Pregnanolone

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Pregnanolone
Names
IUPAC name
(3α,5β)-3-Hydroxypregnan-20-one
Other names
Eltanolone; 5β-Pregnan-3α-ol-20-one; 3α-Hydroxy-5β-pregnan-20-one; 3α-Hydroxy-5β-tetrahydroprogesterone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.162.192 Edit this at Wikidata
  • 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-YZRLXODZSA-N
  • InChI=1/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-YZRLXODZBF
  • 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).
This article is about the 3α,5β-reduced metabolite of progesterone. For other pregnanolone isomers of progesterone, see Pregnanolone (disambiguation).

Pregnanolone, also known as eltanolone (INN), as well as 3α,5β-tetrahydroprogesterone (3α,5β-THP) or 3α-hydroxy-5β-pregnan-20-one, is an endogenous neurosteroid that is biosynthesized from progesterone.[1] It is a positive allosteric modulator of the GABAA receptor,[1] as well as a negative allosteric modulator of the glycine receptor,[2] and is known to have sedative, anxiolytic, anesthetic, and anticonvulsant effects.[1][2][3] It was investigated for clinical use as a general anesthetic, but produced unwanted side effects such as convulsions on occasion, and for that reason was never marketed.[2][4]

See also

References

  1. ^ a b c Reddy DS (2003). "Pharmacology of endogenous neuroactive steroids". Crit Rev Neurobiol. 15 (3–4): 197–234. doi:10.1615/critrevneurobiol.v15.i34.20. PMID 15248811.
  2. ^ a b c Jürgen Schüttler; Helmut Schwilden (8 January 2008). Modern Anesthetics. Springer Science & Business Media. pp. 278–. ISBN 978-3-540-74806-9.
  3. ^ Carl P, Høgskilde S, Lang-Jensen T, et al. (October 1994). "Pharmacokinetics and pharmacodynamics of eltanolone (pregnanolone), a new steroid intravenous anaesthetic, in humans". Acta Anaesthesiol Scand. 38 (7): 734–41. doi:10.1111/j.1399-6576.1994.tb03987.x. PMID 7839787.
  4. ^ Norman Calvey; Norton Williams (21 January 2009). Principles and Practice of Pharmacology for Anaesthetists. John Wiley & Sons. pp. 110–. ISBN 978-1-4051-9484-6.


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