Ganaxolone

Base Information

• Chemical Name: Ganaxolone
• CAS No.: 38398-32-2
• Molecular Formula: C22H36 O2
• Molecular Weight: 332.52
• European Community (EC) Number: 685-364-4
• UNII: 98WI44OHIQ
• DSSTox Substance ID: DTXSID6046503
• Nikkaji Number: J805.191G
• Wikipedia: Ganaxolone
• Wikidata: Q3758034
• NCI Thesaurus Code: C72793
• RXCUI: 2604689
• Metabolomics Workbench ID: 149389
• ChEMBL ID: CHEMBL1568698
• Mol file: 38398-32-2.mol

Synonyms:3alpha-hydroxy-3beta-methyl-5alpha-pregnan-20-one;CCD 1042;CCD-1042;ganaxolone;Ztalmy

Chemical Property of Ganaxolone

Chemical Property:

• Vapor Pressure: 2.19E-09mmHg at 25°C
• Melting Point: 190-192°
• Boiling Point: 434.8°Cat760mmHg
• PKA: 15.18±0.70(Predicted)
• Flash Point: 185.4°C
• PSA: 37.30000
• Density: 1.036g/cm³
• LogP: 4.98530
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ~4.2 mg/mL
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 332.271530387
• Heavy Atom Count: 24
• Complexity: 542

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ganaxolone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)(C)O)C)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@@](C4)(C)O)C)C
• Recent ClinicalTrials: A Clinical Trial of Intravenous (IV) Ganaxolone in Women With Postpartum Depression
• Recent EU Clinical Trials: A double-blind, randomized, placebo-controlled trial of adjunctive ganaxolone treatment in female children with protocadherin 19 (PCDH19)-related epilepsy followed by long-term open-label treatment
• 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. 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.

Technology Process of Ganaxolone

There total 16 articles about Ganaxolone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

dihydroprogesterone (566-65-4) + methylmagnesium chloride (676-58-4) → ganaxolone (38398-32-2)

Guidance literature:

methylmagnesium chloride; With iron(III) chloride; lithium chloride; In tetrahydrofuran; at -35 ℃;

dihydroprogesterone; In tetrahydrofuran; at -35 - -18 ℃; for 3h;

With hydrogenchloride; water; In tetrahydrofuran; at 25 ℃; Product distribution / selectivity;

Reference yield: 81.0%

dihydroprogesterone (566-65-4) + methylmagnesium bromide (75-16-1) → ganaxolone (38398-32-2)

Guidance literature:

methylmagnesium bromide; With iron(III) chloride; lithium chloride; In tetrahydrofuran; diethyl ether; at -35 - -30 ℃; for 0.5h;

dihydroprogesterone; In tetrahydrofuran; diethyl ether; at -20 - -15 ℃; for 2h;

Reference yield: 51.0%

1-((3R,5S,8R,9S,10S,13S,14S,17S)-3-Hydroxy-3-iodomethyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone (162882-87-3) → ganaxolone (38398-32-2)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In tetrahydrofuran; methanol; for 18h;

DOI:10.1021/jm960021x

upstream raw materials:

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

20,20-ethylenedioxy-3β-methyl-5α-pregnan-3α-ol

dihydroprogesterone

1-((2’R,8R,10S,13S,14S,17S)-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-3,2’-oxiran]-17-yl)ethanone

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR TREATING CNS DISORDERS". . . Retrieved 2016/05/24.
• 2、 -. "METHOD FOR MAKING 3α-HYDROXY, 3β- METHYL-5α-PREGNAN-20-ONE (GANAXOLONE)". Page/Page column 12. . Retrieved 2011/02/24.