Androgen ester

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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.

Structural properties of major testosterone esters

Androgen Structure Ester Rel. MWb Rel. Tc Durationd
Position Moiety Type Lengtha Rank Group
Testosterone
Testosteron.svg
1.00 1.00 6 Short
Testosterone propionate
Testosterone propionate.svg
C17β Propanoic acid Straight-chain fatty acid 3 1.19 0.84 5 Short
Testosterone cypionate
Testosterone cypionate.svg
C17β Cyclopentylpropanoic acid Aromatic fatty acid – (~6) 1.43 0.70 4 Moderate
Testosterone enanthate
Testosterone enanthate.svg
C17β Heptanoic acid Straight-chain fatty acid 7 1.39 0.72 3 Moderate
Testosterone undecanoate
Testosterone undecanoate.svg
C17β Undecanoic acid Straight-chain fatty acid 11 1.58 0.63 2 Long
Testosterone buciclatee
Testosteronebuciclate structure.png
C17β Bucyclic acidf Aromatic carboxylic acid – (~9) 1.58 0.63 1 Long
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.

Structural properties of major anabolic steroid esters

Anabolic steroid Structure Ester Rel. MWb Rel. AASc Durationd
Position Moiety Type Lengtha
Boldenone undecylenate
Boldenone undecylenate.svg
C17β Undecylenic acid Straight-chain fatty acid 11 1.58 0.63 Long
Drostanolone propionate
Drostanolone propionate.svg
C17β Propanoic acid Straight-chain fatty acid 3 1.18 0.84 Short
Metenolone acetate
Metenolone acetate.svg
C17β Ethanoic acid Straight-chain fatty acid 2 1.14 0.88 Short
Metenolone enanthate
Metenolone enanthate.png
C17β Heptanoic acid Straight-chain fatty acid 7 1.37 0.73 Long
Nandrolone decanoate
Nandrolone decanoate.svg
C17β Decanoic acid Straight-chain fatty acid 10 1.56 0.64 Long
Nandrolone phenylpropionate
Nandrolone phenylpropionate.svg
C17β Phenylpropanoic acid Aromatic fatty acid – (~6–7) 1.48 0.67 Long
Trenbolone acetate
Trenbolone acetate.svg
C17β Ethanoic acid Straight-chain fatty acid 2 1.16 0.87 Short
Trenbolone enanthatee
Trenbolone enanthate.svg
C17β Heptanoic acid Straight-chain fatty acid 7 1.41 0.71 Long
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[edit]

References[edit]

  1. ^ Richard Lawrence Miller (2002). The Encyclopedia of Addictive Drugs. Greenwood Publishing Group. pp. 416–. ISBN 978-0-313-31807-8.

Further reading[edit]