Related articles - How to synthesize Brexanolone？
- Developed by Sage Therapeutics, brexanolone was approved by the USFDA as a first-in-class treatment for PPD in adult women.
- Jan 8，2024
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| | Allopregnanolone Basic information |
| Product Name: | Allopregnanolone | | Synonyms: | 1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone;3-A-5-A-TETRAHYDROPROGESTERONE;3-alpha,5-alpha-pregnanolone;3α-OH-DHP;Allopregnan-3a-ol-20-one;(3α)-Allopregnanolone;3α,5α-Tetrahydroprogesterone;3α,5α-THP | | CAS: | 516-54-1 | | MF: | C21H34O2 | | MW: | 318.49 | | EINECS: | | | Product Categories: | Intermediates & Fine Chemicals;Metabolites & Impurities;Neurochemicals;Pharmaceuticals;Steroids;API | | Mol File: | 516-54-1.mol |  |
| | 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 | | 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. | | InChIKey | AURFZBICLPNKBZ-SYBPFIFISA-N | | CAS DataBase Reference | 516-54-1(CAS DataBase Reference) |
| Safety Statements | 22-24/25 | | WGK Germany | 3 | | RTECS | TU4383000 | | F | 10 |
| | 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 GABAA receptors at nM concentrations (exhibiting the greatest potentiation at isoforms containing δ subunits) and of GABAC receptors at μM concentrations. Allopregnanolone displays effects similar to other GABAA 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 Preparation Products And Raw materials |
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