3α-Hydroxytibolone

3α-Hydroxytibolone (developmental code name ORG-4094) is a synthetic steroidal estrogen which was never marketed.[1][2] Along with 3β-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]

3α-Hydroxytibolone
Clinical data
Other namesORG-4094; 7α-Methyl-17α-ethynylestr-5(10)-ene-3α,17β-diol
Identifiers
  • (3R,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
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-CZTKNSHGSA-N

References
  1. 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. S2CID 24616324.
  2. 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. S2CID 18346113.



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