 and was never marketed. Following a single ...
* 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. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disord ...
exist and have been marketed: *
Ethinylestradiol sulfonate Ethinylestradiol sulfonate (EES), sold under the brand names Deposiston and Turisteron among others, is an estrogen (medication), estrogen medication which has been used in birth control pills for women and in the treatment of prostate cancer in ...
(Turisteron; ethinylestradiol 3-isopropylsulfonate)


Never marketed

* Ethinylestradiol benzoate – the 3-benzoate ester of
ethinylestradiol Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disord ...
* Ethinylestradiol ''N'',''N''-diethylsulfamate (J271) – the 3-(''N'',''N''-diethyl)sulfamate ester of
ethinylestradiol Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disord ...
*
Ethinylestradiol pyrrolidinosulfonate Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disor ...
(J272) – the 3-pyrrolidinosulfonate ester of
ethinylestradiol Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disord ...
* Ethinylestradiol sulfamate (J1028) – the 3-sulfamate ester of
ethinylestradiol Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disord ...
* Ethinylestradiol sulfate


Esters of other steroidal estrogens


Marketed

The following esters of other estrogens exist and have been marketed: * Hydroxyestrone diacetate (Colpoginon, Colpormon, Hormobion, Hormocervix) – the 3,16α-diacetate ester of 16α-hydroxyestrone


Ethers of steroidal estrogens


Marketed

A number of estrogen ''
ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again ...
s'' also exist and have been marketed, including: * Clomestrone (Arterolo, Atheran, Colesterel, Iposclerone, Liprotene, Persclerol) – the 3-methyl ether of 16α-chloroestrone *
Cloxestradiol acetate Cloxestradiol acetate (brand name Genovul), also known as 17-(2,2,2-trichloroethoxy)estradiol ''O'',''O''-diacetate, is a synthetic steroidal estrogen derived from estradiol. It is the ''O'',''O''-diacetate ester of cloxestradiol Cloxestradiol ...
(Genovul) – the ''O'',''O''-diacetate ester of
cloxestradiol Cloxestradiol (), also known as 17-(2,2,2-trichloroethoxy)estradiol, is a synthetic, steroidal estrogen which was never marketed. It is an analogue of estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and th ...
(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 i ...
(Devocin, Ovastol, Tranel) (component of Enovid, Enavid, Ortho-Novin, Femigen, Norbiogest) – the 3-methyl ether of
ethinylestradiol Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disord ...
*
Moxestrol Moxestrol, sold under the brand name Surestryl, is an estrogen medication which has been used in Europe for the treatment of menopausal symptoms and menstrual disorders. It is taken by mouth. In addition to its use as a medication, moxestrol has ...
(Surestryl) – the 11β-methoxy derivative of
ethinylestradiol Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disord ...
(and hence the 11β-methyl ether of the 11β-hydroxyl derivative of ethinylestradiol) *
Nilestriol Nilestriol () (brand name Wei Ni An; developmental code name LY-49825), also known as nylestriol (, ), is a synthetic estrogen which was patented in 1971 and is marketed in China. It is the 3-cyclopentyl ether of ethinylestriol, and is also k ...
(Wei Ni An) – the 3-cyclopentyl ether of
ethinylestriol Ethinylestriol (EE3), or 17α-ethynylestriol, also known as 17α-ethynylestra-1,3,5(10)-triene-3,16α,17β-triol, is a synthetic estrogen which was never marketed. Nilestriol, the 3-cyclopentyl ether of ethinylestriol, is a prodrug of ethinyle ...
* Promestriene (Colpotrofin, Colpotrophine, Delipoderm) – the 3-propyl and 17β-methyl diether of
estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development o ...
* Quinestradol (Colpovis, Colpovister, Pentovis) – the 3-cyclopentyl ether of
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 ...
*
Quinestrol Quinestrol, also known as ethinylestradiol cyclopentyl ether (EECPE), sold under the brand name Estrovis among others, is an estrogen medication which has been used in menopausal hormone therapy, hormonal birth control, and to treat breast cancer ...
(Agalacto-Quilea, Basaquines, Eston, Estrovis, Estrovister, Plestrovis, Qui-lea) – the 3-cyclopentyl ether of
ethinylestradiol Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disord ...


