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G7795

Sigma-Aldrich

Ganaxolone

≥98% (HPLC), solid

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C22H36O2
Número de CAS:
38398-32-2
Peso molecular:
332.52
MDL number:
MFCD00945298
UNSPSC Code:
12352200
PubChem Substance ID:
24724496
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: ≥2 mg/mL
H2O: insoluble

storage temp.

2-8°C

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

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

InChI key

PGTVWKLGGCQMBR-FLBATMFCSA-N

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)

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.

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.

Quality

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Rafal M Kaminski et al.
Epilepsia, 45(7), 864-867 (2004-07-03)
Low-frequency (6 Hz), long-duration (3 s) electrical stimulation in mice produces seizures characterized by immobility, focal clonus, and automatic behaviors reminiscent of human limbic epilepsy. Renewed interest has been expressed in this seizure model with the recognition that it is
Malika Robichaud et al.
The international journal of neuropsychopharmacology, 9(2), 191-200 (2005-09-22)
Accumulating evidence suggest a reciprocal interaction between neurosteroids, especially 5alpha-pregnan-3alpha-ol,20-one (3alpha,5alpha-THP, allopregnanolone), and the serotonergic (5-HT) system. Both 5-HT and neurosteroids seem to play an important role in the pathophysiology of major depression. We have previously shown that a 7-d
R B Carter et al.
The Journal of pharmacology and experimental therapeutics, 280(3), 1284-1295 (1997-03-01)
Ganaxolone (CCD 1042) is a 3beta-methyl-substituted analog of the endogenous neuroactive steroid 3alpha-hydroxy-5alpha-pregnan-20-one. Ganaxolone inhibited binding of the gamma-aminobutyric acid (GABA)A receptor-chloride channel ligand t-[35S]butylbicyclophosphorothionate (IC50 of 80 nM) and enhanced binding of the benzodiazepine site ligand [3H]flunitrazepam (EC50 of
D S Reddy et al.
The Journal of pharmacology and experimental therapeutics, 295(3), 1241-1248 (2000-11-18)
Ganaxolone (3alpha-hydroxy-3beta-methyl-5alpha-pregnane-20-one), an orally active synthetic analog of the neuroactive steroid allopregnanolone, is a positive allosteric modulator of gamma-aminobutyric acid(A) receptors with anticonvulsant properties. We sought to determine whether tolerance occurs to the anticonvulsant activity of ganaxolone in the pentylenetetrazol
Nancy Foldvary-Schaefer et al.
Neurology, 61(6 Suppl 2), S2-15 (2003-09-25)
In women with epilepsy, seizures can be influenced by variations in sex hormone secretion during the menstrual cycle. The proconvulsant effects of estrogen have been demonstrated in both animals and humans, whereas progesterone has been found to have anticonvulsant properties.
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