Ethynylandrostanediol: Difference between revisions

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{{Drugbox
{{Short description|A synthetic anabolic-androgenic steroid}}
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| IUPAC_name = (3''R'',5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''R'')-17-ethynyl-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[''a'']phenanthrene-3,17-diol
| image = Ethynylandrostanediol.svg
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<!--Clinical data-->
'''Ethynylandrostanediol''' is a synthetic [[anabolic-androgenic steroid]] (AAS) that was developed in the mid-20th century. It is a derivative of [[androstanediol]], a naturally occurring [[androgen]] and [[anabolic steroid]].
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| pregnancy_US = <!-- A / B            / C / D / X -->
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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<!--Pharmacokinetic data-->
==Chemical Structure==
| bioavailability =
Ethynylandrostanediol is chemically known as 17α-ethynyl-5α-androstane-3β,17β-diol. It is a modified form of [[androstanediol]], with an ethynyl group at the 17α position. This modification is intended to enhance the compound's oral bioavailability and resistance to metabolic degradation.
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<!-- Identifiers -->
==Pharmacology==
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As an [[anabolic-androgenic steroid]], ethynylandrostanediol exhibits both [[androgenic]] and [[anabolic]] properties. It binds to [[androgen receptors]] in various tissues, promoting protein synthesis and muscle growth. The ethynyl group at the 17α position helps to prevent rapid metabolism by the liver, allowing the compound to be effective when administered orally.
| CAS_number = 183387-50-0
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| PubChem = 42611099
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| ChemSpiderID = 32698509
| UNII = 891O182ZP5
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| synonyms = HE3235; Apoptone; 17α-Ethynyl-5α-androstane-3α,17β-diol; 5α-Pregn-20-yne-3α,17α-diol


<!--Chemical data-->
==Medical Uses==
| C=21 | H=32 | O=2
Ethynylandrostanediol was initially developed for potential use in [[hormone replacement therapy]] and the treatment of conditions associated with low androgen levels. However, like many other synthetic AAS, its use in clinical practice has been limited due to concerns about side effects and the availability of safer alternatives.
| SMILES = C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C)O
| StdInChI_Ref =
| StdInChI = 1S/C21H32O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,14-18,22-23H,5-13H2,2-3H3/t14-,15+,16+,17-,18-,19-,20-,21-/m0/s1
| StdInChIKey_Ref =
| StdInChIKey = CKAXZOYFIHQCBN-JRRMKBMNSA-N
}}


'''Ethynylandrostanediol''' (developmental code name '''HE-3235'''), or '''17α-ethynyl-5α-androstane-3α,17β-diol''', also known as '''Apoptone''', is a [[synthetic compound|synthetic]], [[oral administration|orally active]], 17α-substituted [[structural analog|analogue]] of the [[androstanediol]]s which was under development for the treatment of [[prostate cancer]] and [[breast cancer]] but was discontinued.<ref name="pmid20814732">{{cite journal | vauthors = Ahlem C, Kennedy M, Page T, Bell D, Delorme E, Villegas S, Reading C, White S, Stickney D, Frincke J | title = 17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism | journal = Invest New Drugs | volume = 30 | issue = 1 | pages = 59–78 | year = 2012 | pmid = 20814732 | doi = 10.1007/s10637-010-9517-0 | url = }}</ref><ref name="pmid19337256">{{cite journal | vauthors = Trauger R, Corey E, Bell D, White S, Garsd A, Stickney D, Reading C, Frincke J | title = Inhibition of androstenediol-dependent LNCaP tumour growth by 17alpha-ethynyl-5alpha-androstane-3alpha, 17beta-diol (HE3235) | journal = Br. J. Cancer | volume = 100 | issue = 7 | pages = 1068–72 | year = 2009 | pmid = 19337256 | pmc = 2669987 | doi = 10.1038/sj.bjc.6604987 | url = }}</ref><ref name="AdisInsight">http://webcache.googleusercontent.com/search?q=cache:Jy1DYIHEUtQJ:adisinsight.springer.com/drugs/800025305</ref> It has very low [[affinity (pharmacology)|affinity]] for [[steroid receptor]]s, including the {{abbrlink|AR|androgen receptor}}, {{abbrlink|ERα|estrogen receptor alpha}}, {{abbrlink|ERβ|estrogen receptor beta}}, {{abbrlink|PR|progesterone receptor}}, and {{abbrlink|GR|glucocorticoid receptor}}, and its [[mechanism of action]] is not well-characterized.<ref name="pmid20814732" /><ref name="pmid19881957">{{cite journal | vauthors = Koreckij TD, Trauger RJ, Montgomery RB, Pitts TE, Coleman I, Nguyen H, Reading CL, Nelson PS, Vessella RL, Corey E | title = HE3235 inhibits growth of castration-resistant prostate cancer | journal = Neoplasia | volume = 11 | issue = 11 | pages = 1216–25 | year = 2009 | pmid = 19881957 | pmc = 2767223 | doi = 10.1593/neo.09960| url = }}</ref> It produces [[5α-dihydroethisterone]] as an [[active metabolite]], which may contribute importantly to its [[biological activity]].<ref name="pmid20814732" />
==Side Effects==
The use of ethynylandrostanediol, like other [[anabolic steroids]], can lead to a range of side effects. These may include:
* [[Virilization]] in women, such as deepening of the voice and increased body hair.
* [[Liver toxicity]], due to the 17α-alkylated structure.
* [[Cardiovascular issues]], such as hypertension and alterations in lipid profiles.
* [[Endocrine disruption]], including suppression of natural testosterone production.


