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).

Testosterone, the base androgen of most androgen esters.

Esters of natural AAS

Marketed

Many esters of testosterone have been marketed, including the following major esters:[1][2]

  • 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:[1][2]

  • 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)[3]

Never marketed

The following major testosterone ester has not been marketed:[1][2]

  • Testosterone buciclate (20 Aet-1, CDB-1781) – a very long-acting testosterone ester that was under development but ultimately did not reach the market[4][5]

And the following less commonly known testosterone esters have also not been marketed:[1][2]

  • Polytestosterone phloretin phosphate
  • Testosterone 17β-(1-((5-(aminosulfonyl)-2-pyridinyl)carbonyl)-L-proline) (EC586)[6][7]
  • 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

Marketed

Several esters of dihydrotestosterone (DHT; androstanolone, stanolone) have also been marketed, including the following:[8][9]

  • 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:[8][9]

  • 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.[10]

Marketed

The following esters of other natural AAS have been marketed:

Never marketed

And the following have not been marketed:

  • Androstenediol 3β-acetate
  • Androstenediol 3β-acetate 17β-benzoate[11]
  • 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.[12][13]

Marketed

Although not esters, the following ethers of natural AAS have been marketed as well:

Never marketed

And the following have not been marketed:

  • Cloxotestosterone – the 17-O-chloral hemiacetal ether of testosterone[2]
  • Silandrone (SC-16148) – the 17-O-trimethylsilyl ether of testosterone[2]

Esters of synthetic AAS

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

Never marketed
  • Methandriol diacetate

Marketed

Many esters of the synthetic AAS nandrolone (19-nortestosterone) have been marketed, including the following major esters:[14][15][16]

And the following less commonly used esters:[14][15][16]

  • 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[17]
  • Nandrolone cyclotate
  • Nandrolone enanthate[18]
  • Nandrolone formate
  • Nandrolone nonanoate

LS-1727 is a nitrosocarbamate ester of nandrolone that was developed as a cytostatic antineoplastic agent but was never marketed.[19]

Marketed

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

Never marketed

The following trenbolone esters exist but were never marketed:

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

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 (Δ1-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-δ2,5(10)-testosterone
  • Prostanozol – 17β-tetrahydropyran ether of the 17α-demethylated analogue of stanozolol

See also

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). "[The antineoplastic activity of testiphenon]". 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.
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