Ethyltestosterone

Ethyltestosterone
Clinical data
Other names	17α-Ethyltestosterone; 17α-Ethylandrost-4-en-17β-ol-3-one; 17α-Pregn-4-en-17-ol-3-one
Routes of; administration	By mouth
Identifiers
	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;
CAS Number	1235-97-8 ;
PubChem CID	13908542;
ChemSpider	18504533;
UNII	4D305M9KPT;
ChEMBL	ChEMBL391236;
CompTox Dashboard (EPA)	DTXSID30924523 ;
Chemical and physical data
Formula	C21H32O2
Molar mass	316.485 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O;
	InChI InChI=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; Key: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.^[1]^[2] Like methyltestosterone, ethyltestosterone is the parent compound of many AAS.^[3] Derivatives of ethyltestosterone include norethandrolone (ethylnandrolone, ethylestrenolone), ethylestrenol (ethylnandrol), norboletone, ethyldienolone, tetrahydrogestrinone, bolenol (ethylnorandrostenol), and propetandrol.^[3]

Ethyltestosterone is described as a very weak AAS^[4]^[5] and is considerably weaker as an AAS than is methyltestosterone.^[6] It is reported to have 1/10 of the anabolic potency and 1/20 of the androgenic potency of testosterone propionate in rodents.^[7] Ethyltestosterone was also inactive in boys with dwarfism at 20 to 40 mg/day orally.^[7] The low potency of ethyltestosterone is in notable contrast to norethandrolone (17α-ethyl-19-nortestosterone), the C19 nor analogue.^[4] Analogues of ethyltestosterone with longer C17α chains such as propyltestosterone (topterone) have further reduced androgenic activity or even antiandrogenic activity.^[2]^[8] In contrast to ethyltestosterone, its 19-demethyl variant, norethandrolone, is a potent AAS comparable in anabolic activity to testosterone propionate.^[5]

References

^ Hill RA, Makin HL, Kirk DN, Murphy GM (23 May 1991). Dictionary of Steroids. CRC Press. pp. 423–. ISBN 978-0-412-27060-4.
^ ^a ^b Saunders FJ, Drill VA (May 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. PMID 13317831.
^ ^a ^b Shahidi NT (September 2001). "A review of the chemistry, biological action, and clinical applications of anabolic-androgenic steroids". Clinical Therapeutics. 23 (9): 1355–1390. doi:10.1016/s0149-2918(01)80114-4. PMID 11589254.
^ ^a ^b Camerino B, Sala G (1960). "Anabolic Steroids". Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Vol. 2. Birkhäuser. pp. 71–134. doi:10.1007/978-3-0348-7038-2_2. ISBN 978-3-0348-7040-5. PMID 14448579. {{cite book}}: ISBN / Date incompatibility (help); |journal= ignored (help)
^ ^a ^b Colton FB, Nysted LN, Riegel B, Raymond AL (1957). "17-Alkyl-19-nortestosterones". Journal of the American Chemical Society. 79 (5): 1123–1127. Bibcode:1957JAChS..79.1123C. doi:10.1021/ja01562a028. ISSN 0002-7863.
^ Rangaswami S, Seshadri TR (1952). Chemistry of vitamins and hormones. Andhra Univ.
^ ^a ^b Schedl HP, Delea C, Bartter FC (August 1959). "Structure-activity relationships of anabolic steroids: role of the 19-methyl group". The Journal of Clinical Endocrinology and Metabolism. 19 (8): 921–935. doi:10.1210/jcem-19-8-921. PMID 14442516.
^ Singh SM, Gauthier S, Labrie F (February 2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships". Current Medicinal Chemistry. 7 (2): 211–247. doi:10.2174/0929867003375371. PMID 10637363.