Dihydrotestosterone Ester
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androgen ester 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-res ...
s, including
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 ...
s (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
natural Nature is an inherent character or constitution, particularly of the ecosphere or the universe as a whole. In this general sense nature refers to the laws, elements and phenomena of the physical world, including life. Although humans are part ...
androgen An androgen (from Greek ''andr-'', the stem of the word meaning ) is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This includes ...
s like
testosterone Testosterone is the primary male sex hormone and androgen in Male, males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testicles and prostate, as well as promoting se ...
and
dihydrotestosterone Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production o ...
(DHT) and
synthetic Synthetic may refer to: Science * Synthetic biology * Synthetic chemical or compound, produced by the process of chemical synthesis * Synthetic elements, chemical elements that are not naturally found on Earth and therefore have to be created in ...
anabolic–androgenic steroid Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to testosterone, the main male sex hormone, and produce effects by binding to the androgen receptor (AR). Anabolism, Anaboli ...
s (AAS) like
nandrolone Nandrolone, also known as 19-nortestosterone, is an endogenous androgen. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate ...
(19-nortestosterone).


Esters of natural AAS


Testosterone esters


Marketed

Many esters of testosterone have been marketed, including the following major esters: * Testosterone caproate (component of Omnadren and Triormon Depositum) * Testosterone cypionate (Depo-Testosterone, numerous others) * Testosterone decanoate (component of Sustanon 250) *
Testosterone enanthate Testosterone enanthate is used in the treatment of low testosterone levels in men. It is also used in hormone therapy for women and transgender men. It is given by injection into muscle or subcutaneously usually once every one to four weeks. ...
(Delatestryl, numerous others) (component of Testoviron Depot) * Testosterone isobutyrate (Agovirin-Depot, Perandren M, Testocryst, Virex-Cryst; component of Femandren M/Folivirin) *
Testosterone isocaproate Testosterone isocaproate (; TiCa), sold under the brand names Sustanon 100, Sustanon 250, and Omnadren 250, is an androgen and anabolic steroid medication and a testosterone ester This is a list of androgen esters, including esters (as well ...
(component of Omnadren,
Sustanon 100 Testosterone propionate/testosterone phenylpropionate/testosterone isocaproate (TP/TPP/TiC), sold under the brand name Sustanon 100 (Organon), is an injectable combination medication of three testosterone esters, all of which are androgens/anabo ...
, and Sustanon 250) *
Testosterone phenylpropionate Testosterone phenylpropionate (; TPP) (brand name Testolent), or testosterone phenpropionate, also known as testosterone hydrocinnamate, is a synthetic anabolic-androgenic steroid (AAS) and an androgen ester – specifically, the C17β phenyl ...
(component of Omnadren,
Sustanon 100 Testosterone propionate/testosterone phenylpropionate/testosterone isocaproate (TP/TPP/TiC), sold under the brand name Sustanon 100 (Organon), is an injectable combination medication of three testosterone esters, all of which are androgens/anabo ...
, and Sustanon 250) *
Testosterone propionate Testosterone propionate, sold under the brand name Testoviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It has also been used to treat breast cance ...
(Testoviron, numerous others) (component of Omnadren,
Sustanon 100 Testosterone propionate/testosterone phenylpropionate/testosterone isocaproate (TP/TPP/TiC), sold under the brand name Sustanon 100 (Organon), is an injectable combination medication of three testosterone esters, all of which are androgens/anabo ...
, Sustanon 250, and Testoviron Depot) *
Testosterone undecanoate Testosterone undecanoate, sold under the brand name Nebido among others, is an androgen and anabolic steroid (AAS) medication that is used mainly in the treatment of low testosterone levels in men, It is taken by mouth or given by injection ...
(Aveed, Andriol, Nebido, Jatenzo, numerous others) And the following less commonly used esters: *
Testosterone acetate Testosterone acetate (brand names Aceto-Sterandryl, Aceto-Testoviron, Amolisin, Androtest A, Deposteron, Farmatest, Perandrone A), or testosterone ethanoate, also known as androst-4-en-17β-ol-3-one 17β-acetate, is an androgen and anabolic stero ...
(Aceto-Sterandryl, Aceto-Testoviron, Amolisin, Androtest A, Deposteron, Farmatest, Perandrone A) *
Testosterone cyclohexylpropionate Testosterone cyclohexylpropionate (TCHP; brand names Andromar, Femolone, Telipex Retard) is an androgen and anabolic steroid and a testosterone ester This is a list of androgen esters, including esters (as well as ethers) of natural androge ...
(Andromar, Femolone, Telipex Retard; component of
Trioestrine Retard Estradiol diundecylate/hydroxyprogesterone heptanoate/testosterone cyclohexylpropionate (EDU/OHPH/TCHP), sold under the brand name Trioestrine Retard, is an injectable combination medication of estradiol diundecylate (EDU), an estrogen, hydrox ...
) *
Testosterone enantate benzilic acid hydrazone Testosterone enantate benzilic acid hydrazone (TEBH), or testosterone 17β-enantate 3-benzilic acid hydrazone, is a synthetic, injected androgen/anabolic steroid and an androgen ester – specifically, the C17β enantate ( heptanoate) ester an ...
(component of
Climacteron Estradiol benzoate/estradiol dienanthate/testosterone enanthate benzilic acid hydrazone (EB/EDE/TEBH), sold under the brand names Climacteron, Lactimex, Lactostat, and Amenose, is an injectable combination medication of estradiol benzoate (EB) ...
) * Testosterone furoate (Furotest) * Testosterone hexahydrobenzoate (Sterandryl Retard; component of Trinestril AP) * Testosterone hexahydrobenzylcarbonate (Lontanyl) * Testosterone hexyloxyphenylpropionate (Andradurin) * Testosterone ketolaurate (Androdurin; component of Testosid-Depot and Klimanosid R-Depot) * Testosterone nicotinate (Bolfortan, Linobol) * Testosterone phenylacetate (Perandren, Androject) *
Testosterone phosphate Testosterone phosphate (brand name Telipex Aquosum) is an androgen and anabolic steroid and a testosterone ester. Its structure A structure is an arrangement and organization of interrelated elements in a material object or system, or the obj ...
(Telipex Aquosum) *
Testosterone undecylenate Testosterone undecylenate (TUe) is an androgen/anabolic steroid medication and androgen ester which is no longer marketed. It was a component of Durasteron and Triolandren, long-acting combination drug, mixtures of testosterone esters in oil solu ...
(component of Durasteron and Triolandren) * Testosterone valerate (component of Deposterona and Triolandren)