==References==
==Legal Status==
{{Reflist}}
Ethynylandrostanediol, like many other anabolic steroids, is classified as a controlled substance in many countries. Its use is restricted to specific medical conditions and is often subject to strict regulations.


==External links==
==Related Compounds==
* [http://webcache.googleusercontent.com/search?q=cache:Jy1DYIHEUtQJ:adisinsight.springer.com/drugs/800025305 HE-3235 - AdisInsight]
Ethynylandrostanediol is related to other synthetic [[anabolic steroids]] such as [[methandrostenolone]] and [[stanozolol]]. These compounds share similar anabolic and androgenic properties but differ in their chemical structures and pharmacokinetics.


[[Category:Abandoned drugs]]
==Related Pages==
[[Category:Androstanes]]
* [[Anabolic steroid]]
[[Category:Diols]]
* [[Androgen]]
[[Category:Experimental cancer drugs]]
* [[Hormone replacement therapy]]
* [[Virilization]]
* [[Liver toxicity]]


 
[[Category:Anabolic steroids]]
{{Steroid-stub}}
[[Category:Androgens]]
{{Antineoplastic-drug-stub}}
[[Category:Synthetic hormones]]
{{dictionary-stub1}}

Latest revision as of 19:26, 22 March 2025

A synthetic anabolic-androgenic steroid


Ethynylandrostanediol is a synthetic anabolic-androgenic steroid (AAS) that was developed in the mid-20th century. It is a derivative of androstanediol, a naturally occurring androgen and anabolic steroid.

Chemical Structure[edit]

Ethynylandrostanediol is chemically known as 17α-ethynyl-5α-androstane-3β,17β-diol. It is a modified form of androstanediol, with an ethynyl group at the 17α position. This modification is intended to enhance the compound's oral bioavailability and resistance to metabolic degradation.

Pharmacology[edit]

As an anabolic-androgenic steroid, ethynylandrostanediol exhibits both androgenic and anabolic properties. It binds to androgen receptors in various tissues, promoting protein synthesis and muscle growth. The ethynyl group at the 17α position helps to prevent rapid metabolism by the liver, allowing the compound to be effective when administered orally.

Medical Uses[edit]

Ethynylandrostanediol was initially developed for potential use in hormone replacement therapy and the treatment of conditions associated with low androgen levels. However, like many other synthetic AAS, its use in clinical practice has been limited due to concerns about side effects and the availability of safer alternatives.

Side Effects[edit]

The use of ethynylandrostanediol, like other anabolic steroids, can lead to a range of side effects. These may include:

Legal Status[edit]

Ethynylandrostanediol, like many other anabolic steroids, is classified as a controlled substance in many countries. Its use is restricted to specific medical conditions and is often subject to strict regulations.

Related Compounds[edit]

Ethynylandrostanediol is related to other synthetic anabolic steroids such as methandrostenolone and stanozolol. These compounds share similar anabolic and androgenic properties but differ in their chemical structures and pharmacokinetics.

Related Pages[edit]

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