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5α-Dihydronorethandrolone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
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 as17α-ethyl-4,5α-dihydro-19-nortestosterone or as17α-ethyl-5α-estran-17β-ol-3-one, is anandrogen/anabolic steroid and ametabolite ofnorethandrolone (as well as of theprodrugethylestrenol) formed by5α-reductase.[1] Analogously tonandrolone and its 5α-reduced metabolite5α-dihydronandrolone, 5α-DHNED shows reducedaffinity for theandrogen 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.

See also

[edit]

References

[edit]
  1. ^abcBergink 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.


ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
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