Never marketed

The following major testosterone ester has not been marketed: * Testosterone buciclate (20 Aet-1, CDB-1781) – a very long-acting testosterone ester that was under development but ultimately did not reach the market And the following less commonly known testosterone esters have also not been marketed: *
Polytestosterone phloretin phosphate Polytestosterone phloretin phosphate (PTPP) is an androgen and anabolic steroid as well as androgen ester which was never marketed. It is an ester of testosterone with phosphoric acid that is in the form of a polymer and is coupled with phloret ...
* Testosterone 17β-(1-((5-(aminosulfonyl)-2-pyridinyl)carbonyl)--proline) (EC586) * Testosterone acetate butyrate * Testosterone acetate propionate * Testosterone benzoate * Testosterone butyrate * Testosterone diacetate * Testosterone dipropionate * Testosterone formate * Testosterone isovalerate * Testosterone palmitate * Testosterone phenylbutyrate * Testosterone stearate * Testosterone succinate * Testosterone sulfate


Dihydrotestosterone esters


Marketed

Several esters of
dihydrotestosterone Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production o ...
(DHT; androstanolone, stanolone) have also been marketed, including the following: * Androstanolone benzoate (Ermalone-Amp, Hermalone, Sarcosan) * Androstanolone enanthate (Anaboleen Depot) * Androstanolone propionate (Pesomax) * Androstanolone valerate (Apeton)


Never marketed

The following esters of DHT have not been marketed: * Dihydrotestosterone acetate * Dihydrotestosterone butyrate * Dihydrotestosterone formate * Dihydrotestosterone undecanoate Testifenon (chlorphenacyl DHT ester) is a
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 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 ...
of DHT that was developed as a cytostatic antineoplastic agent but was never marketed.


