{{Short description|Synthetic anabolic steroid}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-17-ethyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1''H''-cyclopenta[''a'']phenanthren-3-one | image = Ethyltestosterone_structure.png | image_class = skin-invert-image | width = 250px
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 1235-97-8 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 4D305M9KPT | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 13908542 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 18504533 | KEGG = | ChEBI = | ChEMBL = 391236 | synonyms = 17α-Ethyltestosterone; 17α-Ethylandrost-4-en-17β-ol-3-one; 17α-Pregn-4-en-17-ol-3-one
<!--Chemical data--> | C=21 | H=32 | O=2 | SMILES = CC[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)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/h13,16-18,23H,4-12H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = FGPGANCDNDLUST-CEGNMAFCSA-N }}
'''Ethyltestosterone''', or '''17α-ethyltestosterone''', also known as '''17α-ethylandrost-4-en-17β-ol-3-one''' or '''17α-pregn-4-en-17-ol-3-one''', is a synthetic, orally active anabolic–androgenic steroid (AAS) of the 17α-alkylated group related to methyltestosterone which was never marketed.<ref name="HillMakin1991">{{cite book | vauthors = Hill RA, Makin HL, Kirk DN, Murphy GM |title=Dictionary of Steroids |url=https://books.google.com/books?id=AI7EnUyeEtUC&pg=PA423 |date=23 May 1991 |publisher=CRC Press |isbn=978-0-412-27060-4 |pages=423–}}</ref><ref name="SaundersDrill1956">{{cite journal | vauthors = Saunders FJ, Drill VA | title = The myotrophic and androgenic effects of 17-ethyl-19-nortestosterone and related compounds | journal = Endocrinology | volume = 58 | issue = 5 | pages = 567–572 | date = May 1956 | pmid = 13317831 | doi = 10.1210/endo-58-5-567 }}</ref> Like methyltestosterone, ethyltestosterone is the parent compound of many AAS.<ref name="pmid11589254">{{cite journal | vauthors = Shahidi NT | title = A review of the chemistry, biological action, and clinical applications of anabolic-androgenic steroids | journal = Clinical Therapeutics | volume = 23 | issue = 9 | pages = 1355–1390 | date = September 2001 | pmid = 11589254 | doi = 10.1016/s0149-2918(01)80114-4 }}</ref> Derivatives of ethyltestosterone include norethandrolone (ethylnandrolone, ethylestrenolone), ethylestrenol (ethylnandrol), norboletone, ethyldienolone, tetrahydrogestrinone, bolenol (ethylnorandrostenol), and propetandrol.<ref name="pmid11589254" />
Ethyltestosterone is described as a very weak AAS<ref name="CamerinoSala1960" /><ref name="ColtonNysted1957">{{cite journal| vauthors = Colton FB, Nysted LN, Riegel B, Raymond AL |title=17-Alkyl-19-nortestosterones|journal=Journal of the American Chemical Society|volume=79|issue=5|year=1957|pages=1123–1127|issn=0002-7863|doi=10.1021/ja01562a028|bibcode=1957JAChS..79.1123C }}</ref> and is considerably weaker as an AAS than is methyltestosterone.<ref name="RangaswamiSeshadri1952">{{cite book| vauthors = Rangaswami S, Seshadri TR |title=Chemistry of vitamins and hormones|url=https://books.google.com/books?id=woQZAAAAIAAJ|year=1952|publisher=Andhra Univ.}}</ref> It is reported to have 1/10 of the anabolic potency and 1/20 of the androgenic potency of testosterone propionate in rodents.<ref name="pmid14442516">{{cite journal | vauthors = Schedl HP, Delea C, Bartter FC | title = Structure-activity relationships of anabolic steroids: role of the 19-methyl group | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 19 | issue = 8 | pages = 921–935 | date = August 1959 | pmid = 14442516 | doi = 10.1210/jcem-19-8-921 }}</ref> Ethyltestosterone was also inactive in boys with dwarfism at 20 to 40 mg/day orally.<ref name="pmid14442516" /> The low potency of ethyltestosterone is in notable contrast to norethandrolone (17α-ethyl-19-nortestosterone), the C19 nor analogue.<ref name="CamerinoSala1960">{{cite book| vauthors = Camerino B, Sala G |journal=Fortschritte der Arzneimittelforschung. Progress in Drug Research. Progres des Recherches Pharmaceutiques |title=Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques |chapter=Anabolic Steroids|year=1960|volume=2|pages=71–134|publisher=Birkhäuser |doi=10.1007/978-3-0348-7038-2_2|pmid=14448579|isbn=978-3-0348-7040-5}}</ref> Analogues of ethyltestosterone with longer C17α chains such as propyltestosterone (topterone) have further reduced androgenic activity or even antiandrogenic activity.<ref name="SaundersDrill1956" /><ref name="pmid10637363">{{cite journal | vauthors = Singh SM, Gauthier S, Labrie F | title = Androgen receptor antagonists (antiandrogens): structure-activity relationships | journal = Current Medicinal Chemistry | volume = 7 | issue = 2 | pages = 211–247 | date = February 2000 | pmid = 10637363 | doi = 10.2174/0929867003375371 }}</ref> In contrast to ethyltestosterone, its 19-demethyl variant, norethandrolone, is a potent AAS comparable in anabolic activity to testosterone propionate.<ref name="ColtonNysted1957" />
== See also == * List of androgens/anabolic steroids
== References == {{Reflist|30em}}
{{Androgen receptor modulators}}
Category:Abandoned drugs Category:1-Ethylcyclopentanols Category:Androgens Category:Androstanes Category:Enones
{{Androgen-stub}} {{Genito-urinary-drug-stub}} {{Gastrointestinal-drug-stub}}