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5α-Dihydronorethandrolone

From Wikipedia, the free encyclopedia

5α-Dihydronorethandrolone
Clinical data
Other names5α-DHNED; 4,5α-Dihydronorethandrolone; 3-Keto-5α-dihydroethylestrenol; 17α-Ethyl-5α-dihydro-19-nortestosterone; 17α-Ethyl-5α-estran-17β-ol-3-one; 19-Nor-5α-pregnan-17α-ol-3-one
Identifiers
  • (5S,8R,9R,10S,13S,14S,17S)-17-Ethyl-17-hydroxy-13-methyl-1,2,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H32O2
Molar mass304.474 g·mol−1
3D model (JSmol)
  • CC[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@H]3CCC(=O)C4)C)O
  • InChI=1S/C20H32O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h13,15-18,22H,3-12H2,1-2H3/t13-,15-,16+,17+,18-,19-,20-/m0/s1
  • Key:IOLODVBMNDJVOP-XDQPPUBWSA-N

5α-Dihydronorethandrolone (5α-DHNED), also known as 17α-ethyl-4,5α-dihydro-19-nortestosterone or as 17α-ethyl-5α-estran-17β-ol-3-one, is an androgen/anabolic steroid and a metabolite of norethandrolone (as well as of the prodrug ethylestrenol) formed by 5α-reductase.[1] Analogously to nandrolone and its 5α-reduced metabolite 5α-dihydronandrolone, 5α-DHNED shows reduced affinity for the androgen receptor relative to norethandrolone.[1] Its affinity for the androgen receptor is specifically about 64% of that of norethandrolone.[1]

Relative affinities of nandrolone and related steroids at the androgen receptor
Compound rAR (%) hAR (%)
Testosterone 38 38
5α-Dihydrotestosterone 77 100
Nandrolone 75 92
5α-Dihydronandrolone 35 50
Ethylestrenol ND 2
Norethandrolone ND 22
5α-Dihydronorethandrolone ND 14
Metribolone 100 110
Sources: See template.

See also

References

  1. ^ a b c Bergink EW, Geelen JA, Turpijn EW (1985). "Metabolism and receptor binding of nandrolone and testosterone under in vitro and in vivo conditions". Acta Endocrinol Suppl (Copenh). 271 (3_Suppla): 31–7. doi:10.1530/acta.0.109S0031. PMID 3865479.


This page was last edited on 11 November 2023, at 17:43
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