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δ4-Tibolone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Δ4-Tibolone
Clinical data
Other namesORG-OM-38; Delta-4-Tibolone; 7α-Methylnorethisterone; 7α-Methyl-17α-ethynyl-19-nortestosterone; 17α-Ethynyl-17β-hydroxy-7α-methyl-4-estren-3-one
Identifiers
  • (7R,8R,9S,10R,13S,14S,17R)-17-Ethynyl-17-hydroxy-7,13-dimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChemCID
ChemSpider
UNII
Chemical and physical data
FormulaC21H28O2
Molar mass312.453 g·mol−1
3D model (JSmol)
  • C[C@@H]1CC2=CC(=O)CC[C@@H]2[C@@H]3[C@@H]1[C@@H]4CC[C@]([C@]4(CC3)C)(C#C)O
  • InChI=1S/C21H28O2/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/h1,12-13,16-19,23H,5-11H2,2-3H3/t13-,16+,17-,18+,19-,20+,21+/m1/s1
  • Key:WAOKMNBZWBGYIK-KIURNNQRSA-N

δ4-Tibolone (developmental code nameORG-OM-38), also known as7α-methylnorethisterone or as7α-methyl-17α-ethynyl-19-nortestosterone, is asyntheticandrogen andprogestin which was never marketed.[1][2] The compound is a majoractive metabolite oftibolone, which itself is aprodrug of δ4-tibolone along with3α-hydroxytibolone and3β-hydroxytibolone (which, in contrast to δ4-tibolone, areestrogens).[1] Tibolone and δ4-tibolone are thought to be responsible for the androgenic and progestogenic activity of tibolone, while 3α-hydroxytibolone and 3β-hydroxytibolone are thought to be responsible for itsestrogenic activity.[1]

See also

[edit]

References

[edit]
  1. ^abcKuhl H (2005)."Pharmacology of estrogens and progestogens: influence of different routes of administration"(PDF).Climacteric.8 (Suppl 1):3–63.doi:10.1080/13697130500148875.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.


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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