3β-Dihydroprogesterone

Source: Wikipedia, the free encyclopedia.
3β-Dihydroprogesterone
Names
IUPAC name
3β-Hydroxypregn-4-en-20-one
Systematic IUPAC name
1-[(1S,3aS,3bS,7S,9aR,9bS,11aS)-7-Hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one
Other names
Pregn-4-en-3β-ol-20-one; 3β-Dihydroprogesterone; 3β-DHP; δ4-Pregnenolone; 4-Pregnenolone
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,15-19,23H,4-11H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
    Key: QWVWXRKHAXWWSV-QGVNFLHTSA-N
  • CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C[C@H](CC[C@]34C)O)C
Properties
C21H32O2
Molar mass 316.485 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3β-Dihydroprogesterone (3β-DHP), also known as 3β-hydroxyprogesterone, or pregn-4-en-3β-ol-20-one (4-pregnenolone, δ4-pregnenolone), is an

positive allosteric modulator of the GABAA receptor,[1] which is in accordance with the fact that other 3β-hydroxylated progesterone metabolites such as isopregnanolone and epipregnanolone similarly do not act as potentiators of this receptor and instead inhibit it as well as reverse the effects of potentiators like allopregnanolone.[2] 3β-DHP has been reported to possess about the same potency as progesterone in a bioassay of progestogenic activity, whereas 3α-DHP was not assessed.[3][4]

See also

References

  1. ^
    Wikidata Q48124086
    .
  2. S2CID 25766028
    .
  3. S2CID 28420255
    . In the Clauberg bioassay the 3β-hydroxy-4-pregnen-20-one shows about the same potency as progesterone (34). In regard to the biological activity of the 3α epimer no data are available.
  4. PMID 13480263
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=3β-Dihydroprogesterone&oldid=1151915847"