Epipregnanolone

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
CAS Number	128-21-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	198867;
PubChem CID	228491;
UNII	3KQ00893OL ;
CompTox Dashboard (EPA)	DTXSID00155766 ;
	InChI 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;
	SMILES 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
Chemical formula	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). Infobox references

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 GABA_A 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 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 GABA_A receptors^[6] and also acts as a TRPM3 channel activator.^[7]^[8]

Chemistry

References

^ 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 & 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.; 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.
^ 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.

[1] Neurosteroids and Brain Function. Academic Press. 12 December 2001. pp. 18–. ISBN 978-0-08-054423-6.

[Weizman2008-2] 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.

[EgebjergSchousboe2001-3] 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.

[BeyerGonzález-Flores1999-4] 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.

[Bowery2006-5] Norman G. Bowery (19 June 2006). Allosteric Receptor Modulation in Drug Targeting. CRC Press. pp. 112–. ISBN 978-1-4200-1618-5.

[pmid10350561-6] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

Epipregnanolone

Chemistry

See also

References