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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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Certificates of Analysis (COA)

Lot/Batch Number

0000051177

0000212130

0000212131

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Effects of some neurosteroids injected into some brain areas of WAG/Rij rats, an animal model of generalized absence epilepsy.

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

The contraceptive agent Provera enhances GABA(A) receptor-mediated inhibitory neurotransmission in the rat hippocampus: evidence for endogenous neurosteroids?

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

Early postnatal ethanol intubation blunts GABA(A) receptor up-regulation and modifies 3alpha-hydroxy-5alpha-pregnan-20-one sensitivity in rat MS/DB neurons.

S H Hsiao et al.

Brain research. Developmental brain research, 130(1), 25-40 (2001-09-15)

Previously we found postnatal binge-like ethanol exposure using an artificial-rearing method in the rat delayed developmental up-regulation of GABA(A) receptors (GABA(A)Rs) in both medial septum/diagonal band (MS/DB) and cerebellar Purkinje neurons. In the present study, the impact of ethanol on

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