39 Androgen esters

An androgen or anabolic steroid ester is an ester of an androgen/anabolic steroid (AAS) such as the natural testosterone or dihydrotestosterone (DHT) or the synthetic nandrolone (19-nortestosterone). Esterification renders AAS into metabolism-resistant prohormones of themselves, improving oral bioavailability, increasing lipophilicity, and extending the elimination half-life. In addition, with intramuscular injection, AAS esters are absorbed more slowly into the body, further improving the elimination half-life. Aside from differences in pharmacokinetics, these esters essentially have the same effects as the parent drugs. They are used in androgen replacement therapy (ART), among other indications. Examples of androgen esters include testosterone esters such as testosterone cypionate, testosterone enanthate, testosterone propionate, and testosterone undecanoate and nandrolone esters such as nandrolone decanoate and nandrolone phenylpropionate.

Androstenediol 3β-acetate, or 5-androstenediol 3β-acetate, also known as androst-5-ene-3β,17β-diol 3β-acetate, is a synthetic anabolic-androgenic steroid and an androgen ester – specifically, the C3β acetate ester of 5-androstenediol (androst-5-ene-3β,17β-diol) – which was never marketed.

Androstenediol 17β-acetate, or 5-androstenediol 17β-acetate, also known as androst-5-ene-3β,17β-diol 17β-acetate, is a synthetic anabolic-androgenic steroid and an androgen ester – specifically, the C17β acetate ester of 5-androstenediol (androst-5-ene-3β,17β-diol) – which was never marketed.

Androstenediol diacetate, or 5-androstenediol 3β,17β-diacetate, also known as androst-5-ene-3β,17β-diol 3β,17β-diacetate, is a synthetic anabolic-androgenic steroid and an androgen ester – specifically, the C3β,17β diacetate diester of 5-androstenediol (androst-5-ene-3β,17β-diol) – which was never marketed. The medication has been used with success to treat breast cancer in women.

Androstenediol dipropionate, or 5-androstenediol 3β,17β-dipropionate, also known as androst-5-ene-3β,17β-diol 3β,17β-dipropionate, is a synthetic anabolic–androgenic steroid and an androgen ester – specifically, the dipropionate diester of 5-androstenediol (androst-5-ene-3β,17β-diol) – which has been marketed in Europe, including in Spain, Italy, and Austria.

Androstenediol sulfate, also known as androst-5-ene-3β,17β-diol 3β-sulfate, is an endogenous, naturally occurring steroid and a urinary metabolites of androstenediol.> It is a steroid sulfate which is formed from sulfation of androstenediol by steroid sulfotransferase and can be desulfated back into androstenediol by steroid sulfatase.

Androsterone sulfate, also known as 3α-hydroxy-5α-androstan-17-one 3α-sulfate, is an endogenous, naturally occurring steroid and one of the major urinary metabolites of androgens. It is a steroid sulfate which is formed from sulfation of androsterone by the steroid sulfotransferase SULT2A1 and can be desulfated back into androsterone by steroid sulfatase.

Bolandiol dipropionate (USAN), or bolandiol propionate (JAN), also known as norpropandrolate or 19-nor-4-androstenediol dipropionate, as well as estr-4-ene-3β,17β-diol 3,17-dipropionate, is a synthetic anabolic-androgenic steroid (AAS) and derivative of 19-nortestosterone (nandrolone). It is an androgen ester – specifically, the 3,17-dipropionate ester of bolandiol (19-nor-4-androstenediol).

Bolazine capronate (INN), also known as bolazine caproate or bolazine hexanoate, as well as di(drostanolone capronate) azine or 2α-methyl-5α-androstan-17β-ol-3-one 17β-hexanoate azine, is a synthetic, injected androgen/anabolic steroid (AAS) and derivative of dihydrotestosterone (DHT). It is an androgen ester – specifically, the C17β hexanoate ester of bolazine.

