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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:

• 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:

• 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)

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
• Testosterone 17β-(1-((5-(aminosulfonyl)-2-pyridinyl)carbonyl)-L-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 (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 ester 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))
• Prasterone sulfate (DHEA sulfate) (Astenile, Mylis, Teloin)

Never marketed

And the following have not been marketed:

• Androstenediol 3β-acetate
• Androstenediol 3β-acetate 17β-benzoate
• 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.

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

Never marketed

And the following have not been marketed:

• Cloxotestosterone – the 17-O-chloral hemiacetal ether of testosterone
• Silandrone (SC-16148) – the 17-O-trimethylsilyl ether of testosterone

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:

• 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 (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 nitrosocarbamate ester 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 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-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-testosterone
• Prostanozol – 17β-tetrahydropyran ether of the 17α-demethylated analogue of stanozolol

See also

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

References

1. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. ISBN 978-3-88763-075-1. Retrieved 29 May 2012.
2. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 642–. ISBN 978-1-4757-2085-3.
3. William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 437–. ISBN 978-0-9828280-1-4.
4. E. Nieschlag; H. M. Behre (1 April 2004). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 692–. ISBN 978-1-139-45221-2.
5. Shalender Bhasin (13 February 1996). Pharmacology, Biology, and Clinical Applications of Androgens: Current Status and Future Prospects. John Wiley & Sons. pp. 471–. ISBN 978-0-471-13320-9.
6. "R&D Research". www.evestra.com. Archived from the original on 2017-09-29.
7. Ahmed G, Elger W, Meece F, Nair HB, Schneider B, Wyrwa R, Nickisch K (October 2017). "A prodrug design for improved oral absorption and reduced hepatic interaction". Bioorg. Med. Chem. 25 (20): 5569–5575. doi:10.1016/j.bmc.2017.08.027. PMID 28886996.
8. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 640–. ISBN 978-1-4757-2085-3.
9. ^ I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 261–. ISBN 978-94-011-4439-1.
10. Lagova ND, Sof'ina ZP, Shkodinskaia EN, Kurdiumova KN, Valueva IM (1988). "". Vopr Onkol (in Russian). 34 (11): 1363–8. PMID 3201773.
11. George W.A Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 67–. ISBN 978-1-351-78989-9.
12. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 1122. ISBN 978-1-4757-2085-3.
13. Chavis C, de Gourcy C, Borgna JL, Imbach JL (1982). "New steroidal nitrosoureas". Steroids. 39 (2): 129–47. doi:10.1016/0039-128x(82)90081-2. PMID 7071885. S2CID 21042994.
14. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 660–. ISBN 978-1-4757-2085-3.
15. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–717. ISBN 978-3-88763-075-1.
16. ^ I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-94-011-4439-1.
17. Lerner, Leonard J.; Holthaus, Fred J.; Thompson, Charles R. (1959). "A myotrophic agent and gonadotrophin inhibitor, 19-nortestosterone-17-benzoate". Endocrinology. 64 (6): 1010–1016. doi:10.1210/endo-64-6-1010. ISSN 0013-7227. PMID 13652918.
18. Boschann, H. -W. (1955). "Cytologische Untersuchungen über die Wirkung von Androgenen am atrophischen Vaginalepithel in Abhängigkeit von Dosierung und Applikationsart". Archiv für Gynäkologie. 187 (1): 39–64. doi:10.1007/BF00985845. ISSN 0003-9128. PMID 13303168. S2CID 30443548.
19. Hartley-Asp B, Wilkinson R, Venitt S, Harrap KR (1981). "Studies on the mechanism of action of LS 1727, a nitrosocarbamate of 19-nortestosterone". Acta Pharmacol Toxicol (Copenh). 48 (2): 129–38. doi:10.1111/j.1600-0773.1981.tb01598.x. PMID 6167141.

• Androgen esters
• Anabolic–androgenic steroids
• Sex hormone esters and conjugates