Ethyltestosterone

{{Short description|Synthetic anabolic steroid}}

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| IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-ethyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one

| image = Ethyltestosterone_structure.png

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| routes_of_administration = By mouth

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| CAS_number = 1235-97-8

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| UNII = 4D305M9KPT

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| PubChem = 13908542

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| ChemSpiderID = 18504533

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| ChEMBL = 391236

| synonyms = 17α-Ethyltestosterone; 17α-Ethylandrost-4-en-17β-ol-3-one; 17α-Pregn-4-en-17-ol-3-one

| 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

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| StdInChIKey = FGPGANCDNDLUST-CEGNMAFCSA-N

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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.{{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–}}{{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 }} Like methyltestosterone, ethyltestosterone is the parent compound of many AAS.{{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 }} Derivatives of ethyltestosterone include norethandrolone (ethylnandrolone, ethylestrenolone), ethylestrenol (ethylnandrol), norboletone, ethyldienolone, tetrahydrogestrinone, bolenol (ethylnorandrostenol), and propetandrol.

Ethyltestosterone is described as a very weak AAS{{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 }} and is considerably weaker as an AAS than is methyltestosterone.{{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.}} It is reported to have 1/10 of the anabolic potency and 1/20 of the androgenic potency of testosterone propionate in rodents.{{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 }} Ethyltestosterone was also inactive in boys with dwarfism at 20 to 40 mg/day orally. The low potency of ethyltestosterone is in notable contrast to norethandrolone (17α-ethyl-19-nortestosterone), the C19 nor analogue.{{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}} Analogues of ethyltestosterone with longer C17α chains such as propyltestosterone (topterone) have further reduced androgenic activity or even antiandrogenic activity.{{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 }} In contrast to ethyltestosterone, its 19-demethyl variant, norethandrolone, is a potent AAS comparable in anabolic activity to testosterone propionate.