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;
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 1/10th of the anabolic potency and 1/20th 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

^ R.A. Hill; H.L.J. Makin; D.N. Kirk; G.M. Murphy (23 May 1991). Dictionary of Steroids. CRC Press. pp. 423–. ISBN 978-0-412-27060-4.
^ ^a ^b 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.
^ ^a ^b Shahidi NT (2001). "A review of the chemistry, biological action, and clinical applications of anabolic-androgenic steroids". Clin Ther. 23 (9): 1355–90. 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. pp. 71–134. doi:10.1007/978-3-0348-7038-2_2. ISBN 978-3-0348-7040-5.
^ ^a ^b Colton, Frank B.; Nysted, Leonard N.; Riegel, Byron; Raymond, Albert L (1957). "17-Alkyl-19-nortestosterones". Journal of the American Chemical Society. 79 (5): 1123–1127. doi:10.1021/ja01562a028. ISSN 0002-7863.
^ Srinivasa Rangaswami; Tiruvenkata Rajendra Seshadri (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". J. Clin. Endocrinol. Metab. 19: 921–35. doi:10.1210/jcem-19-8-921. PMID 14442516.
^ Singh SM, Gauthier S, Labrie F (2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships". Curr. Med. Chem. 7 (2): 211–47. doi:10.2174/0929867003375371. PMID 10637363.

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[HillMakin1991-1] R.A. Hill; H.L.J. Makin; D.N. Kirk; G.M. Murphy (23 May 1991). Dictionary of Steroids. CRC Press. pp. 423–. ISBN 978-0-412-27060-4.

[SaundersDrill1956-2] 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.

[pmid11589254-3] Shahidi NT (2001). "A review of the chemistry, biological action, and clinical applications of anabolic-androgenic steroids". Clin Ther. 23 (9): 1355–90. doi:10.1016/s0149-2918(01)80114-4. PMID 11589254.

[CamerinoSala1960-4] Camerino, B.; Sala, G. (1960). "Anabolic Steroids". Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. pp. 71–134. doi:10.1007/978-3-0348-7038-2_2. ISBN 978-3-0348-7040-5.

[ColtonNysted1957-5] Colton, Frank B.; Nysted, Leonard N.; Riegel, Byron; Raymond, Albert L (1957). "17-Alkyl-19-nortestosterones". Journal of the American Chemical Society. 79 (5): 1123–1127. doi:10.1021/ja01562a028. ISSN 0002-7863.

[RangaswamiSeshadri1952-6] Srinivasa Rangaswami; Tiruvenkata Rajendra Seshadri (1952). Chemistry of vitamins and hormones. Andhra Univ.

[pmid14442516-7] SCHEDL HP, DELEA C, BARTTER FC (August 1959). "Structure-activity relationships of anabolic steroids: role of the 19-methyl group". J. Clin. Endocrinol. Metab. 19: 921–35. doi:10.1210/jcem-19-8-921. PMID 14442516.

[pmid10637363-8] Singh SM, Gauthier S, Labrie F (2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships". Curr. Med. Chem. 7 (2): 211–47. doi:10.2174/0929867003375371. PMID 10637363.

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See also

References