516-54-1 Usage
Description
ALLOPREGNAN-3ALPHA-OL-20-ONE, also known as Allopregnanolone, is an endogenous inhibitory pregnane neurosteroid synthesized from progesterone. It acts as a positive allosteric modulator of GABAA receptors at nM concentrations, particularly potentiating isoforms containing δ subunits, and of GABAC receptors at μM concentrations. Allopregnanolone exhibits effects similar to other GABAA receptor potentiators, such as benzodiazepines, including potent anticonvulsant, anxiolytic, and sedative activity. It is a neuroactive steroid present in both the blood and the brain.
Uses
Used in Pharmaceutical Industry:
ALLOPREGNAN-3ALPHA-OL-20-ONE is used as a therapeutic agent for its anticonvulsant, anxiolytic, and sedative properties. Its ability to modulate GABAA and GABAC receptors makes it a promising candidate for the treatment of various neurological and psychiatric disorders.
Used in Neurological Applications:
ALLOPREGNAN-3ALPHA-OL-20-ONE is used as a neuroactive steroid for its potent anticonvulsant, anxiolytic, and sedative effects. It helps in the management of seizure disorders, anxiety, and sleep-related issues by enhancing the inhibitory action of GABA in the brain.
Used in Research and Development:
ALLOPREGNAN-3ALPHA-OL-20-ONE is used as a research compound to study the role of neurosteroids in the modulation of GABAergic signaling and their potential applications in the development of new therapeutic strategies for neurological and psychiatric conditions.
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
Check Digit Verification of cas no
The CAS Registry Mumber 516-54-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 6 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 516-54:
(5*5)+(4*1)+(3*6)+(2*5)+(1*4)=61
61 % 10 = 1
So 516-54-1 is a valid CAS Registry Number.
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+/m0/s1
516-54-1Relevant articles and documents
Fleischer,Whitman,Schwenk
, p. 79 (1938)
Stereospecific reduction of 5β-reduced steroids by human ketosteroid reductases of the AKR (aldo-keto reductase) superfamily: Role of AKR1C1-AKR1C4 in the metabolism of testosterone and progesterone via the 5β-reductase pathway
Jin, Yi,Mesaros, A. Clementina,Blair, Ian A.,Penning, Trevor M.
experimental part, p. 53 - 61 (2012/06/15)
Active sex hormones such as testosterone and progesterone are metabolized to tetrahydrosteroids in the liver to terminate hormone action. One main metabolic pathway, the 5β-pathway, involves 5β-steroid reductase (AKR1D1, where AKR refers to the aldo-keto reductase superfamily), which catalyses the reduction of the 4-ene structure, and ketosteroid reductases (AKR1C1-AKR1C4), which catalyse the subsequent reduction of the 3-oxo group. The activities of the four human AKR1C enzymes on 5β-dihydrotestosterone, 5β-pregnane-3,20-dione and 20α-hydroxy-5β-pregnan-3-one, the intermediate 5β-dihydrosteroids on the 5β-pathway of testosterone and progesterone metabolism, were investigated. Product characterization by liquid chromatography-MS revealed that the reduction of the 3-oxo group of the three steroids predominantly favoured the formation of the corresponding 3α-hydroxy steroids. The stereochemistry was explained by molecular docking. Kinetic properties of the enzymes identified AKR1C4 as the major enzyme responsible for the hepatic formation of 5β-tetrahydrosteroid of testosterone, but indicated differential routes and roles of human AKR1C for the hepatic formation of 5β-tetrahydrosteroids of progesterone. Comparison of the kinetics of the AKR1C1-AKR1C4-catalysed reactions with those of AKR1D1 suggested that the three intermediate 5β-dihydrosteroids derived from testosterone and progesterone are unlikely to accumulate in liver, and that the identities and levels of 5β-reduced metabolites formed in peripheral tissues will be governed by the local expression of AKR1D1 and AKR1C1-AKR1C3. The Authors Journal compilation 2011 Biochemical Society.
REGIOSELECTIVE REDUCTION OF POLYKETONES ON SILICA GEL SURFACE WITH BORANE-TRIMETHYLAMINE COMPLEX
Gohzu, Shun-ichi,Tada, Masahiro
, p. 61 - 64 (2007/10/02)
Steroidal diones and trione, bicyclic diones (7 and 8) and a tricyclic dione were adsorbed on silica gel and reduced with BH3*NMe3.The carbonyl groups at C-3 of the steroids, at C-4 of 7 and at C-3 of 8 were reduced regioselectively.The FT-IR spectra of 5α- and 5β-androstane-3,17-dione adsorbed on silica gel were measured.
