(1S,2S,5R,7S,10S,11S,14S,15S)-14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-17-one

• ChemBase ID: 105628
• Molecular Formular: C21H32O3
• Molecular Mass: 332.47698
• Monoisotopic Mass: 332.23514488
• SMILES: O=C1[C@H]2[C@H]([C@@H]3CC[C@H](C(=O)C)[C@@]3(C)C1)CC[C@H]1C[C@H](O)CC[C@]21C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2C(=O)C[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
• InChI: InChI=1S/C21H32O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h13-17,19,23H,4-11H2,1-3H3/t13-,14+,15-,16+,17-,19+,20-,21+/m0/s1
• InChIKey: DUHUCHOQIDJXAT-OLVMNOGESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7S,10S,11S,14S,15S)-14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-17-one; (1S,2S,5R,7S,10S,11S,14S,15S)-14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one
• IUPAC Traditional name: alfaxalone
• Synonyms: 3-Hydroxy-5α-pregnane-11,20-dione; Alfaxalone; 5α-Pregnan-3α-ol-11,20-dione; 3α-Hydroxy-5α-pregnane-11,20-dione; αXALONE

Database IDs

• CAS Number: 23930-19-0
• MDL Number: MFCD00083468
• PubChem SID: 162092653; 24278637
• PubChem CID: 104845

CALCULATED PROPERTIES

• Acid pKa: 18.296383
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.0636873
• LogD (pH = 7.4): 3.0636873
• Log P: 3.0636873
• Molar Refractivity: 93.574 cm^3
• Polarizability: 37.255684 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform: ≥5 mg/mL, clear, colorless
• Apperance: white powder

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: TU4157800
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• Safety Statements: 22-36
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562), GABRG2(2566)

Product Information

• Purity: ≥98% (TLC)

DETAILS

MP Biomedicals - 02193579

A neurosteroid which acts upon the GABA_A receptor.

Sigma Aldrich - P5052

Biochem/physiol Actions
Synthetic steroid compound alphaxalone (AFX) - 5α-Pregnan-3α-ol-11,20-dione- is a neurosteroid that directly activates and potentiates GABAA receptor-activated membrane current (IGABA). It acts as a positive allosteric modulator of the GABAA receptor; anesthetic. The alpha subunit subtype of GABAA determines the efficacy, but not the potency, of AFX neuroactive steroid to potentiate IGABA.

REFERENCES

• Turner, et al., J. Pharmacol. Exp. Ther. , 248 : 960, (1989).