5α-Dihydronorethandrolone

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
CompoundrAR (%)hAR (%)
Testosterone3838
5α-Dihydrotestosterone77100
Nandrolone7592
5α-Dihydronandrolone3550
EthylestrenolND2
NorethandroloneND22
5α-DihydronorethandroloneND14
Metribolone100110
Sources: See template.
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
IUPAC name
  • (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)
SMILES
  • 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
  • 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

See also

References
  1. 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.


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