1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,5,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]ethan-1-one

• ChemBase ID: 153874
• Molecular Formular: C22H36O2
• Molecular Mass: 332.52004
• Monoisotopic Mass: 332.27153039
• SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2CC[C@@H]2[C@@]1(CC[C@@](C2)(C)O)C)C
• Canonical SMILES: CC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)CC[C@@](C2)(C)O
• InChI: 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
• InChIKey: PGTVWKLGGCQMBR-FLBATMFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,5,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]ethan-1-one
• IUPAC Traditional name: ganaxolone
• Synonyms: 3α-Hydroxy-3β-methyl-5α-pregnan-20-one; CCD 1042; Ganaxolone

Database IDs

• CAS Number: 38398-32-2
• MDL Number: MFCD00945298
• PubChem SID: 162248013; 24724496
• PubChem CID: 6918305

CALCULATED PROPERTIES

• Acid pKa: 19.102476
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.2675147
• LogD (pH = 7.4): 4.2675147
• Log P: 4.2675147
• Molar Refractivity: 97.5449 cm^3
• Polarizability: 39.03014 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥2 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... GABRA1(2554)mouse ... Gabrg2(14406)

Product Information

• Purity: (The product is pure based on elemental analysis, NMR, MS, optical rotation and melting point.); ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H36O2

DETAILS

Sigma Aldrich - G7795

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.