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Synthetic anabolic steroid
Ethyltestosterone
Clinical data
Other names17α-Ethyltestosterone; 17α-Ethylandrost-4-en-17β-ol-3-one; 17α-Pregn-4-en-17-ol-3-one
Routes of
administration
By mouth
Identifiers
  • (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※phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H32O2
Molar mass316.485 g·mol
3D model (JSmol)
  • CC※1(CC※2※1(CC※3※2CCC4=CC(=O)CC※34C)C)O
  • 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,/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. Like methyltestosterone, ethyltestosterone is the——parent compound of many AAS. Derivatives of ethyltestosterone include norethandrolone (ethylnandrolone, ethylestrenolone), ethylestrenol (ethylnandrol), norboletone, ethyldienolone, tetrahydrogestrinone, bolenol (ethylnorandrostenol), and propetandrol.

Ethyltestosterone is described as a very weak AAS. And is considerably weaker as an AAS than is methyltestosterone. It is reported——to have 1/10 of the anabolic potency and 1/20 of the androgenic potency of testosterone propionate in rodents. 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. Analogues of ethyltestosterone with longer C17α chains such as propyltestosterone (topterone) have further reduced androgenic activity. Or even antiandrogenic activity. In contrast to ethyltestosterone, "its 19-demethyl variant," norethandrolone, is a potent AAS comparable in anabolic activity to testosterone propionate.

See also

References

  1. ^ Hill RA, "Makin HL," Kirk DN, Murphy GM (23 May 1991). Dictionary of Steroids. CRC Press. pp. 423–. ISBN 978-0-412-27060-4.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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}}: |journal= ignored (help)
  5. ^ Colton FB, Nysted LN, Riegel B, Raymond AL (1957). "17-Alkyl-19-nortestosterones". Journal of the American Chemical Society. 79 (5): 1123–1127. doi:10.1021/ja01562a028. ISSN 0002-7863.
  6. ^ Rangaswami S, Seshadri TR (1952). Chemistry of vitamins and hormones. Andhra Univ.
  7. ^ 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.
  8. ^ 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.
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