Pregnanolone
Names | |
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IUPAC name
3α-Hydroxy-5β-pregnan-20-one
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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
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.162.192 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C21H34O2 | |
Molar mass | 318.501 g·mol−1 |
Pharmacology | |
Intravenous injection[1]
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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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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]
Biological activity
Pregnanolone is 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
Chemistry
Pregnanolone, also known as 3α,5β-tetrahydroprogesterone (3α,5β-THP) or as 5β-pregnan-3α-ol-20-one, is 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
), but produced unwantedReferences
- ^ S2CID 22005284.
- ^ S2CID 19193898.
- ^ S2CID 28358731.
- ^ PMID 15248811.
- ^ ISBN 978-3-540-74806-9.
- S2CID 9833426.
- S2CID 39391626.
[...] the fetus is sedated by the low oxygen tension of the fetal blood and the neurosteroid anesthetics pregnanolone and the sleep-inducing prostaglandin D2 provided by the placenta (36).
- ISBN 978-1-4051-9484-6.