Pregnanolone

Chemical compound From Wikipedia, the free encyclopedia

Pregnanolone, also known as eltanolone, is an endogenous inhibitory neurosteroid which is produced in the body from progesterone.[4] It is closely related to allopregnanolone, which has similar properties.[4]

Quick facts Names, Identifiers ...
Pregnanolone
Names
IUPAC name
3α-Hydroxy-5β-pregnan-20-one
Systematic IUPAC name
1-[(1S,3aS,3bR,5aR,7R,9aS,9bS,11aS)-7-Hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one
Other names
Eltanolone; 5β-Pregnan-3α-ol-20-one; 3α,5β-Tetrahydroprogesterone; 3α,5β-THP; 3α-Hydroxy-5β-tetrahydroprogesterone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.162.192 Edit this at Wikidata
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-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
Pharmacology
Intravenous injection[1]
Pharmacokinetics:
0.9–3.5 hours[1][2][3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biological activity

Pregnanolone is a positive allosteric modulator of the GABAA receptor,[4] as well as a negative allosteric modulator of the glycine receptor.[5]

Biological function

Pregnanolone has sedative, anxiolytic, anesthetic, and anticonvulsant effects.[4][5][1] During pregnancy, pregnanolone and allopregnanolone are involved in sedation and anesthesia of the fetus.[6][7]

Biochemistry

Pregnanolone is synthesized from progesterone via the enzymes 5β-reductase and 3α-hydroxysteroid dehydrogenase, with 5β-dihydroprogesterone occurring as a metabolic intermediate. The elimination half-life of pregnanolone is between 0.9 and 3.5 hours.[1][2][3]

Chemistry

See also: List of neurosteroids

Pregnanolone, also known as 3α,5β-tetrahydroprogesterone (3α,5β-THP) or as 5β-pregnan-3α-ol-20-one, is a naturally occurring pregnane steroid and a derivative of progesterone. Related compounds include allopregnanolone (3α,5α-THP; brexanolone), epipregnanolone (3β,5β-THP), hydroxydione, isopregnanolone (3β,5α-THP), and renanolone.

History

Pregnanolone was first isolated from the urine of pregnant women in 1937.[1] Its anesthetic properties were first demonstrated in animals in 1957.[1]

Research

Pregnanolone was investigated for clinical use as a general anesthetic under the name eltanolone (INNTooltip International Nonproprietary Name), but produced unwanted side effects such as convulsions on occasion, and for this reason, was never marketed.[5][8][1]

References

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