Androgen ester

Multi tool use
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 |
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Position | Moiety | Type | Lengtha | Rank | Group
|
---|
Testosterone |  | – | – | – | – | 1.00 | 1.00 | 6 | Short
|
Testosterone propionate |  | C17β | Propanoic acid | Straight-chain fatty acid | 3 | 1.19 | 0.84 | 5 | Short
|
Testosterone cypionate |  | C17β | Cyclopentylpropanoic acid | Aromatic fatty acid | – (~6) | 1.43 | 0.70 | 4 | Moderate
|
Testosterone enanthate |  | C17β | Heptanoic acid | Straight-chain fatty acid | 7 | 1.39 | 0.72 | 3 | Moderate
|
Testosterone undecanoate |  | C17β | Undecanoic acid | Straight-chain fatty acid | 11 | 1.58 | 0.63 | 2 | Long
|
Testosterone buciclatee |  | 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.
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Structural properties of major anabolic steroid esters
Anabolic steroid | Structure | Ester | Rel. MWb | Rel. AASc | Durationd |
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Position | Moiety | Type | Lengtha |
---|
Boldenone undecylenate |  | C17β | Undecylenic acid | Straight-chain fatty acid | 11 | 1.58 | 0.63 | Long
|
Drostanolone propionate |  | C17β | Propanoic acid | Straight-chain fatty acid | 3 | 1.18 | 0.84 | Short
|
Metenolone acetate |  | C17β | Ethanoic acid | Straight-chain fatty acid | 2 | 1.14 | 0.88 | Short
|
Metenolone enanthate |  | C17β | Heptanoic acid | Straight-chain fatty acid | 7 | 1.37 | 0.73 | Long
|
Nandrolone decanoate |  | C17β | Decanoic acid | Straight-chain fatty acid | 10 | 1.56 | 0.64 | Long
|
Nandrolone phenylpropionate |  | C17β | Phenylpropanoic acid | Aromatic fatty acid | – (~6–7) | 1.48 | 0.67 | Long
|
Trenbolone acetate |  | C17β | Ethanoic acid | Straight-chain fatty acid | 2 | 1.16 | 0.87 | Short
|
Trenbolone enanthatee |  | 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
- List of androgen esters
- List of androgens/anabolic steroids
- Steroid ester
- Estrogen ester
- Progestogen ester
References
^ 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.
Androgens and antiandrogens
|
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Androgens (incl. AAS) |
AR agonists
| Testosterone derivatives: Androstenediol dipropionate
- Boldenone undecylenate
- Clostebol
- Clostebol acetate
- Clostebol caproate
- Clostebol propionate
- Cloxotestosterone acetate
- Prasterone (dehydroepiandrosterone, DHEA)
- Prasterone enanthate (DHEA enanthate)
- Prasterone sulfate (DHEA sulfate)
- Quinbolone
Testosterone#
Testosterone esters (e.g., testosterone cypionate, testosterone enanthate, testosterone propionate, testosterone undecanoate, testosterone ester mixtures (Deposterona, Omnadren, Sustanon, Testoviron Depot))
Dihydrotestosterone derivatives: Androstanolone (stanolone, dihydrotestosterone, DHT)
- Androstanolone esters
- Bolazine capronate
- Drostanolone propionate (dromostanolone propionate)
- Epitiostanol
- Mepitiostane
- Mesterolone
- Metenolone acetate (methenolone acetate)
- Metenolone enanthate (methenolone enanthate)
- Stenbolone acetate
19-Nortestosterone derivatives: Bolandiol dipropionate
Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate)
- Norclostebol
- Norclostebol acetate
- Oxabolone cipionate (oxabolone cypionate)
- Trenbolone acetate
- Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)
17α-Alkylated testosterone derivatives: Bolasterone
- Calusterone
- Chlorodehydromethyltestosterone (CDMT)
- Fluoxymesterone
- Formebolone
- Metandienone (methandienone, methandrostenolone)
- Methandriol (methylandrostenediol)
- Methandriol bisenanthoyl acetate
- Methandriol dipropionate
- Methandriol propionate
Methyltestosterone (+esterified estrogens)
- Methyltestosterone 3-hexyl ether
- Oxymesterone
- Penmesterol
- Tiomesterone (thiomesterone)
17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
- Furazabol
- Mebolazine (dimethazine)
- Mestanolone
- Oxandrolone
- Oxymetholone
- Stanozolol
17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol
- Mibolerone
- Norethandrolone
- Normethandrone (methylestrenolone, normethisterone)
- Propetandrol (propethandrol)
