List of androgen esters

{{Short description|None}} [[File:Testosteron.svg|thumb|right|200px|class=skin-invert-image|Testosterone, the base androgen of most 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 natural AAS== ===Testosterone esters=== ====Marketed==== Many esters of testosterone have been marketed, including the following major esters:<ref name="IndexNominum2000-1">{{cite book | title = Index Nominum 2000: International Drug Directory | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA404 | access-date = 29 May 2012 | year = 2000 | publisher = Taylor & Francis US | isbn = 978-3-88763-075-1}}</ref><ref name="Elks2014-1">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA642|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=642–}}</ref>

* Testosterone caproate (component of Omnadren and Triormon Depositum) * Testosterone cypionate (Depo-Testosterone, numerous others) * Testosterone decanoate (component of Sustanon 250) * Testosterone enanthate (Delatestryl, numerous others) (component of Testoviron Depot) * Testosterone isobutyrate (Agovirin-Depot, Perandren M, Testocryst, Virex-Cryst; component of Femandren M/Folivirin) * Testosterone isocaproate (component of Omnadren, Sustanon 100, and Sustanon 250) * Testosterone phenylpropionate (component of Omnadren, Sustanon 100, and Sustanon 250) * Testosterone propionate (Testoviron, numerous others) (component of Omnadren, Sustanon 100, Sustanon 250, and Testoviron Depot) * Testosterone undecanoate (Aveed, Andriol, Nebido, Jatenzo, numerous others)

And the following less commonly used esters:<ref name="IndexNominum2000-1" /><ref name="Elks2014-1" />

* Testosterone acetate (Aceto-Sterandryl, Aceto-Testoviron, Amolisin, Androtest A, Deposteron, Farmatest, Perandrone A) * Testosterone cyclohexylpropionate (Andromar, Femolone, Telipex Retard; component of Trioestrine Retard) * Testosterone enantate benzilic acid hydrazone (component of Climacteron) * 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 (Telipex Aquosum) * Testosterone undecylenate (component of Durasteron and Triolandren) * Testosterone valerate (component of Deposterona and Triolandren)<ref name="Llewellyn2011">{{cite book|author=William Llewellyn|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT437|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=437–}}</ref>

====Never marketed==== The following major testosterone ester has not been marketed:<ref name="IndexNominum2000-1" /><ref name="Elks2014-1" />

* Testosterone buciclate (20 Aet-1, CDB-1781) – a very long-acting testosterone ester that was under development but ultimately did not reach the market<ref name="NieschlagBehre2004">{{cite book|author1=E. Nieschlag|author2=H. M. Behre|title=Testosterone: Action, Deficiency, Substitution|url=https://books.google.com/books?id=ZiZ7MWDqo5oC&pg=PA692|date=1 April 2004|publisher=Cambridge University Press|isbn=978-1-139-45221-2|pages=692–}}</ref><ref name="Bhasin1996">{{cite book|author=Shalender Bhasin|title=Pharmacology, Biology, and Clinical Applications of Androgens: Current Status and Future Prospects|url=https://books.google.com/books?id=hurRyWje4DMC&pg=PA471|date=13 February 1996|publisher=John Wiley & Sons|isbn=978-0-471-13320-9|pages=471–}}</ref>

And the following less commonly known testosterone esters have also not been marketed:<ref name="IndexNominum2000-1" /><ref name="Elks2014-1" />

* Polytestosterone phloretin phosphate * Testosterone 17β-(1-((5-(aminosulfonyl)-2-pyridinyl)carbonyl)-{{Small|L}}-proline) (EC586)<ref name="Evestra">{{cite web |url=http://www.evestra.com/index-Dateien/Page1242.htm |title=R&D Research |website=www.evestra.com |url-status=dead |archive-url=https://web.archive.org/web/20170929164030/http://www.evestra.com/index-Dateien/Page1242.htm |archive-date=2017-09-29}} </ref><ref name="pmid28886996">{{cite journal | vauthors = Ahmed G, Elger W, Meece F, Nair HB, Schneider B, Wyrwa R, Nickisch K | title = A prodrug design for improved oral absorption and reduced hepatic interaction | journal = Bioorg. Med. Chem. | volume = 25 | issue = 20 | pages = 5569–5575 | date = October 2017 | pmid = 28886996 | doi = 10.1016/j.bmc.2017.08.027 }}</ref> * 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 (DHT; androstanolone, stanolone) have also been marketed, including the following:<ref name="Elks2014-2">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA640|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=640–}}</ref><ref name="MortonHall2012-2">{{cite book|author1=I.K. Morton|author2=Judith M. Hall|title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA261|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=261–}}</ref>

* 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:<ref name="Elks2014-2" /><ref name="MortonHall2012-2" />

* Dihydrotestosterone acetate * Dihydrotestosterone butyrate * Dihydrotestosterone formate * Dihydrotestosterone undecanoate

Testifenon (chlorphenacyl DHT ester) is a nitrogen mustard ester of DHT that was developed as a cytostatic antineoplastic agent but was never marketed.<ref name="pmid3201773">{{cite journal | vauthors = Lagova ND, Sof'ina ZP, Shkodinskaia EN, Kurdiumova KN, Valueva IM | title = [The antineoplastic activity of testiphenon] | language = ru | journal = Vopr Onkol | volume = 34 | issue = 11 | pages = 1363–8 | year = 1988 | pmid = 3201773 }}</ref>

===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)) * Prasterone sulfate (DHEA sulfate) (Astenile, Mylis, Teloin)

====Never marketed==== And the following have not been marketed:

