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).
Esters of natural AAS
[edit]Testosterone esters
[edit]Marketed
[edit]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
[edit]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
Dihydrotestosterone esters
[edit]Marketed
[edit]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
[edit]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]
Esters of other natural AAS
[edit]Marketed
[edit]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
[edit]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]
Ethers of natural AAS
[edit]Marketed
[edit]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[2]
Never marketed
[edit]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
[edit]Methandriol esters
[edit]Marketed
[edit]- Methandriol bisenanthoyl acetate (Notandron-Depot)
- Methandriol dipropionate (Arbolic, Durabolic, Or-Bolic, Probolik, Protabolin)
- Methandriol propionate (Metilbisexovis)
Never marketed
[edit]Nandrolone esters
[edit]Marketed
[edit]Many esters of the synthetic AAS nandrolone (19-nortestosterone) have been marketed, including the following major esters:[14][15][16]
- Nandrolone decanoate (Deca-Durabolin, others)
- Nandrolone phenylpropionate (Durabolin, others)
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
[edit]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]
Trenbolone esters
[edit]Marketed
[edit]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
[edit]The following trenbolone esters exist but were never marketed:
Esters of other synthetic AAS
[edit]Marketed
[edit]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
[edit]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
[edit]Marketed
[edit]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
[edit]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
[edit]- List of androgens/anabolic steroids
- List of estrogen esters
- List of progestogen esters
- List of corticosteroid esters
References
[edit]- ^ a b c d Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. ISBN 978-3-88763-075-1. Retrieved 29 May 2012.
- ^ a b c d e f g 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.
- ^ William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 437–. ISBN 978-0-9828280-1-4.
- ^ E. Nieschlag; H. M. Behre (1 April 2004). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 692–. ISBN 978-1-139-45221-2.
- ^ 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.
- ^ "R&D Research". www.evestra.com. Archived from the original on 2017-09-29.
- ^ 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.
- ^ a b 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.
- ^ a b 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.
- ^ 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.
- ^ George W.A Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 67–. ISBN 978-1-351-78989-9.
- ^ 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.
- ^ 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.
- ^ a b 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.
- ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–717. ISBN 978-3-88763-075-1.
- ^ a b 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.
- ^ 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.
- ^ 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.
- ^ 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.