Esters of other natural AAS


Marketed

The following esters of other natural AAS have been marketed: * Androstenediol dipropionate (Bisexovister, Bisexovis, Ginandrin, Stenandiol) * Prasterone enantate (DHEA enantate) (Gynodian Depot (in combination with
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 ...
)) *
Prasterone sulfate Prasterone sulfate (brand names Astenile, Mylis, Teloin, others), 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 t ...
(DHEA sulfate) (Astenile, Mylis, Teloin)


Never marketed

And the following have not been marketed: *
Androstenediol 3β-acetate 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 ( ...
* Androstenediol 3β-acetate 17β-benzoate * Androstenediol 17β-acetate * Androstenediol diacetate Sturamustine is a
nitrosourea Nitrosourea is both the name of a molecule, and a class of compounds that include a nitroso (R-NO) group and a urea. Examples Examples include: * Arabinopyranosyl-''N''-methyl-''N''-nitrosourea (Aranose) * Carmustine (BCNU, BiCNU) * Chlorozo ...
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 ...
of
dehydroepiandrosterone Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. It is one of the most abundant circulating steroids in humans. DHEA is produced in the adrenal glands, the gonads, and the brain. It funct ...
(DHEA) that was developed as a cytostatic antineoplastic agent but was never marketed.


Ethers of natural AAS


Marketed

Although not esters, the following ethers of natural AAS have been marketed as well: * Cloxotestosterone acetate (Caprosem) – the 17-O-chloral
hemiacetal In organic chemistry, a hemiacetal is a functional group the general formula , where is a hydrogen atom or an organic substituent. They generally result from the nucleophilic Addition reaction, addition of an Alcohol (chemistry), alcohol (a compo ...
acetate An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic, or radical base). "Acetate" also describes the conjugate base or ion (specifically, the negatively charged ion called ...
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†...
of testosterone


Never marketed

And the following have not been marketed: * Cloxotestosterone – the 17-O-chloral
hemiacetal In organic chemistry, a hemiacetal is a functional group the general formula , where is a hydrogen atom or an organic substituent. They generally result from the nucleophilic Addition reaction, addition of an Alcohol (chemistry), alcohol (a compo ...
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†...
of testosterone * Silandrone (SC-16148) – the 17-O-trimethylsilyl ether of testosterone


Esters of synthetic AAS


Methandriol esters


Marketed

*
Methandriol bisenanthoyl acetate Methandriol bisenanthoyl acetate (brand name Notandron-Depot), or methylandrostenediol bisenanthoyl acetate, also known as 17α-methylandrost-5-ene-3β,17β-diol 3β,17β-di(3-oxononanoate), is a synthetic, injected anabolic–androgenic steroid ...
(Notandron-Depot) *
Methandriol dipropionate 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 ...
(Arbolic, Durabolic, Or-Bolic, Probolik, Protabolin) *
Methandriol propionate Methandriol propionate (brand name Metilbisexovis), 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 derivat ...
(Metilbisexovis)


Never marketed

*
Methandriol diacetate Methandriol diacetate, or methylandrostenediol diacetate, also known as 17α-methylandrost-5-ene-3β,17β-diol 3β,17β-diacetate, is a synthetic compound, synthetic, injection (medicine), injected anabolic–androgenic steroid (AAS) and a 17α-a ...


