3β-Hydroxytibolone

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3β-Hydroxytibolone
Clinical data
Other namesORG-30126; 7α-Methyl-17α-ethynylestr-5(10)-ene-3β,17β-diol
Identifiers
  • (3S,7R,8R,9S,13S,14S,17R)-17-ethynyl-7,13-dimethyl-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
  • C[C@@H]1CC2=C(CC[C@@H](C2)O)[C@@H]3[C@@H]1[C@@H]4CC[C@]([C@]4(CC3)C)(C#C)O
  • InChI=1S/C21H30O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,13,15,17-19,22-23H,5-12H2,2-3H3/t13-,15+,17-,18+,19-,20+,21+/m1/s1
  • Key:YLEUWNOTNJZCBN-XAAPQAIWSA-N

3β-Hydroxytibolone (developmental code name ORG-30126) is a synthetic steroidal estrogen which was never marketed.[1][2] Along with 3α-hydroxytibolone and δ4-tibolone, it is a major active metabolite of tibolone, and 3α-hydroxytibolone and 3β-hydroxytibolone are thought to be responsible for the estrogenic activity of tibolone.[1][2]

Relative affinities (%) of noretynodrel, tibolone, and metabolites
Compound Code name PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone-binding globulin CBGTooltip Corticosteroid binding globulin
Noretynodrel – 6 0 2 0 0 0 0
  Norethisterone (δ4-NYD) – 67–75 15 0 0–1 0–3 16 0
  3α-Hydroxynoretynodrel – ? ? ? ? ? ? ?
  3β-Hydroxynoretynodrel – ? ? ? ? ? ? ?
  Ethinylestradiol – 15–25 1–3 112 1–3 <1 0.18 <0.1
Tibolone (7α-Me-NYD) ORG-OD-14 6 6 1 ? ? ? ?
  Δ4-Tibolone ORG-OM-38 90 35 1 0 2 1 0
  3α-Hydroxytibolone ORG-4094 0 3 4–6 0 ? ? ?
  3β-Hydroxytibolone ORG-301260 0 4 3–29 0 ? ? ?
  7α-Methylethinylestradiol – ? ? ? ? ? ? ?
Notes: Values are percentages (%). Reference ligands (100%) were promegestone for the PRTooltip progesterone receptor, metribolone for the ARTooltip androgen receptor, E2 for the ERTooltip estrogen receptor, DEXATooltip dexamethasone for the GRTooltip glucocorticoid receptor, aldosterone for the MRTooltip mineralocorticoid receptor, DHTTooltip dihydrotestosterone for SHBGTooltip sex hormone-binding globulin, and cortisol for CBGTooltip Corticosteroid-binding globulin. Sources: See template.

Template:Absolute activities of tibolone and metabolites

References

  1. ^ a b Kuhl, H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (sup1): 3–63. doi:10.1080/13697130500148875. ISSN 1369-7137. PMID 16112947.
  2. ^ a b Escande A, Servant N, Rabenoelina F, Auzou G, Kloosterboer H, Cavaillès V, Balaguer P, Maudelonde T (2009). "Regulation of activities of steroid hormone receptors by tibolone and its primary metabolites". J. Steroid Biochem. Mol. Biol. 116 (1–2): 8–14. doi:10.1016/j.jsbmb.2009.03.008. PMID 19464167.



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