ChemicalBook > CAS DataBase List > GANAXOLONE

GANAXOLONE

Product Name: GANAXOLONE
CAS No.: 38398-32-2
Chemical Name: GANAXOLONE
Synonyms: GANAXOLONE;Fampridine Impurity 80;5α-PREGNAN-3β-METHYL-3α-;Noradrenaline Impurity 69;5α-PREGNAN-3β-METHYL-3α-OL-20-ONE;3α-hydroxy-3β-methyl-5α-pregnan-20-one;(3α,5α)-3-Hydroxy-3-methylpregnan-20-one;(3α,5α)-3-Hydroxy-3-methyl-pregnan-20-one;Pregnan-20-one, 3-hydroxy-3-methyl-, (3α,5α)-;1-((3R,5S,8R,9S,10S,13S,14S,17S)-3-Hydroxy-3,10,13-trimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone
CBNumber: CB8498146
Molecular Formula: C22H36O2
Formula Weight: 332.52
MOL File: 38398-32-2.mol

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GANAXOLONE Property

Melting point:: 190-192°
alpha: D +103°
Boiling point:: 434.8±18.0 °C(Predicted)
Density: 1.036±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMSO: ~4.2 mg/mL
form: solid
pka: 15.18±0.70(Predicted)
color: white
InChI: InChI=1/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+/s3
InChIKey: PGTVWKLGGCQMBR-TVQBYSQTNA-N
SMILES: [C@@]12([H])CC[C@@]3([H])C[C@@](O)(C)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C(CC[C@@]21[H])C(=O)C |&1:0,4,7,12,14,18,23,r|

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Safety

Safety Statements: 22-24/25
WGK Germany: 3
RTECS: TU4384700

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Warning

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: G7795
Product name: Ganaxolone
Purity: solid
Packaging: 5mg
Price: $202
Updated: 2025/07/31

Sigma-Aldrich

Product number: G7795
Product name: Ganaxolone
Purity: solid
Packaging: 25mg
Price: $696
Updated: 2025/07/31

Cayman Chemical

Product number: 20919
Product name: Ganaxolone
Purity: ≥98%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 20919
Product name: Ganaxolone
Purity: ≥98%
Packaging: 5mg
Price: $109
Updated: 2024/03/01

Cayman Chemical

Product number: 20919
Product name: Ganaxolone
Purity: ≥98%
Packaging: 10mg
Price: $153
Updated: 2024/03/01

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GANAXOLONE Chemical Properties,Usage,Production

Description

Ganaxolone is a 3β-methylated synthetic analog of the neurosteroid allopregnanolone that allosterically enhances GABA_A receptor current. At nanomolar concentrations, it can potentiate GABA-evoked currents at GABA_A receptor complexes containing α₁, α₂, α₃, β₂, and γ_2L subunits expressed in Xenopus oocytes. Ganaxolone has been shown to have a broad range of antiseizure activity in animal epilepsy models and human clinical trials.

Uses

Treatment of epilepsy and migraine.

Uses

Ganaxolone, is synthetic neuroactive steroid, which possess sedative, anxiolytic, and anticonvulsant properties. It is also a potent and selective positive allosteric modulator of GABAA receptors. It is also shown to be used for the treatment of epilepsy.

Definition

ChEBI: Ganaxolone is a corticosteroid hormone.

Application

Ganaxolone (marketed as Ztalmy) is a first-in-class neuroactive steroid that acts as a positive modulator of gamma-aminobutyric acid (GABA) A receptors for the treatment of seizures associated with cyclooxygenase-dependent kinase-like 5 (CDKL5) deficiency (CDD).

Biological Activity

Potent positive allosteric modulator of GABA A receptors. Enhances GABA-evoked chloride currents in Xenopus oocytes expressing GABA A receptors (EC 50 values are 94, 122 and 213 nM for α 2 β 1 γ 2 L , α 3 β 1 γ 2 L and α 1 β 1 γ 2 L receptors respectively). Exerts anticonvulsive effects in a broad range of animal seizure models.

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.

Mechanism of action

Ganaxolone works by positively modulating GABAA receptors, the major inhibitory neurotransmitter receptors in the central nervous system. This modulatory effect helps reduce the frequency and severity of seizures associated with CDD.

Synthesis

The synthesis begins with protection of the keto functionality in the natural steroid pregnenolone 10.1. Using acid catalysis, reaction with boiling ethylene glycol in toluene forms the acetal 10.2 in 88% yield. Oxidation of 10.2 to form the ketone 10.3 has been accomplished by a variety of methods, including Swern, Dess-Martin, and TPAP conditions. The oxidation process depicted in Figure 3.1 demonstrates the formation of the ketone 10.3 using calcium hypochlorite and TEMPO. Next, methylation is accomplished by the addition of MeMgBr in the presence of lithium chloride and ferric chloride to afford the tertiary alcohol 10.4. Finally, removal of the acetal protecting group by treatment with iodine in dichloromethane and acetone affords ganaxolone 10 in 98% yield over the last two steps.

storage

+4°C

References

[1] R B CARTER. Characterization of the anticonvulsant properties of ganaxolone (CCD 1042; 3alpha-hydroxy-3beta-methyl-5alpha-pregnan-20-one), a selective, high-affinity, steroid modulator of the gamma-aminobutyric acid(A) receptor.[J]. Journal of Pharmacology and Experimental Therapeutics, 1997, 280 3: 1284-1295.

GANAXOLONE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from GANAXOLONE manufacturers

Shaanxi Dideu New Materials Co. Ltd

Product: GANAXOLONE 38398-32-2
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10000KGS
Release date: 2025-03-15

Career Henan Chemical Co

Product: GANAXOLONE 38398-32-2
Price: US $0.01/KG
Min. Order: 1KG
Purity: 98%; 99%
Supply Ability: 500g;1kg； 25kg
Release date: 2020-01-09

38398-32-2, GANAXOLONERelated Search:

Sofalcone GANAXOLONE

3α-hydroxy-3β-methyl-5α-pregnan-20-one

(3α,5α)-3-Hydroxy-3-methyl-pregnan-20-one

1-((3R,5S,8R,9S,10S,13S,14S,17S)-3-Hydroxy-3,10,13-trimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone

(3α,5α)-3-Hydroxy-3-methylpregnan-20-one

1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-3,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone

Pregnan-20-one, 3-hydroxy-3-methyl-, (3α,5α)-

5α-PREGNAN-3β-METHYL-3α-OL-20-ONE

1-[(Chemicalbook3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-3,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone

5α-PREGNAN-3β-METHYL-3α-

Fampridine Impurity 80

Noradrenaline Impurity 69

GANAXOLONE

38398-32-2