Allopregnanolone

Alias: 5α-pregnan-3α-ol-20-one or 3α,5α-tetrahydroprogesterone (3α,5α-THP), or SAGE-547, Brexanolone, and Allotetrahydroprogesterone;SAGE-547;SGE102;SAGE547;SGE-102;SAGE 547; SGE 102; zulresso
Cat No.:V2878 Purity: ≥98%
Allopregnanolone [5α-pregnan-3α-ol-20-one or 3α,5α-tetrahydroprogesterone (3α,5α-THP), or SAGE-547, Brexanolone, zulresso and Allotetrahydroprogesterone] is a progesterone metabolite that serves as an allosteric modulator of theGABA (γ-aminobutyric acid) receptor.
Allopregnanolone Chemical Structure CAS No.: 516-54-1
Product category: GABA Receptor
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Purity: ≥98%

Product Description

Allopregnanolone [5α-pregnan-3α-ol-20-one or 3α,5α-tetrahydroprogesterone (3α,5α-THP), or SAGE-547, Brexanolone, zulresso and Allotetrahydroprogesterone] is a progesterone metabolite that serves as an allosteric modulator of the GABA (γ-aminobutyric acid) receptor. It has the potential for the treatment of Alzheimer’s Disease, epilepsy and depression. Allopregnanolone is an endogenous inhibitory pregnane neurosteroid that is synthesized from progesterone. Allopregnanolone has effects similar to those of other positive allosteric modulators of the GABA action at GABAA receptor such as the benzodiazepines, including anxiolytic, sedative, and anticonvulsant activity. Endogenously produced allopregnanolone exerts a pivotal neurophysiological role by fine-tuning of GABAA receptor and modulating the action of several positive allosteric modulators and agonists at GABAA receptor.

Biological Activity I Assay Protocols (From Reference)
ln Vitro

In vitro activity: Allopregnanolone, also known as 5α-pregnan-3α-ol-20-one or 3α,5α-tetrahydroprogesterone (3α,5α-THP), or SAGE-547, Brexanolone, and Allotetrahydroprogesterone, is a progesterone metabolite that serves as an allosteric modulator of the GABA (γ-aminobutyric acid) receptor. It has the potential for the treatment of epilepsy and depression. Allopregnanolone is an endogenous inhibitory pregnane neurosteroid that is synthesized from progesterone. Allopregnanolone has effects similar to those of other positive allosteric modulators of the GABA action at GABAA receptor such as the benzodiazepines, including anxiolytic, sedative, and anticonvulsant activity. Endogenously produced allopregnanolone exerts a pivotal neurophysiological role by fine-tuning of GABAA receptor and modulating the action of several positive allosteric modulators and agonists at GABAA receptor. Allopregnanolone induces a significant increase in proliferation of neuroprogenitor cells derived from the rat hippocampus and human neural stem cells derived from the cerebral cortex in a dose-dependent manner. Allopregnanolone increases the expression of genes that promote mitosis and inhibits the expression of genes that repress cell proliferation. Its biosynthesis begins with progesterone, which is converted to dihydroprogesterone by the enzyme 5α-DHP and after that, the enzyme 3α-HSOR catalyses the reduction of dihydroprogesterone toward allopregnanolone.


Cell Assay: Allopregnanolone induces a significant increase in proliferation of neuroprogenitor cells derived from the rat hippocampus and human neural stem cells derived from the cerebral cortex in a dose-dependent manner. Allopregnanolone increases the expression of genes that promote mitosis and inhibits the expression of genes that repress cell proliferation. Its biosynthesis begins with progesterone, which is converted to dihydroprogesterone by the enzyme 5α-DHP and after that, the enzyme 3α-HSOR catalyses the reduction of dihydroprogesterone toward allopregnanolone.

ln Vivo
Allopregnanolone increases both the K+-evoked [3H]-glutamate and [3H]-GABA release in P rats. The neurosteroid also increases the basal release of [3H]-glutamate in VO rats in an effect that is dependent on the modulation of NMDA receptors as is reverted by Mg2+. At therapeutic doses by either subcutaneous or intravenous routes, allopregnanolone mouse plasma levels range between 34-51ng/mL by 30min. Allopregnanolone-induced neurogenesis correlates with restoration of learning and memory function in a mouse model of Alzheimers disease and is comparably efficacious in aged normal mice.
Animal Protocol
Allopregnanolone is dissolved in 20%w/v HBCD solution at 2.5 mg/mL by brief sonication and is subcutaneously (SC) injected to mice at 0.5, 1, and 10 mg/kg.
Mice and rats
References
2005 May 11;25(19):4706-18;2015 Jun 3;10(6):e0128313;2013 Jul 23;243:64-75.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H34O2
Molecular Weight
318.49
CAS #
516-54-1
Related CAS #
516-54-1;
SMILES
O=C(C)[C@H]1CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C
Synonyms
5α-pregnan-3α-ol-20-one or 3α,5α-tetrahydroprogesterone (3α,5α-THP), or SAGE-547, Brexanolone, and Allotetrahydroprogesterone;SAGE-547;SGE102;SAGE547;SGE-102;SAGE 547; SGE 102; zulresso
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 10 mM
Water:<1 mg/mL
Ethanol:<1 mg/mL
Solubility (In Vivo)
CC([C@H]1CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O
 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.1398 mL 15.6991 mL 31.3982 mL
5 mM 0.6280 mL 3.1398 mL 6.2796 mL
10 mM 0.3140 mL 1.5699 mL 3.1398 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

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Biological Data
  • Allopregnanolone


    Rabbit plasma and brain concentration-time profiles of allopregnanolone following intravenous (IV) bolus or transdermal (TD) administration.2015 Jun 3;10(6):e0128313.

  • Allopregnanolone


    Mouse plasma and brain concentration-time profiles of allopregnanolone following intravenous (IV), subcutaneous (SC) and transdermal (TD) administration.2015 Jun 3;10(6):e0128313.

  • Allopregnanolone


    Subcutaneous Allo increased BrdU incorporation and PCNA protein expression in male mouse AD model.2015 Jun 3;10(6):e0128313.

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