5β-Dihydroprogesterone

Source: Wikipedia, the free encyclopedia.
5β-Dihydroprogesterone
Names
IUPAC name
5β-Pregnane-3,20-dione
Systematic IUPAC name
(1S,3aS,3bR,5aR,9aS,9bS,11aS)-1-Acetyl-9a,11a-dimethylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one
Other names
Pregnanedione
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CCC(=O)C4)C)C
Properties
C21H32O2
Molar mass 316.485 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

5β-Dihydroprogesterone (5β-DHP, pregnanedione, or 5β-pregnane-3,20-dione) is an

5β-reductase.[1][4]

5β-DHP has been found to act as a

rhesus monkey uterus), and in relation to this, is not a notable progestogen.[13][14]

A study found that 5β-DHP, but not progesterone, directly bound to and

nanomolar concentrations, and it was suggested that this may be one of the mechanisms by which progesterone maintains pregnancy.[15][16][17] However, a subsequent study was unable to replicate this finding, and there has been no further investigation since.[16] In any case, 5β-DHP has nonetheless been shown to possess tocolytic effects in animals, and this may alternatively be mediated by activation of the PXR.[12]

See also

References

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  12. ^
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  13. S2CID 40245594
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  14. PMID 405534
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  16. ^
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  17. ISBN 978-0-08-053527-2
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