P8129
5β-Pregnan-3α-ol-20-one
Sinónimos:
3α-Hydroxy-5β-pregnan-20-one, 3α-Hydroxy-5β-tetrahydroprogesterone, Pregnanolone
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About This Item
Fórmula empírica (notación de Hill):
C21H34O2
Número de CAS:
Peso molecular:
318.49
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
biological source:
synthetic (organic)
form:
powder
assay:
≥98% (TLC)
Productos recomendados
biological source
synthetic (organic)
Quality Level
assay
≥98% (TLC)
form
powder
solubility
chloroform: 50 mg/mL, clear, colorless
shipped in
ambient
storage temp.
room temp
SMILES string
[H]C12CCC3C4CCC(C(C)=O)C4(C)CCC3C1(C)CC[C@H](O)C2
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
InChI key
AURFZBICLPNKBZ-UHFFFAOYSA-N
Gene Information
rat ... Gabra2(29706)
Biochem/physiol Actions
5β-Pregnan-3α-ol-20-one or pregnanolone is a neurosteroid that acts as a positive allosteric modulator (PAMs) of γ-aminobutyric acid A receptors (GABAARs). It mediates anti-convulsive, anxiolytic and sedative effects. Pregnanolone inhibits γ-aminobutyric acid C receptor (GABAC) receptor-based response and favors GABAA receptor-mediated currents.
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Selwyn S Jayakar et al.
The Journal of biological chemistry, 295(33), 11495-11512 (2020-06-17)
Allopregnanolone (3α5α-P), pregnanolone, and their synthetic derivatives are potent positive allosteric modulators (PAMs) of GABAA receptors (GABAARs) with in vivo anesthetic, anxiolytic, and anti-convulsant effects. Mutational analysis, photoaffinity labeling, and structural studies have provided evidence for intersubunit and intrasubunit steroid-binding
P Li et al.
British journal of pharmacology, 171(23), 5446-5457 (2014-08-15)
Neurosteroids potentiate responses of the GABAA receptor to the endogenous agonist GABA. Here, we examined the ability of neurosteroids to potentiate responses to the allosteric activators etomidate, pentobarbital and propofol. Electrophysiological assays were conducted on rat α1β2γ2L GABAA receptors expressed
Samira Afrazi et al.
The Journal of steroid biochemistry and molecular biology, 139, 98-103 (2013-11-02)
Hyperglycemia plays a critical role in the development of diabetic neuropathy. Hyperglycemia induces oxidative stress in neurons, resulting in neuronal cell apoptosis and dysfunction. Anti-apoptotic properties of neurosteroids have been demonstrated in numerous cellular models of neurodegenerative studies. Here, the
Jonathan J Hirst et al.
The Journal of steroid biochemistry and molecular biology, 139, 144-153 (2013-05-15)
Neuroactive steroid concentrations are remarkably high in the foetal brain during late gestation. These concentrations are maintained by placental progesterone synthesis and the interaction of enzymes in the placenta and foetal brain. 5α-Pregnane-3α-ol-20-one (allopregnanolone) is a key neuroactive steroid during
Roberta D Brinton
Nature reviews. Endocrinology, 9(4), 241-250 (2013-02-27)
Regenerative therapeutics hold the promise of self-renewal and repair. Ageing and age-associated neurodegenerative diseases are marked by a decline in self-renewal and repair, but a capacity for regeneration is retained. The challenge faced by researchers developing molecular therapeutics to promote
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