* Androstenediol 3β-acetate * Androstenediol 3β-acetate 17β-benzoate<ref name="Milne2018">{{cite book|author=George W.A Milne|title=Drugs: Synonyms and Properties: Synonyms and Properties|url=https://books.google.com/books?id=xUlaDwAAQBAJ&pg=PT67|date=8 May 2018|publisher=Taylor & Francis|isbn=978-1-351-78989-9|pages=67–}}</ref> * Androstenediol 17β-acetate * Androstenediol diacetate

Sturamustine is a nitrosourea ester of dehydroepiandrosterone (DHEA) that was developed as a cytostatic antineoplastic agent but was never marketed.<ref name="Elks2014-4">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=RA1-PA1122|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|page=1122}}</ref><ref name="pmid7071885">{{cite journal | vauthors = Chavis C, de Gourcy C, Borgna JL, Imbach JL | title = New steroidal nitrosoureas | journal = Steroids | volume = 39 | issue = 2 | pages = 129–47 | year = 1982 | pmid = 7071885 | doi = 10.1016/0039-128x(82)90081-2| s2cid = 21042994 }}</ref>

===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 acetate ether of testosterone<ref name="Elks2014-1" />

====Never marketed==== And the following have not been marketed:

* Cloxotestosterone – the 17-O-chloral hemiacetal ether of testosterone<ref name="Elks2014-1" /> * Silandrone (SC-16148) – the 17-O-trimethylsilyl ether of testosterone<ref name="Elks2014-1" />

==Esters of synthetic AAS==

===Methandriol esters===

====Marketed==== * Methandriol bisenanthoyl acetate (Notandron-Depot) * Methandriol dipropionate (Arbolic, Durabolic, Or-Bolic, Probolik, Protabolin) * Methandriol propionate (Metilbisexovis)

====Never marketed==== * Methandriol diacetate

===Nandrolone esters===

====Marketed==== Many esters of the synthetic AAS nandrolone (19-nortestosterone) have been marketed, including the following major esters:<ref name="Elks2014-3">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA660|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=660–}}</ref><ref name="IndexNominum2000-3">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA716|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=716–717}}</ref><ref name="MortonHall2012-3">{{cite book|author1=I.K. Morton|author2=Judith M. Hall|title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA189|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1}}</ref>

* Nandrolone decanoate (Deca-Durabolin, others) * Nandrolone phenylpropionate (Durabolin, others)

And the following less commonly used esters:<ref name="Elks2014-3" /><ref name="IndexNominum2000-3" /><ref name="MortonHall2012-3" />

* 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 (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<ref name="LernerHolthaus1959">{{cite journal|last1=Lerner|first1=Leonard J.|last2=Holthaus|first2=Fred J.|last3=Thompson|first3=Charles R.|title=A myotrophic agent and gonadotrophin inhibitor, 19-nortestosterone-17-benzoate|journal=Endocrinology|volume=64|issue=6|year=1959|pages=1010–1016|issn=0013-7227|doi=10.1210/endo-64-6-1010|pmid=13652918}}</ref> * Nandrolone cyclotate * Nandrolone enanthate<ref name="Boschann1955">{{cite journal|last1=Boschann|first1=H. -W.|title=Cytologische Untersuchungen über die Wirkung von Androgenen am atrophischen Vaginalepithel in Abhängigkeit von Dosierung und Applikationsart|journal=Archiv für Gynäkologie|volume=187|issue=1|year=1955|pages=39–64|issn=0003-9128|doi=10.1007/BF00985845|pmid=13303168|s2cid=30443548 }}</ref> * Nandrolone formate * Nandrolone nonanoate

LS-1727 is a nitroso carbamate ester of nandrolone that was developed as a cytostatic antineoplastic agent but was never marketed.<ref name="pmid6167141">{{cite journal | vauthors = Hartley-Asp B, Wilkinson R, Venitt S, Harrap KR | title = Studies on the mechanism of action of LS 1727, a nitrosocarbamate of 19-nortestosterone | journal = Acta Pharmacol Toxicol (Copenh) | volume = 48 | issue = 2 | pages = 129–38 | year = 1981 | pmid = 6167141 | doi = 10.1111/j.1600-0773.1981.tb01598.x}}</ref>

===Trenbolone esters===

====Marketed==== A few esters of the synthetic AAS trenbolone have been marketed, including the following esters:

* Trenbolone acetate (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 (Anabiol, Storinal) * Bolazine capronate (bolazine caproate) (Roxilon Inject) * Boldenone acetate (Equilon 100) * Boldenone cypionate (Equilon 100) * Boldenone propionate (Equilon 100) * Boldenone undecylenate (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 * 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 (Thioderon) – 17β-(1-methyloxycyclopentyl) ether of epitiostanol * Methyltestosterone 3-hexyl ether (Androgenol, Enoltestovis, Enoltestovister) – 3-hexyl enol ether of methyltestosterone * Penmesterol (penmestrol) (Pandrocine, Testopan) – 3-cyclopentyl enol ether of methyltestosterone * Quinbolone (Anabolicum, Anabolvis) – 17β-cyclopentenyl enol ether of boldenone (Δ<sup>1</sup>-testosterone)

====Never marketed==== And the following have not been marketed:

* Mesabolone – 17β-(1-methyloxycyclohexyl) ether of 1-testosterone (dihydroboldenone) * Methoxydienone (methoxygonadiene) – 3-methyl ether of 17-dehydro-18-methyl-19-nor-δ<sup>2,5(10)</sup>-testosterone * Prostanozol – 17β-tetrahydropyran ether of the 17α-demethylated analogue of stanozolol

==References== {{Reflist}}

Category:Androgen esters Category:Androgens Category:Sex hormone esters and conjugates