17α-Alkylated anabolic steroid

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A 17α-alkylated anabolic steroid is a synthetic anabolic–androgenic steroid (AAS) that features an alkyl group, specifically a methyl or ethyl group, at the C17α position. Unlike many other AAS, 17α-alkylated AAS are orally active and do not require intramuscular injection. However, they uniquely possess a high potential for hepatotoxicity, which simultaneously limits their use. In addition, some have a high risk of gynecomastia due to uniquely high estrogenic activity, although this does not apply to 17α-alkylated AAS that are also 4,5α-reduced or 19-demethylated (i.e., that are also dihydrotestosterone (DHT) or nandrolone derivatives, respectively). The prototypical example of a 17α-alkylated AAS is methyltestosterone (17α-methyltestosterone).

Structure-activity relationships

Extension of the C17α alkyl chain longer than an ethyl group abolishes androgenic activity and converts the drug into an antiandrogen, as in topterone (17α-propyltestosterone) and allylestrenol (17α-allyl-3-deketo-19-nortestosterone) (an extended-chain variant of ethylestrenol). Conversely, replacement of the C17α alkyl group with an ethynyl group greatly reduces but does not abolish androgenic activity, as in ethisterone (17α-ethynyltestosterone) and norethisterone (17α-ethynyl-19-nortestosterone).[1] Similarly to extension of the C17α alkyl chain, extension of the C17α ethynyl chain abolishes androgenic activity, as with dimethisterone (6α,21-dimethylethisterone). Dienogest, which is antiandrogenic, features extension of the C17α chain in the form of a cyanomethyl group at the C17α position.

List of 17α-alkylated AAS

See also

References

  1. ↑ Saunders, Francis J.; Drill, Victor A. (1956). "The Myotrophic and Androgenic Effects of 17-Ethyl-19-Nortestosterone and Related Compounds". Endocrinology. 58 (5): 567–572. doi:10.1210/endo-58-5-567. ISSN 0013-7227. PMID 13317831.
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