3β-Dihydroprogesterone

3β-Dihydroprogesterone (3β-DHP), also known as 3β-hydroxyprogesterone, or pregn-4-en-3β-ol-20-one (4-pregnenolone, δ4-pregnenolone), is an endogenous steroid.[1] It is biosynthesized by 3β-hydroxysteroid dehydrogenase from progesterone. Unlike 3α-dihydroprogesterone (3α-DHP), 3β-DHP does not act as a 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]

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).
Infobox references

See also

References
  1. Kavaliers, Martin; Wiebe, John P.; Galea, Liisa A.M. (1 May 1994). "Reduction of predator odor-induced anxiety in mice by the neurosteroid 3 alpha-hydroxy-4-pregnen-20-one (3 alpha HP)". Brain Research. 645 (1–2): 325–329. doi:10.1016/0006-8993(94)91667-5. ISSN 0006-8993. PMID 7914815. S2CID 53259529. Wikidata Q48124086.
  2. Prince, R.J.; Simmonds, M.A. (1993). "Differential antagonism by epipregnanolone of alphaxalone and pregnanolone potentiation of [3H]flunitrazepam binding suggests more than one class of binding site for steroids at GABAA receptors". Neuropharmacology. 32 (1): 59–63. doi:10.1016/0028-3908(93)90130-U. ISSN 0028-3908. PMID 8381526. S2CID 25766028.
  3. Junkermann H, Runnebaum B, Lisboa BP (July 1977). "New progesterone metabolites in human myometrium". Steroids. 30 (1): 1–14. doi:10.1016/0039-128X(77)90131-3. PMID 919010. 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. Pincus G, Miyake T, Merrill AP, Longo P (November 1957). "The bioassay of progesterone". Endocrinology. 61 (5): 528–33. doi:10.1210/endo-61-5-528. PMID 13480263.
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