Nandrolone esters


Marketed

Many esters of the synthetic AAS
nandrolone Nandrolone, also known as 19-nortestosterone, is an endogenous androgen. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate ...
(19-nortestosterone) have been marketed, including the following major esters: * Nandrolone decanoate (Deca-Durabolin, others) * Nandrolone phenylpropionate (Durabolin, others) And the following less commonly used esters: * Nandrolone caproate (Anabolin Depot) * Nandrolone cyclohexanecarboxylate (Nor-Durandron, Norlongandron) * Nandrolone cyclohexylpropionate (Andol, Fherbolico, Megabolin, Megabolin Retar, Pluropon, Proteron-Depot, Sanabolicum) * Nandrolone cypionate (Anabo, Depo-Nortestonate, Dynabol, Nortestrionate, Pluropon, Sterocrinolo) * Nandrolone furylpropionate (Demelon) *
Nandrolone hexyloxyphenylpropionate Nandrolone hexyloxyphenylpropionate (NHPP; brand names Anador, Anadur, Anadurine), also known as 19-nortestosterone 17β-(3-(4-hexyloxy)phenyl)propionate, is a synthetic compound, synthetic androgen and anabolic steroid and a nandrolone ester tha ...
(Anador, Anadur, Anadurine) * Nandrolone hydrogen succinate (Anabolico, Menidrabol) * Nandrolone laurate (Clinibolin, Fortadex, Laurabolin) * Nandrolone propionate (Anabolicus, Nor-Anabol, Nortesto, Norbyol 19, Pondus, Testobolin) * Nandrolone sulfate (Keratyl, Nandrol, Nandain, Colirio Ocul Nandrol) * Nandrolone undecanoate (Dynabolin, Dynabolon, Psychobolan)


Never marketed

The following nandrolone esters exist but were never marketed: * Bolmantalate (nandrolone 17β-adamantoate) * Nandrolone acetate * Nandrolone benzoate * Nandrolone cyclotate * Nandrolone enanthate * Nandrolone formate * Nandrolone nonanoate LS-1727 is a nitroso
carbamate In organic chemistry, a carbamate is a category of organic compounds with the general Chemical formula, formula and Chemical structure, structure , which are formally Derivative (chemistry), derived from carbamic acid (). The term includes orga ...
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 ...
of nandrolone that was developed as a cytostatic antineoplastic agent but was never marketed.


Trenbolone esters


Marketed

A few esters of the synthetic AAS
trenbolone Trenbolone is an androgen and anabolic steroid (AAS) of the nandrolone group which itself was never marketed. Trenbolone ester prodrugs, including trenbolone acetate (brand names Finajet, Finaplix, others) and trenbolone hexahydrobenzylcarbonat ...
have been marketed, including the following esters: *
Trenbolone acetate Trenbolone acetate, sold under brand names such as Finajet and Finaplix among others, is an androgen and anabolic steroid (AAS) medication used in veterinary medicine, specifically to increase the profitability of livestock by promoting muscle g ...
(Revalor, Finaplix, Finajet) * Trenbolone hexahydrobenzylcarbonate (Parabolan, Hexabolan)


Never marketed

The following trenbolone esters exist but were never marketed: * Trenbolone enanthate * Trenbolone undecanoate


