Androgen ester





Testosterone undecanoate, an ester of testosterone and one of the most widely used androgen esters.


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-resistant prohormones of themselves, improving oral bioavailability, increasing lipophilicity, and extending the elimination half-life (which necessitates less frequent administration). In addition, with intramuscular injection, AAS esters are absorbed more slowly into the body, further improving the elimination half-life. Aside from differences in pharmacokinetics (e.g., duration), these esters essentially have the same effects as the parent drugs.[1] They are used in androgen replacement therapy (ART), among other indications. Examples of androgen esters include testosterone esters such as testosterone cypionate, testosterone enanthate, testosterone propionate, and testosterone undecanoate and nandrolone esters such as nandrolone decanoate and nandrolone phenylpropionate.














































































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Structural properties of major testosterone esters

AndrogenStructureEster
Rel. MWb
Rel. Tc		Durationd
PositionMoietyTypeLengthaRankGroup
TestosteroneTestosteron.svg––––1.001.006Short
Testosterone propionateTestosterone propionate.svgC17βPropanoic acidStraight-chain fatty acid31.190.845Short
Testosterone cypionateTestosterone cypionate.svgC17βCyclopentylpropanoic acidAromatic fatty acid– (~6)1.430.704Moderate
Testosterone enanthateTestosterone enanthate.svgC17βHeptanoic acidStraight-chain fatty acid71.390.723Moderate
Testosterone undecanoateTestosterone undecanoate.svgC17βUndecanoic acidStraight-chain fatty acid111.580.632Long

Testosterone buciclatee		Testosteronebuciclate structure.pngC17β
Bucyclic acidf		Aromatic carboxylic acid– (~9)1.580.631Long

Footnotes: a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative molecular weight. c = Relative testosterone content by weight (i.e., relative androgenic potency). d = Duration by intramuscular or subcutaneous injection. e = Never marketed. f = Bucyclic acid = trans-4-Butylcyclohexane-1-carboxylic acid. Sources: See individual articles.






















































































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Structural properties of major anabolic steroid esters

Anabolic steroidStructureEster
Rel. MWb
Rel. AASc		Durationd
PositionMoietyTypeLengtha
Boldenone undecylenateBoldenone undecylenate.svgC17βUndecylenic acidStraight-chain fatty acid111.580.63Long
Drostanolone propionateDrostanolone propionate.svgC17βPropanoic acidStraight-chain fatty acid31.180.84Short
Metenolone acetateMetenolone acetate.svgC17βEthanoic acidStraight-chain fatty acid21.140.88Short
Metenolone enanthateMetenolone enanthate.pngC17βHeptanoic acidStraight-chain fatty acid71.370.73Long
Nandrolone decanoateNandrolone decanoate.svgC17βDecanoic acidStraight-chain fatty acid101.560.64Long
Nandrolone phenylpropionateNandrolone phenylpropionate.svgC17βPhenylpropanoic acidAromatic fatty acid– (~6–7)1.480.67Long
Trenbolone acetateTrenbolone acetate.svgC17βEthanoic acidStraight-chain fatty acid21.160.87Short

Trenbolone enanthatee		Trenbolone enanthate.svgC17βHeptanoic acidStraight-chain fatty acid71.410.71Long

Footnotes: a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative molecular weight compared to unesterified parent steroid. c = Relative anabolic steroid content by weight (i.e., relative androgenic potency) compared to unesterified parent steroid. d = Duration by intramuscular or subcutaneous injection. e = Never marketed. Sources: See individual articles.


See also


  • List of androgen esters

  • List of androgens/anabolic steroids

  • Steroid ester

  • Estrogen ester

  • Progestogen ester


References




  1. ^ Richard Lawrence Miller (2002). The Encyclopedia of Addictive Drugs. Greenwood Publishing Group. pp. 416–. ISBN 978-0-313-31807-8..mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"""""""'""'".mw-parser-output .citation .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em



Further reading



  • Vermeulen A (1975). "Longacting steroid preparations". Acta Clin Belg. 30 (1): 48–55. doi:10.1080/17843286.1975.11716973. PMID 1231448.










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