ChemicalBook Product Catalog Pharmaceutical intermediates Bulk Drug Intermediates Allopregnanolone

Allopregnanolone

Product NameAllopregnanolone
CAS516-54-1
MFC21H34O2
MW318.49
EINECS687-782-2
MOL File516-54-1.mol

Chemical Properties

Melting point	176-178°
alpha	D +87.7° (abs alc)
Boiling point	431.2±18.0 °C(Predicted)
Density	1.053±0.06 g/cm3(Predicted)
storage temp.	Store at RT
solubility	chloroform: 20 mg/mL, clear, colorless
pka	15.12±0.70(Predicted)
form	White solid
color	white
Merck	13,272
BRN	3211363
Stability	Stable for 2 years as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
InChI	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+/s3
InChIKey	AURFZBICLPNKBZ-SYBPFIFISA-N
SMILES	[C@]12([H])CC[C@]3(C)[C@H](CC[C@@]3([H])[C@]1([H])CC[C@@]1([H])C[C@H](O)CC[C@]21C)C(=O)C \|&1:0,4,6,9,11,15,18,22,r\|
CAS DataBase Reference	516-54-1(CAS DataBase Reference)

Safety Information

Safety Statements	22-24/25
WGK Germany	3
RTECS	TU4383000
F	10

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

Allopregnanolone is an endogenous inhibitory pregnane neurosteroid that is synthesized from progesterone . It acts as a positive allosteric modulator of GABA_A receptors at nM concentrations (exhibiting the greatest potentiation at isoforms containing δ subunits) and of GABA_C receptors at μM concentrations. Allopregnanolone displays effects similar to other GABA_A receptor potentiators such as benzodiazepines, including potent anticonvulsant, anxiolytic, and sedative activity.

Uses

(3α)-Allopregnanolone acts as a GABAA receptor positive allosteric modulator. (3α)-Allopregnanolone is a metabolite of Progesterone (P755900). (3α)-Allopregnanolone is a neuroactive steroid present in the blood and also the brain.

Definition

ChEBI: Brexanolone is a 3-hydroxy-5alpha-pregnan-20-one in which the hydroxy group at position 3 has alpha-configuration. It is a metabolite of the sex hormone progesterone and used for the treatment of postpartum depression in women. It has a role as a human metabolite, an antidepressant, a GABA modulator, an intravenous anaesthetic and a sedative.

Biological Activity

GABA A receptor positive allosteric modulator. Neuroactive steroid.

Synthesis

synthesis of Brexanolone
Brexanolone synthesis

storage

Room temperature

References

[1] MARIA LUISA BARBACCIA . Endogenous γ-aminobutyric acid (GABA)A receptor active neurosteroids and the sedative/hypnotic action of γ-hydroxybutyric acid (GHB): A study in GHB-S (sensitive) and GHB-R (resistant) rat lines[J]. Neuropharmacology, 2005, 49 1: Pages 48-58. DOI:10.1016/j.neuropharm.2005.01.026
[2] REDDY D S. Neurosteroids: endogenous role in the human brain and therapeutic potentials.[J]. Progress in brain research, 2010, 186: 113-137. DOI:10.1016/b978-0-444-53630-3.00008-7
[3] ARIELA FRIEDER. Pharmacotherapy of Postpartum Depression: Current Approaches and Novel Drug Development.[J]. CNS drugs, 2019, 33 3: 265-282. DOI:10.1007/s40263-019-00605-7
[4] IRINA BALAN. Endogenous Neurosteroid (3α,5α)3-Hydroxypregnan-20-one Inhibits Toll-like-4 Receptor Activation and Pro-inflammatory Signaling in Macrophages and Brain.[J]. Scientific Reports, 2019: 1220. DOI:10.1038/s41598-018-37409-6
[5] YI CHANG. Neurosteroid allopregnanolone inhibits glutamate release from rat cerebrocortical nerve terminals.[J]. Synapse, 2019, 73 3: e22076. DOI:10.1002/syn.22076
[6] INJA CHO. Increased Superoxide Dismutase 2 by Allopregnanolone Ameliorates ROS-Mediated Neuronal Death in Mice with Pilocarpine-Induced Status Epilepticus[J]. Neurochemical Research, 2018, 43 7: 1464-1475. DOI:10.1007/s11064-018-2561-4