Never marketed

A few other estrogen ethers which are notable but have not been marketed include: *
Cloxestradiol Cloxestradiol (), also known as 17-(2,2,2-trichloroethoxy)estradiol, is a synthetic, steroidal estrogen which was never marketed. It is an analogue of estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and th ...
– the 17β-chloral hemiacetal ether of
estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development o ...
* Estradiol benzoate cyclooctenyl ether – the 17β-cyclooctenyl ether of estradiol 3-benzoate * Estradiol 3-saccharinylmethyl ether – the 3-(saccharinylmethyl) ether of
estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development o ...
* Estradiol 3-tetrahydropyranyl ether – the 3-(tetrahydropyran-2-yl) ether of
estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development o ...
* Estradiol 17β-tetrahydropyranyl ether – the 17β-(tetrahydropyran-2-yl) ether of
estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development o ...
* Estrone methyl ether – the 3-methyl ether of
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 ...
* 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 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 on ...
(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 Diethylstilbestrol dipalmitate (brand names Palmestril, Stilpalmitate), also known as stilpalmitate, is a synthetic, nonsteroidal estrogen of the stilbestrol group and an ester of diethylstilbestrol (DES) that was formerly marketed but is now no l ...
(stilpalmitate) (Palmestril, Stilpalmitate) *
Diethylstilbestrol disulfate Diethylstilbestrol disulfate (brand names Hydroestryl, Idroestril; former developmental code name M.G. 137) is a synthetic, nonsteroidal estrogen of the stilbestrol group and an ester of diethylstilbestrol Diethylstilbestrol (DES), also known a ...
(Hydroestryl, Idroestril)


Never marketed

* Diethylstilbestrol sulfate * Furostilbestrol (diethylstilbestrol difuroate) *
Polydiethylstilbestrol phosphate Polydiethylstilbestrol phosphate (PSP, PDSP) is an estrogen (medication), 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 ...
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 Hexestrol dicaprylate (brand name Taston), or dioctanoylhexestrol, is a synthetic, nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol that is no longer marketed. It is a long-acting ester of hexestrol. See also * Hexestr ...
(dioctanoylhexestrol) (Taston) *
Hexestrol diphosphate Hexestrol diphosphate (brand names Cytostatin, Cytostesin, Pharmestrin, Retalon Aquosum) is a synthetic, nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol and used as an estrogen and antineoplastic agent in the treatm ...
(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 Phenestrol, or fenestrol, also known as hexestrol bis -[bis(2-chloroethyl)aminohenylacetate, is a synthetic compound">synthetic, nonsteroidal estrogen and cytostatic antineoplastic agent (i.e., chemotherapy drug) and a chlorine, chlorphenyl group, ...
(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

*
List of estrogens This is a list of steroidal estrogens or derivatives of estradiol, estrone, and estriol. Most esters of these estrogens are not included in this list; for esters, see here instead. Estradiol derivatives 17α-Substituted estradiol derivative ...
*
List of progestogen esters This is a list of progestogen esters, or esters of progestogens.http://www.micromedexsolutions.com Unlike the case of testosterone and estradiol, progesterone cannot be esterified as it lacks hydroxyl groups, so all progestogen esters, with ...
*
List of androgen esters This is a list of androgen esters, including esters (as well as ethers) of natural androgens like testosterone and dihydrotestosterone (DHT) and synthetic anabolic–androgenic steroids (AAS) like nandrolone (19-nortestosterone). Esters of n ...
*
List of combined sex-hormonal preparations This is a list of known combined sex-hormonal formulations. Brand names and developmental code names are in parentheses. Androgens Injection Marketed * Nandrolone decanoate/nandrolone phenylpropionate (Dinandrol) * Testosterone propionate/ ...


References

{{Estrogen receptor modulators Estrogen esters Estrogens Prodrugs