17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
17α-Ethynyltestosterone derivatives: Danazol
- Gestrinone
Progestins (e.g., ethisterone (ethynyltestosterone), levonorgestrel, norgestrel, norethisterone (norethindrone), lynestrenol, norgestrienone)
- Tibolone
Progesterone derivatives: Medroxyprogesterone acetate
|
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Progonadotropins | Antiestrogens (e.g., tamoxifen, clomifene)
GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
Gonadotropins (e.g., LH, hCG)
|
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|
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Antiandrogens |
AR antagonists
| Steroidal: Abiraterone acetate
- Canrenone
- Chlormadinone acetate
- Cyproterone acetate
- Delmadinone acetate
- Dienogest
- Drospirenone
- Medrogestone
- Megestrol acetate
- Nomegestrol acetate
- Osaterone acetate
- Oxendolone
- Potassium canrenoate
- Spironolactone
Nonsteroidal: Apalutamide
- Bicalutamide
- Cimetidine
Darolutamide†
- Enzalutamide
- Flutamide
- Ketoconazole
- Nilutamide
Seviteronel†
- Topilutamide (fluridil)
|
---|
Steroidogenesis inhibitors |
5α-Reductase | - Alfatradiol
Dutasteride (+tamsulosin)
- Epristeride
- Finasteride
- Saw palmetto extract
|
---|
Others | - Abiraterone acetate
- Aminoglutethimide
- Bifluranol
- Cyproterone acetate
- Flutamide
- Ketoconazole
- Nilutamide
Seviteronel†
- Spironolactone
|
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|
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Antigonadotropins | D2 receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
Estrogens (e.g., bifluranol, diethylstilbestrol, estradiol, estradiol esters, ethinylestradiol, ethinylestradiol sulfonate, paroxypropione)
GnRH agonists (e.g., leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Progestogens (incl., chlormadinone acetate, cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, medroxyprogesterone acetate, megestrol acetate)
|
---|
Others | Androstenedione immunogens: Androvax (androstenedione albumin)
- Ovandrotone albumin (Fecundin)
|
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|
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#WHO-EM
‡Withdrawn from market
Clinical trials:
†Phase III
§Never to phase III
- See also
- Androgen receptor modulators
- Estrogens and antiestrogens
- Progestogens and antiprogestogens
- List of androgens/anabolic steroids
|
Androgen receptor modulators
|
---|
AR |
Agonists | Testosterone derivatives: 4-Androstenediol
- 4-Dehydroepiandrosterone (4-DHEA)
- 4-Hydroxytestosterone
- 4,17α-Dimethyltestosterone
- 5-Androstenedione
- 11-Ketotestosterone
- 11β-Hydroxyandrostenedione
- Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
Androstenediol (5-androstenediol)
- Androstenediol 3β-acetate
- Androstenediol 17β-acetate
- Androstenediol diacetate
- Androstenediol dipropionate
- Androstenedione (4-androstenedione)
- Atamestane
Boldenone
- Boldione (1,4-androstadienedione)
Clostebol
- Clostebol acetate
- Clostebol caproate
- Clostebol propionate
Cloxotestosterone
- Cloxotestosterone acetate
- Dehydroandrosterone
DHEA (androstenolone, prasterone; 5-DHEA)
- DHEA enanthate (prasterone enanthate)
- DHEA sulfate
- Exemestane
- Formestane
- Plomestane
- Quinbolone
- Silandrone
Testosterone# (+dutasteride)
- Testosterone esters
- Polytestosterone phloretin phosphate
Dihydrotestosterone derivatives: 1-Androstenediol
- 1-Androstenedione
- 1-Androsterone (1-andro, 1-DHEA)
- 1-Testosterone
- 3α-Androstanediol
- 5α-Androst-2-en-17-one
- 7β-Hydroxyepiandrosterone
- 11-Ketodihydrotestosterone
- Androsterone
Bolazine
- Dihydroethisterone
- Dihydroethyltestosterone
- Dihydrofluoxymesterone
- Dihydromethylandrostenediol
Dihydrotestosterone (DHT) (androstanolone, stanolone)
- Dihydrotestosterone esters
Drostanolone
- Epiandrosterone
- Epitiostanol
- Mepitiostane
- Mesabolone
Mesterolone
- Methyldiazinol
Nisterime
- Prostanozol
Stenbolone
- Testifenon (testiphenon, testiphenone)
19-Nortestosterone derivatives: 7α-Methyl-19-norandrostenedione (MENT dione, trestione)
11β-Methyl-19-nortestosterone
- 11β-Methyl-19-nortestosterone dodecylcarbonate
- 19-Nor-5-androstenediol