Esters of other synthetic AAS


Marketed

Many esters of other synthetic AAS have been marketed as well, including the following: *
Bolandiol dipropionate Bolandiol dipropionate (USAN; brand names Anabiol, Storinal; former development code SC-7525; also known as bolandiol propionate ( JAN), norpropandrolate, 19-nor-4-androstenediol dipropionate, or estr-4-ene-3β,17β-diol 3,17-dipropionate) is a s ...
(Anabiol, Storinal) * Bolazine capronate (bolazine caproate) (Roxilon Inject) * Boldenone acetate (Equilon 100) * Boldenone cypionate (Equilon 100) * Boldenone propionate (Equilon 100) *
Boldenone undecylenate 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 ...
(boldenone undecenoate) (Boldane, Equilon 100, Equipoise, Parenabol, Vebonol, others) * Clostebol acetate (Macrobin, Steranabol, Alfa-Trofodermin, Megagrisevit) * Clostebol caproate (Macrobin-Depot) * Clostebol propionate (Yonchlon) * Drostanolone propionate (Masteron, Drolban, Masteril, Mastisol, Metormon, Permastril) * Metenolone acetate (Primobolan, Primobolan S, Primonabol, Nibal) * Metenolone enantate (Primobolan Depot) * Norclostebol acetate (Anabol 4-19) * Oxabolone cipionate (Steranabol Depo, Steranabol Ritardo) * Propetandrol (norethandrolone 3β-propionate) (Solevar) * Stenbolone acetate (Stenobolone, Anatrofin)


Never marketed

Whereas the following have not been marketed: * 11β-Methyl-19-nortestosterone dodecylcarbonate * Dimethandrolone buciclate * Dimethandrolone dodecylcarbonate *
Dimethandrolone undecanoate 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 tak ...
* Mesterolone cypionate * Nisterime acetate * Trestolone acetate * Trestolone enantate


Ethers of synthetic AAS


Marketed

Although not esters, the following ethers of synthetic AAS have been marketed as well: *
Mepitiostane Mepitiostane, sold under the brand name Thioderon, is an orally active antiestrogen and anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which is marketed in Japan as an antineoplastic agent for the treatment of breas ...
(Thioderon) – 17β-(1-methyloxycyclopentyl) ether of
epitiostanol Epitiostanol, sold under the brand name Thiodrol, is an injected antiestrogen and anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was described in the literature in 1965 and has been marketed in Japan as an an ...
* Methyltestosterone 3-hexyl ether (Androgenol, Enoltestovis, Enoltestovister) – 3-hexyl enol ether of
methyltestosterone Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low ...
* Penmesterol (penmestrol) (Pandrocine, Testopan) – 3-cyclopentyl enol ether of
methyltestosterone Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low ...
* Quinbolone (Anabolicum, Anabolvis) – 17β-cyclopentenyl enol ether of
boldenone Boldenone (developmental code name RU-18761), is a naturally occurring anabolic–androgenic steroid (AAS) and the 1(2)- dehydrogenated analogue of testosterone. Boldenone itself has never been marketed; as a pharmaceutical drug, it is used as ...
(Δ1-testosterone)


Never marketed

And the following have not been marketed: *
Mesabolone Mesabolone, also known as 1-testosterone 17β-methoxycyclopentyl ether, is a synthetic anabolic–androgenic steroid (AAS) that was never marketed. It is the 17β-(1-methoxycyclohexane) ether In organic chemistry, ethers are a class of compo ...
– 17β-(1-methyloxycyclohexyl) ether of 1-testosterone (dihydroboldenone) * Methoxydienone (methoxygonadiene) – 3-methyl ether of 17-dehydro-18-methyl-19-nor-δ2,5(10)-testosterone *
Prostanozol Prostanozol, also known as demethylstanozolol tetrahydropyran ether, is an androgen/anabolic steroid (AAS) and designer steroid which acts as a prodrug of the 17α-demethylated analogue of stanozolol (Winstrol). It was found in 2005 as an ingre ...
– 17β-tetrahydropyran ether of the 17α-demethylated analogue of
stanozolol Stanozolol (Abbreviation, abbrev. Stz), sold under many brand names, is a synthetic androgen and anabolic steroid (AAS) medication derived from dihydrotestosterone (DHT). It is used to treat hereditary angioedema. It was developed by American ph ...


See also

* List of androgens/anabolic steroids * List of estrogen esters * List of progestogen esters * List of corticosteroid esters


References

{{Androgen receptor modulators Androgen esters Anabolic–androgenic steroids Sex hormone esters and conjugates