Boldenone undecylenate, or boldenone undecenoate, sold under the brand names Equipoise and Parenabol among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, mainly in horses. It was formerly used in humans as well. It is given by injection into muscle.

Clostebol acetate (BAN), also known as 4-chlorotestosterone 17β-acetate (4-CLTA) or as 4-chloroandrost-4-en-17β-ol-3-one 17β-acetate, is a synthetic, injected anabolic-androgenic steroid (AAS) and a derivative of testosterone that is marketed in Germany and Italy. It is an androgen ester – specifically, the C17β acetate ester of clostebol (4-chlorotestosterone) – and acts as a prodrug of clostebol in the body. Clostebol acetate is administered via intramuscular injection.

Clostebol caproate, also known as clostebol hexanoate or chlorotestosterone caproate (JAN), as well as 4-chlorotestosterone 17β-caproate or as 4-chloroandrost-4-en-17β-ol-3-one 17β-caproate, is a synthetic, injected anabolic-androgenic steroid (AAS) and a derivative of testosterone. It is an androgen ester – specifically, the C17β caproate ester of clostebol (4-chlorotestosterone) – and acts as a prodrug of clostebol in the body. Clostebol acetate is administered via intramuscular injection.

Clostebol propionate, also known as 4-chlorotestosterone 17β-propionate or as 4-chloroandrost-4-en-17β-ol-3-one 17β-propionate, is a synthetic, injected anabolic-androgenic steroid (AAS) and a derivative of testosterone. It is an androgen ester – specifically, the C17β propionate ester of clostebol (4-chlorotestosterone) – and acts as a prodrug of clostebol in the body. Clostebol acetate is administered via intramuscular injection.

Dehydroepiandrosterone sulfate, abbreviated as DHEA sulfate or DHEA-S, also known as androstenolone sulfate, is an endogenous androstane steroid that is produced by the adrenal cortex. It is the 3β-sulfate ester and a metabolite of dehydroepiandrosterone (DHEA) that circulates in far greater relative concentrations. The steroid is hormonally inert and is instead an important neurosteroid and neurotrophin.

Dimethandrolone buciclate, or dimethandrolone bucyclate, also known as 7α,11β-dimethyl-19-nortestosterone 17β-buciclate, is a synthetic anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time. It is an androgen ester – specifically, the C17β buciclate (4-butylcyclohexane-1-carboxylate) ester of dimethandrolone (7α,11β-dimethyl-19-nortestosterone) – and acts as a prodrug of dimethandrolone in the body. Dimethandrolone buciclate is or was under investigation as a potential male contraceptive.

Dimethandrolone dodecylcarbonate, or dimethandrolone dodecanoylcarbonate, also known as 7α,11β-dimethyl-19-nortestosterone 17β-dodecylcarbonate, is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time. It is an androgen ester – specifically, the C17β dodecylcarbonate ester of dimethandrolone (7α,11β-dimethyl-19-nortestosterone) – and acts as a prodrug of dimethandrolone in the body.

Dimethandrolone undecanoate (DMAU), also known by its developmental code name CDB-4521, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under development as a potential birth control pill for men. It is taken by mouth, but can also be given by injection into muscle.

Drostanolone propionate, or dromostanolone propionate, sold under the brand names Drolban, Masteril, and Masteron among others, is an androgen and anabolic steroid (AAS) medication which was used to treat breast cancer in women but is now no longer marketed. It is given by injection into muscle.

This is a list of androgen esters, including esters of natural androgens like testosterone and dihydrotestosterone (DHT) and synthetic anabolic–androgenic steroids (AAS) like nandrolone (19-nortestosterone).

Mesterolone cipionate is a synthetic anabolic–androgenic steroid and an androgen ester – specifically, the C17β cypionate ester of mesterolone – which was never marketed. It is administered via intramuscular injection once every two weeks and acts as a long-acting prodrug of mesterolone. The drug was studied in the treatment of depression in men along with mesterolone in the mid-1970s but was never introduced for medical use.

Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is taken by mouth. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. A related drug, metenolone enanthate, is given by injection into muscle.

Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is given by injection into muscle. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market. A related drug, metenolone acetate, is taken by mouth.

Methandriol diacetate, or methylandrostenediol diacetate, also known as 17α-methylandrost-5-ene-3β,17β-diol 3β,17β-diacetate, is a synthetic, injected anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of 5-androstenediol that was never marketed. It is an androgen ester – specifically, the C3,17β diacetate ester of methandriol (17α-methyl-5-androstenediol) – and acts as a prodrug of methandriol in the body.

Methandriol dipropionate (MADP), also known as methylandrostenediol dipropionate and sold under the brand names Arbolic, Durabolic, Or-Bolic, Probolik, and Protabolin among others, is a synthetic, injected anabolic-androgenic steroid (AAS) and a 17α-alkylated derivative of 5-androstenediol. It is an androgen ester – specifically, the C3,17β dipropionate ester of methandriol (17α-methyl-5-androstenediol) – and acts as a prodrug of methandriol in the body. Methandriol dipropionate is administered by intramuscular injection and, relative to methandriol, has an extended duration via this route of several days due to a depot effect afforded by its ester. It was marketed in the United States, but is no longer available in this country.

Methandriol propionate, or methylandrostenediol propionate, also known as 17α-methylandrost-5-ene-3β,17β-diol 3β-propionate, is a synthetic, injected anabolic-androgenic steroid (AAS) and a 17α-alkylated derivative of 5-androstenediol that is or was marketed by Vister in Italy. It is an androgen ester – specifically, the C3,17β propionate ester of methandriol (17α-methyl-5-androstenediol) – and acts as a prodrug of methandriol in the body. Methandriol propionate is administered by intramuscular injection and, relative to methandriol, has an extended duration via this route due to a depot effect afforded by its ester.

11β-Methyl-19-nortestosterone 17β-dodecylcarbonate (11β-MNTDC) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed for medical use at this time. It is an androgen ester – specifically, the C17β dodecylcarbonate ester of 11β-methyl-19-nortestosterone (11β-MNT) – and acts as a prodrug of 11β-MNT in the body.

Nisterime acetate (USAN), also known as 2α-chloro-4,5α-dihydrotestosterone O-(p-nitrophenyl)oxime 17β-acetate or as 2α-chloro-5α-androstan-17β-ol-3-one O-(p-nitrophenyl)oxime 17β-acetate, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a derivative of dihydrotestosterone (DHT) that was developed as a postcoital contraceptive but was never marketed. It is an androgen ester – specifically, the C17α acetate ester of nisterime. Unlike antiprogestogens like mifepristone, nisterime acetate does not prevent implantation and instead induces embryo resorption as well as interrupts the post-implantation stage of pregnancy.

Norclostebol acetate, or norchlorotestosterone acetate (NClTA), also known as 4-chloro-19-nortestosterone 17β-acetate or as 4-chloroestr-4-en-17β-ol-3-one, is a synthetic, injectable anabolic-androgenic steroid (AAS) and derivative of 19-nortestosterone (nandrolone). It is an androgen ester – specifically, the C17β acetate ester of norclostebol (4-chloro-19-nortestosterone).

Oxabolone cipionate, or oxabolone cypionate, also known as 4-hydroxy-19-nortestosterone 17β-cypionate or estr-4-en-4,17β-diol-3-one 17β-cypionate, is synthetic and injected anabolic–androgenic steroid (AAS) and derivative of nandrolone (19-nortestosterone) which has been marketed in Europe. It is the C17β cypionate ester and a prodrug of oxabolone (4-hydroxy-19-nortestosterone).

Prasterone enanthate, also known as dehydroepiandrosterone enanthate (DHEA-E) and sold in combination with estradiol valerate under the brand name Gynodian Depot among others, is a weak androgen, estrogen, and neurosteroid medication which is used as a component of menopausal hormone therapy to treat menopausal symptoms in women. It is available only as an injectable preparation in combination with estradiol valerate. The medication is given by injection into muscle typically once ever 4 weeks.

