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Epipregnanolone

December 15, 2023

Epipregnanolone, also known as 3β-hydroxy-5β-pregnan-20-one, 3β,5β-tetrahydroprogesterone, or 3β,5β-THP, is an endogenous neurosteroid.[1] It acts as a negative allosteric modulator of the GABAA receptor and reverses the effects of potentiators like allopregnanolone.[2][3] Epipregnanolone is biosynthesized from progesterone by the actions of 5β-reductase and 3β-hydroxysteroid dehydrogenase, with 5β-dihydroprogesterone as the intermediate in this two-step transformation.[2]

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
  • 128-21-2 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 198867
  • 228491
UNII
  • 3KQ00893OL Y
  • DTXSID00155766
  • 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 mass 318.501 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

The sulfate of epipreganolone, epipregnanolone sulfate, is a negative allosteric modulator of the NMDA[5] and GABAA receptors[6] and also acts as a TRPM3 channel activator.[7][8]

Chemistry edit

See also: List of neurosteroids

See also edit

References edit

  1. ^ Neurosteroids and Brain Function. Academic Press. 12 December 2001. pp. 18–. ISBN 978-0-08-054423-6.
  2. ^ a b Abraham 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.

December 15, 2023
epipregnanolone, also, known, hydroxy, pregnan, tetrahydroprogesterone, endogenous, neurosteroid, acts, negative, allosteric, modulator, gabaa, receptor, reverses, effects, potentiators, like, allopregnanolone, biosynthesized, from, progesterone, actions, redu. Epipregnanolone also known as 3b hydroxy 5b pregnan 20 one 3b 5b tetrahydroprogesterone or 3b 5b THP is an endogenous neurosteroid 1 It acts as a negative allosteric modulator of the GABAA receptor and reverses the effects of potentiators like allopregnanolone 2 3 Epipregnanolone is biosynthesized from progesterone by the actions of 5b reductase and 3b hydroxysteroid dehydrogenase with 5b dihydroprogesterone as the intermediate in this two step transformation 2 Epipregnanolone NamesIUPAC name 3b Hydoxy 5b pregnan 20 oneSystematic IUPAC name 1 1S 3aS 3bR 5aR 7S 9aS 9bS 11aS 7 Hydroxy 9a 11a dimethylhexadecahydro 1H cyclopenta a phenanthren 1 yl ethan 1 oneOther names 3b 5b TetrahydroprogesteroneIdentifiersCAS Number 128 21 2 Y3D model JSmol Interactive imageChemSpider 198867PubChem CID 228491UNII 3KQ00893OL YCompTox Dashboard EPA DTXSID00155766InChI 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 s1Key AURFZBICLPNKBZ GRWISUQFSA NSMILES 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 CPropertiesChemical formula C 21H 34O 2Molar mass 318 501 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Epipregnanolone is not a progestogen itself but via metabolization into other steroids behaves indirectly as one 4 The sulfate of epipreganolone epipregnanolone sulfate is a negative allosteric modulator of the NMDA 5 and GABAA receptors 6 and also acts as a TRPM3 channel activator 7 8 Chemistry editSee also List of neurosteroidsSee also editIsopregnanolone 3b Dihydroprogesterone Pregnanolone 5a Dihydroprogesterone 3b AndrostanediolReferences edit Neurosteroids and Brain Function Academic Press 12 December 2001 pp 18 ISBN 978 0 08 054423 6 a b Abraham Weizman 1 February 2008 Neuroactive Steroids in Brain Function Behavior and Neuropsychiatric Disorders Novel Strategies for Research and Treatment Springer Science amp Business Media pp 6 ISBN 978 1 4020 6854 6 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 Beyer C Gonzalez Flores O Rami rez Orduna J M Gonzalez Mariscal G 1999 Indomethacin Inhibits Lordosis Induced by Ring A Reduced Progestins Possible Role of 3a 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 Norman G Bowery 19 June 2006 Allosteric Receptor Modulation in Drug Targeting CRC Press pp 112 ISBN 978 1 4200 1618 5 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 Issues in Pharmacology Pharmacy Drug Research and Drug Innovation 2011 Edition ScholarlyEditions 9 January 2012 pp 3260 ISBN 978 1 4649 6342 1 Advances in Glutamic Acid Research and Application 2013 Edition ScholarlyBrief ScholarlyEditions 21 June 2013 pp 104 ISBN 978 1 4816 7049 4 Retrieved from https en wikipedia org w index php title Epipregnanolone amp oldid 1184914575, wikipedia, wiki, book, books, library,

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