- 19-Nor-5-androstenedione
- 19-Nordehydroepiandrosterone
Bolandiol
- Bolandione (19-nor-4-androstenedione)
- Bolmantalate (nandrolone adamantoate)
- Dienedione
- Dienolone
Dimethandrolone
- Dimethandrolone buciclate
- Dimethandrolone dodecylcarbonate
- Dimethandrolone undecanoate
- LS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate)
- Methoxydienone (methoxygonadiene)
Nandrolone
Norclostebol
- Normethandrone (methylestrenolone, normethisterone)
Oxabolone
- Oxabolone cipionate (oxabolone cypionate)
Trenbolone
- Trenbolone acetate
- Trenbolone enanthate
- Trenbolone hexahydrobenzylcarbonate
- Trenbolone undecanoate
- Trendione
Trestolone (MENT)
- Trestolone acetate
- Trestolone enanthate
Dihydrotestosterone and 19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
- 5α-Dihydronandrolone
- 5α-Dihydronorethandrolone
- 5α-Dihydronorethisterone
- 5α-Dihydronormethandrone
- 5α-Dihydrotrestolone
- 19-Norandrosterone
17α-Alkylated testosterone derivatives: Bolasterone
- Calusterone
- Chlorodehydromethylandrostenediol (CDMA)
- Chlorodehydromethyltestosterone (CDMT)
- Chloromethylandrostenediol (CMA)
- Enestebol
- Ethyltestosterone
- Fluoxymesterone
- Formebolone
- Hydroxystenozole
- Metandienone (methandrostenolone)
Methandriol (methylandrostenediol)
- Methandriol bisenanthoyl acetate
- Methandriol diacetate
- Methandriol dipropionate
- Methandriol propionate
- Methylclostebol (chloromethyltestosterone)
Methyltestosterone (+esterified estrogens)
- Methyltestosterone 3-hexyl ether
- Oxymesterone
- Penmesterol
- Tiomesterone
17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
- Desoxymethyltestosterone
- Furazabol
- Mebolazine (dimethazine)
- Mestanolone
Metenolone
- Metenolone acetate
- Metenolone enanthate
- Methasterone
- Methyl-1-testosterone
- Methylepitiostanol
- Methylstenbolone
- Oxandrolone
- Oxymetholone
- Stanozolol
17α-Alkylated 19-nortestosterone derivatives: Bolenol
- Dimethyldienolone
- Dimethyltrienolone
- Ethyldienolone
- Ethylestrenol
- Methyldienolone
- Methylhydroxynandrolone (MOHN, MHN)
- Metribolone
- Mibolerone
- Norboletone
- Norethandrolone
- Propetandrol
- RU-2309
- Tetrahydrogestrinone
17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
- Vinyltestosterone
17α-Ethynyltestosterone derivatives: Δ4-Tibolone
- Danazol
- Desogestrel
- Ethisterone (ethynyltestosterone)
- Etonogestrel
- Etynodiol
- Etynodiol diacetate
- Gestodene
- Gestrinone
- Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate)
- Lynestrenol
- Lynestrenol phenylpropionate
- Norethisterone
Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate)
- Norgestrel
- Norgestrienone
- Quingestanol
- Quingestanol acetate
- Tibolone
Progesterone derivatives: Medroxyprogesterone acetate
- Megestrol acetate
Others/unsorted: 3-Keto-5α-abiraterone
- 5α-Androstane
- Alternariol
- Cl-4AS-1
- Drupanol
- ZM-182345
|
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Mixed (SARMs) | Nonsteroidal: 198RL26
- ACP-105
- AC-262536
- Acetothiolutamide
- Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
- BMS-564929
- DTIB
- Enobosarm (ostarine, MK-2866, GTx-024, S-22)
- FTBU-1
- GSK-4336A
- GSK-8698
- LG-121071 (LGD-121071)
- LGD-2226
- LGD-2941 (LGD-122941)
- LGD-3303
- LGD-4033
- JNJ-26146900
- JNJ-28330835
- JNJ-37654032
- ORM-11984
- R-1
- RAD140
- RU-59063
- S-1
- S-23
- S-40503
- S-101479
- Triclosan
Steroidal: EM-9017
- MK-0773
- TFM-4AS-1
- YK-11
|
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Antagonists | |
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|
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GPRC6A |
Agonists | Cations (incl. aluminum, calcium, gadolinium, magnesium, strontium, zinc)
- Dehydroandrosterone
- Dihydrotestosterone
- Estradiol
L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine)
- Osteocalcin
- SHBG
- Testosterone
|
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|
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- See also
- Receptor/signaling modulators
- Androgens and antiandrogens
- Estrogen receptor modulators
- Progesterone receptor modulators
- List of androgens/anabolic steroids
|
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