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Merck
CN

G7795

Ganaxolone

≥98% (HPLC), solid

别名:

3α-Hydroxy-3β-methyl-5α-pregnan-20-one, CCD 1042

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关于此项目

经验公式（希尔记法）:
C22H36O2
化学文摘社编号:
38398-32-2
分子量:
332.52
NACRES:
NA.77
PubChem Substance ID:
24724496
UNSPSC Code:
12352200
MDL number:
MFCD00945298

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InChI

1S/C22H36O2/c1-14(23)17-7-8-18-16-6-5-15-13-20(2,24)11-12-21(15,3)19(16)9-10-22(17,18)4/h15-19,24H,5-13H2,1-4H3/t15-,16-,17+,18-,19-,20+,21-,22+/m0/s1

SMILES string

[H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H](C(C)=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC[C@@](C)(O)C2

InChI key

PGTVWKLGGCQMBR-FLBATMFCSA-N

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: ≥2 mg/mL, H2O: insoluble

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562), GABRD(2563), GABRE(2564), GABRG1(2565), GABRG2(2566), GABRG3(2567), GABRP(2568), GABRQ(55879)
mouse ... Gabrg2(14406)

相关类别

Biochem/physiol Actions

Ganaxolone (3alpha-hydroxy-3beta-methyl-5alpha-pregnane-20-one) is a positive allosteric modulator of the GABAA receptor subtype; synthetic analog of the endogenous neurosteroid allopregnanolone; effective against chemically induced seizures in rats and mice. Ganaxolone is an orally active analog of allopregnanolone that is not converted to the hormonally active 3-keto form. The enhanced anticonvulsant potency of ganaxolone after neurosteroid withdrawal supports the use of ganaxolone as a specific treatment for perimenstrual catamenial epilepsy.
Positive allosteric modulator of the GABAA receptor subtype; synthetic analog of the endogenous neurosteroid allopregnanolone; effective against chemically induced seizures in rats and mice.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GABAA Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Analysis Note

The product is pure based on elemental analysis, NMR, MS, optical rotation and melting point.

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000051177
0000051177
0000212131
0000212131
0000212130

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Delia Belelli et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 23(31), 10013-10020 (2003-11-07)
Neurosteroids typified by 5alpha-pregnan-3alpha-ol-20-one (5alpha3alpha) have emerged as the most potent endogenous positive modulators of the GABAA receptor, the principal mediator of fast inhibitory transmission within the CNS. Neurosteroids can be synthesized de novo in the brain in levels sufficient
Rita Citraro et al.
Neuropharmacology, 50(8), 1059-1071 (2006-04-25)
Neurosteroids are synthesized in the brain and have been demonstrated to modulate various cerebral functions. Allopregnanolone (3alpha-hydroxy-5alpha-pregnan-20-one), a naturally occurring neurosteroid, and ganaxolone (3alpha-hydroxy-3beta-methyl-5alpha-pregnan-20-one), a synthetic derivative, are two neurosteroids acting as positive allosteric modulators of the GABA(A) receptor complex
Synthia H Mellon et al.
Brain research reviews, 57(2), 410-420 (2007-07-17)
The functions for neurosteroids during development and in response to nervous system injury are beginning to be identified. We focused on a mouse model in which we believed neurosteroid production would be altered, and which had a neurodegenerative phenotype. Niemann-Pick
Marcia J Ramaker et al.
Alcoholism, clinical and experimental research, 35(11), 1994-2007 (2011-06-09)
Neurosteroids and other γ-aminobutyric acid(A) (GABA(A) ) receptor-modulating compounds have been shown to affect ethanol intake, although their mechanism remains unclear. This study examined how patterns of 24-hour ethanol drinking in mice were altered with the synthetic GABAergic neurosteroid ganaxolone
Doodipala Samba Reddy
Progress in brain research, 186, 113-137 (2010-11-26)
This chapter provides an overview of neurosteroids, especially their impact on the brain, sex differences and their therapeutic potentials. Neurosteroids are synthesized within the brain and rapidly modulate neuronal excitability. They are classified as pregnane neurosteroids, such as allopregnanolone and
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