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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
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
C21 H32 O2
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).
Chemical compound
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]
See also
References
^
a
b 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 .
^ 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 .
^ 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.
^ 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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RU-2309
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