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Epipregnanolone

From Wikipedia, the free encyclopedia
Epipregnanolone
Names
IUPAC name
3β-Hydoxy-5β-pregnan-20-one
Systematic IUPAC name
1-[(1S,3aS,3bR,5aR,7S,9aS,9bS,11aS)-7-Hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one
Other names
3β,5β-Tetrahydroprogesterone
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C21H34O2/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/h14-19,23H,4-12H2,1-3H3/t14-,15+,16+,17-,18+,19+,20+,21-/m1/s1
    Key: AURFZBICLPNKBZ-GRWISUQFSA-N
  • CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@@H](C4)O)C)C
Properties
C21H34O2
Molar mass318.501 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Epipregnanolone, also known as3β-hydroxy-5β-pregnan-20-one,3β,5β-tetrahydroprogesterone, or3β,5β-THP, is anendogenousneurosteroid.[1] It acts as anegative allosteric modulator of theGABAA receptor and reverses the effects ofpotentiators likeallopregnanolone.[2][3] Epipregnanolone isbiosynthesized fromprogesterone by the actions of5β-reductase and3β-hydroxysteroid dehydrogenase, with5β-dihydroprogesterone as theintermediate in this two-step transformation.[2]

Epipregnanolone is not aprogestogen itself, but via metabolization into other steroids, behaves indirectly as one.[4]

Thesulfate of epipreganolone,epipregnanolone sulfate, is a negative allosteric modulator of theNMDA[5] andGABAA receptors[6] and also acts as aTRPM3channel activator.[7][8]

Chemistry

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See also:List of neurosteroids

See also

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References

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  1. ^Neurosteroids and Brain Function. Academic Press. 12 December 2001. pp. 18–.ISBN 978-0-08-054423-6.
  2. ^abAbraham Weizman (1 February 2008).Neuroactive Steroids in Brain Function, Behavior and Neuropsychiatric Disorders: Novel Strategies for Research and Treatment. Springer Science & Business Media. pp. 6–.ISBN 978-1-4020-6854-6.
  3. ^Jan Egebjerg; Arne Schousboe; Povl Krogsgaard-Larsen (4 October 2001).Glutamate and GABA Receptors and Transporters: Structure, Function and Pharmacology. CRC Press. pp. 248–.ISBN 978-0-7484-0881-8.
  4. ^Beyer, C.; González-Flores, O.; Ramı́rez-Orduña, J.M.; González-Mariscal, G. (1999). "Indomethacin Inhibits Lordosis Induced by Ring A-Reduced Progestins: Possible Role of 3α-Oxoreduction in Progestin-Facilitated Lordosis".Hormones and Behavior.35 (1):1–8.doi:10.1006/hbeh.1998.1457.ISSN 0018-506X.PMID 10049597.S2CID 11520064.
  5. ^Norman G. Bowery (19 June 2006).Allosteric Receptor Modulation in Drug Targeting. CRC Press. pp. 112–.ISBN 978-1-4200-1618-5.
  6. ^Park-Chung M, Malayev A, Purdy RH, Gibbs TT, Farb DH (1999)."Sulfated and unsulfated steroids modulate gamma-aminobutyric acidA receptor function through distinct sites".Brain Res.830 (1):72–87.doi:10.1016/s0006-8993(99)01381-5.PMID 10350561.S2CID 44664830.
  7. ^Issues in Pharmacology, Pharmacy, Drug Research, and Drug Innovation: 2011 Edition. ScholarlyEditions. 9 January 2012. pp. 3260–.ISBN 978-1-4649-6342-1.
  8. ^Advances in Glutamic Acid Research and Application: 2013 Edition: ScholarlyBrief. ScholarlyEditions. 21 June 2013. pp. 104–.ISBN 978-1-4816-7049-4.
Precursors
Corticosteroids
Glucocorticoids
Mineralocorticoids
Sex steroids
Androgens
Estrogens
Progestogens
Neurosteroids
Others
Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAA-ρTooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
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