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G7795

Ganaxolone

Name: Ganaxolone
Brand: SIGMA

solid, ≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₃₆O₂

CAS Number:

38398-32-2

Molecular Weight:

332.52

NACRES:

NA.77

PubChem Substance ID:

24724496

UNSPSC Code:

12352200

MDL number:

MFCD00945298

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

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Properties

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)

Description

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 GABA_A 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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Articles

GABAA Receptors

We offer many products related to GABAA receptors for your research needs.

DISCOVER Bioactive Small Molecules for Neuroscience

Alteration of ethanol drinking in mice via modulation of the GABA(A) receptor with ganaxolone, finasteride, and gaboxadol.

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

Endogenous and synthetic neurosteroids in treatment of Niemann-Pick Type C disease.

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

Effect of ganaxolone and THIP on operant and limited-access ethanol self-administration.