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5α-Dihydronormethandrone

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(Redirected from 5α-dihydronormethandrone) Chemical compound Pharmaceutical compound
5α-Dihydronormethandrone
Clinical data
Other names5α-DHNMT; RU-575; 17α-Methyl-4,5α-dihydro-19-nortestosterone; 17α-Methyl-5α-estran-17β-ol-3-one
Identifiers
IUPAC name
  • (5S,8R,9R,10S,13S,14S,17S)-17-Hydroxy-13,17-dimethyl-1,2,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopentaphenanthren-3-one
CAS Number
PubChem CID
UNII
Chemical and physical data
FormulaC19H30O2
Molar mass290.447 g·mol
3D model (JSmol)
SMILES
  • C12CC3(1CC2(C)O)CC43CCC(=O)C4
InChI
  • InChI=MDXRCPMWSFWIEZ-MOVWYJJTSA-N
  • Key:1S/C19H30O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15+,16+,17-,18-,19-/m0/s1

5α-Dihydronormethandrone (5α-DHNMT; developmental code name RU-575), also known as 17α-methyl-4,5α-dihydro-19-nortestosterone or as 17α-methyl-5α-estran-17β-ol-3-one, is an androgen/anabolic steroid and a likely metabolite of normethandrone formed by 5α-reductase. Analogously to nandrolone and its 5α-reduced metabolite 5α-dihydronandrolone, 5α-DHNMT shows reduced affinity for the androgen receptor relative to normethandrone. Its affinity for the androgen receptor is specifically about 33 to 60% of that of normethandrone.

Relative affinities (%) of normethandrone and metabolites
Compound PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone-binding globulin CBGTooltip Corticosteroid binding globulin
Normethandrone 75–125 125–150 <1 1–5 <1 ? ?
5α-Dihydronormethandrone 15–25 50–75 ? <1 ? ? ?
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PRTooltip progesterone receptor, testosterone for the ARTooltip androgen receptor, estradiol for the ERTooltip estrogen receptor, dexamethasone for the GRTooltip glucocorticoid receptor, and aldosterone for the MRTooltip mineralocorticoid receptor. Sources: See template.

See also

References

  1. ^ Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". J. Steroid Biochem. 27 (1–3): 255–69. doi:10.1016/0022-4731(87)90317-7. PMID 3695484.
  2. Schjølberg, T. H. (2013). In Vitro Synthesis of Metabolites of three Anabolic Androgenic Steroids, by Human Liver Microsomes (Master's thesis, Institutt for bioteknologi). https://brage.bibsys.no/xmlui/handle/11250/246018


Androgen receptor modulators
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids
Progesterone receptor modulators
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
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