Chemistry: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 | |
PubChem CID
|
|
| UNII | |
| |
| |
| 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 | |
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
- 5α-Dihydroprogesterone
- 5β-Dihydroprogesterone
- 3β-Androstanediol
- Pregnenolone
- Progesterone 3-acetyl enol ether
- Quingestrone
References
- ↑ 1.0 1.1 Kavaliers, Martin; Wiebe, John P.; Galea, Liisa A.M., 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.
- ↑ "New progesterone metabolites in human myometrium". Steroids 30 (1): 1–14. July 1977. doi:10.1016/0039-128X(77)90131-3. PMID 919010. "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.".
- ↑ "The bioassay of progesterone". Endocrinology 61 (5): 528–33. November 1957. doi:10.1210/endo-61-5-528. PMID 13480263.
 |  |
