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
More
Less

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|
More
Less

Safety

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
More
Less

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
More
Less

GANAXOLONE Chemical Properties,Usage,Production

Description

Ganaxolone is a 3β-methylated synthetic analog of the neurosteroid allopregnanolone that allosterically enhances GABAA receptor current. At nanomolar concentrations, it can potentiate GABA-evoked currents at GABAA receptor complexes containing α1, α2, α3, β2, and γ2L 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

More
Less

GANAXOLONE Suppliers

China 62 Germany 1 India 4 Japan 1 South Korea 1 Switzerland 1 United Kingdom 4 United States 9 Global 83
Hunan Well Medicine Synthesis Technology Co., Ltd
Tel
0731-85589467; 13574065797
Email
3877753494@qq.com
Country
China
ProdList
36
Advantage
58
Bayee Biotech (Anqing) Co., Ltd.
Tel
0556-5032306 18917961636
Email
wtx@bayeebio.com
Country
China
ProdList
239
Advantage
61
Taizhou Nanfeng Pharmaceutical Research Institute
Tel
nanfengdrug@163.com; 18616377689
Email
nanfengdrug@163.com
Country
China
ProdList
20009
Advantage
58
J & K SCIENTIFIC LTD.
Tel
18210857532; 18210857532
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15838
Advantage
69
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14101
Advantage
59
WUHAN SUN-SHINE BIO-TECHNOLOGY Co., Ltd.
Tel
17702719238 18971495150;
Email
sales@sun-shinechem.com
Country
China
ProdList
1077
Advantage
64
Nanjing Sunlida Biological Technology Co., Ltd.
Tel
025-57798810
Fax
025-57019371
Email
sales@sunlidabio.com
Country
China
ProdList
3239
Advantage
55
Hangzhou J&H Chemical Co., Ltd.
Tel
0571-87396432
Fax
0571-87396431
Email
sales@jhechem.com
Country
China
ProdList
14912
Advantage
59
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51395
Advantage
80
More
Less

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