Prasterone sulfate, also known as dehydroepiandrosterone sulfate (DHEA-S), is a naturally occurring androstane steroid which is marketed and used in Japan and other countries as a labor inducer in the treatment of insufficient cervical ripening and dilation during childbirth. It is the C3β sulfate ester of prasterone, and is known to act as a prohormone of DHEA and by extension of androgens and estrogens, although it also has its own activity as a neurosteroid. Prasterone sulfate is used medically as the sodium salt via injection and is referred to by the name sodium prasterone sulfate (JAN).

Propetandrol (INN), or propethandrol, also known as 17α-ethyl-19-nortestosterone 3β-propionate or 17α-ethyl-19-nor-4-androstenediol 3β-propionate, as well as 17α-ethylestr-4-en-3β,17β-diol 3β-propionate, is a synthetic and orally active anabolic–androgenic steroid (AAS) and progestogen and a 17α-alkylated derivative of 19-nortestosterone. It is an androgen ester – specifically, the 3β-propionate ester of norethandrolone (17α-ethyl-19-nortestosterone).

Stenbolone acetate (USAN), also known as 2-methyl-4,5α-dihydro-δ1-testosterone 17β-acetate or as 2-methyl-5α-androst-1-en-17β-ol-3-one 17β-acetate, is a synthetic, injected anabolic–androgenic steroid (AAS) and derivative of dihydrotestosterone (DHT) which has been marketed in Spain. It is the C17β acetate ester of stenbolone, which is structurally related to 1-testosterone and to drostanolone (2α-methyl-DHT).

Trenbolone acetate, sold under brand names such as Finajet and Finaplix among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, specifically to increase the profitability of livestock by promoting muscle growth in cattle. It is given by injection into muscle.

Trenbolone enanthate, known by the nickname Trenabol, is a synthetic and injected anabolic–androgenic steroid (AAS) and a derivative of nandrolone which was never marketed. It is the C17β enanthate ester and a long-acting prodrug of trenbolone. Trenbolone enanthate was never approved for medical or veterinary use but is used in scientific research and has been sold on the internet black market as a designer steroid for bodybuilders and athletes.

Trenbolone hexahydrobenzylcarbonate, or trenbolone cyclohexylmethylcarbonate, sold under the brand names Parabolan and Hexabolan, is a synthetic, injected anabolic–androgenic steroid (AAS) of the nandrolone group and an androgen ester – specifically, the C17β hexahydrobenzylcarbonate (cyclohexylmethylcarbonate) ester of trenbolone – which was marketed in France for medical use in humans but has since been discontinued.

Trenbolone undecanoate, or trenbolone undecylate, is a synthetic and injected anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was never marketed. It is the C17β undecanoate (undecylate) ester and a long-acting prodrug of trenbolone. The drug was described by Roussel Uclaf in 1967 and was the first long-lasting ester of trenbolone to be developed. Subsequently, trenbolone hexahydrobenzylcarbonate, a roughly equivalent compound, was developed and introduced for use in humans in 1980, though it was discontinued in 1997. Trenbolone enanthate is another long-lasting ester of trenbolone. Similarly to trenbolone undecanoate, it was never marketed, but it has been sold on the black market as a designer steroid for bodybuilders and athletes.

Trestolone acetate is a synthetic and injected anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was never marketed. It is an androgen ester – specifically, the C17 acetate ester of trestolone. The medication was first described in 1963.

Trestolone enanthate, also known as 7α-methyl-19-nortestosterone 17β-enanthate, is an androgen and anabolic steroid (AAS) and progestogen which was never marketed. It is an androgen ester; specifically, it is the C17β enanthate (heptanoate) ester of trestolone (7α-methylestr-4-en-17β-ol-3-one). Trestolone enanthate has low affinity for sex hormone-binding globulin (SHBG), similarly to testosterone enanthate.