Allopregnanolone 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

form 

White solid

pka

15.12±0.70(Predicted)

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.

InChIKey

AURFZBICLPNKBZ-SYBPFIFISA-N

CAS DataBase Reference

516-54-1(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

TU4383000

F 

10

MSDS

• Language:English Provider:SigmaAldrich

Allopregnanolone 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.

storage

Room temperature

References

1) Belelli and Lambert (2005),?Neurosteroids: endogenous regulators of the GABA(A) receptor; Nat. Rev. Neurosci,,?6?565 2) Reddy?et al. (2010),?Neurosteroids: endogenous role in the human brain and therapeutic potentials; Prog. Brain Res.,?186?113 3) Frieder?et al. (2019),?Pharmacotherapy of Postpartum Depression: Current Approaches and Novel Drug Development; CNS Drugs,?33?265 4) Balan?et al.?(2019),?Endogenous Neurosteroid (3α,5α)3-Hydroxypregnan-20-one Inhibits Toll-like-4 Receptor Activation and Proinflammatory Signaling in Macrophages and Brain; Sci. Rep.,?9?1220 5) Chang?et al.?(2019),?Neurosteroid allopregnanolone inhibits glutamate release from rat cerebrocortical nerve terminals; Synapse,?73?e22076 6) Cho?et al.?(2018),?Increased Superoxide Dismutase 2 by Allopregnanolone Ameliorates ROS-Mediated Neuronal Death in Mice with Pilocarpine-Induced Status Epilepticus; Neurochem. Res.,?43?1464

Allopregnanolone(516-54-1)Related Product Information

• Allopregnanolone-[d5] (Solution)
• Allopregnanolone-[D5]
• Allopregnanolone
• Alphadolone
• Alfaxalone
• ALLOPREGNANOLONE(RG)
• 21-HYDROXYALLOPREGNANOLONE
• 5-ALPHA-PREGNAN-3-BETA, 17,21-TRIOL-11,20-DIONE
• ALLOTETRAHYDROCORTISOL
• ALLOTETRAHYDROCORTICOSTERONE
• 5-ALPHA-PREGNAN-3-ALPHA, 11-BETA, 17,21-TETROL-20-ONE 3,21-DIACETATE
• 5-ALPHA-PREGNAN-3-ALPHA, 17-DIOL-20-ONE
• ALLOTETRAHYDRO S
• 3alpha,21-dihydroxy-5alpha-pregnane-11,20-dione 21-acetate
• ALLOPREGNANOLONE ACETATE,3β-Hydroxy-5α-pregnan-20-one acetate, Allopregnanolone acetate
• 3β-Hydroxy-5α-pregnan-20-one, 3β-Hydroxy-5α-tetrahydroprogesterone, 5α-Dihydropregnenolone, Allopregnanolone, Isopregnanolone,3-beta-allopregnanolon
• 5-ALPHA-PREGNAN-3-ALPHA, 21-DIOL-20-ONE 3-ACETATE
• 5alpha-Pregnan-3alpha,11alpha-diol-20-one