-Oxiracetam (ISF2522) Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C6H10N2O3 |
| Molecular Weight | 158.15 |
| Exact Mass | 158.069 |
| CAS # | 88929-35-5 |
| Related CAS # | (R)-Oxiracetam;68252-28-8;Oxiracetam;62613-82-5 |
| PubChem CID | 6603951 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 494.6±40.0 °C at 760 mmHg |
| Flash Point | 252.9±27.3 °C |
| Vapour Pressure | 0.0±2.9 mmHg at 25°C |
| Index of Refraction | 1.570 |
| LogP | -2.48 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 11 |
| Complexity | 192 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | C(N1C(=O)C[C@H](O)C1)C(=O)N |
| InChi Key | IHLAQQPQKRMGSS-BYPYZUCNSA-N |
| InChi Code | InChI=1S/C6H10N2O3/c7-5(10)3-8-2-4(9)1-6(8)11/h4,9H,1-3H2,(H2,7,10)/t4-/m0/s1 |
| Chemical Name | 2-[(4S)-4-hydroxy-2-oxopyrrolidin-1-yl]acetamide |
| Synonyms | S-Oxiracetam (S)-ISF-2522 (S)-Oxiracetam |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | (S)-Oxiracetam (1, 10, 100 μM; 24 h) stimulates PI3K/Akt/GSK3β signaling that is reliant on α7 nAChR and shields the shell of fetal rat primary cortical neurons from OGD/R injury[1]. [1] |
| ln Vivo | (S)-Oxiracetam (IV once daily for seven days; 0.12, 0.24, and 0.48 g/kg) considerably minimizes the extent of the infarct and mildly modifies Sprague behavior-MACO/R model in solution caused by Dawson simulation Inhibitory and dysfunctional When administered intraperitoneally 60 minutes before to apomorphine, salted remoxipride (0.1-100 μM/kg) prevents vomiting in dogs and apomorphine-induced behavior in rats [1]. In striatal and extrastriatal areas, (S)-Remopride hydrochloride (0.1–10 mg/kg; intraperitoneally; 30 minutes prior to apomorphine) displaces [3H]spiperone [1]. |
| Cell Assay |
Cell Viability Assay[1] Cell Types: fetal mouse primary cortical neurons Tested Concentrations: 1, 10, 100 μM Incubation Duration: 24 hrs (hours) Experimental Results: Compared with OGD/R, the survival rate of cortical neurons was increased (58.82%, 64.82% respectively and 79.15%) groups. Cytotoxicity assay [1] Cell Types: fetal mouse primary cortical neurons Tested Concentrations: 1, 10, 100 μM Incubation Duration: 24 h Experimental Results: LDH activity diminished to 567.59 U/L, 484.89 U/L and 428.15 U/ L compared with the OGD/R group (725.22 U/L), were μM, 10 μM and 100 μM respectively. Apoptosis analysis [1] Cell Types: fetal mouse primary cortical neurons Tested Concentrations: 1, 10, 100 μM Incubation Duration: 24 hrs (hours) Experimental Results: The apoptosis rate of cortical neurons dependent on α7 nAChR was diminished (34.48%, 16.15% and 10.05%) ) compared with the OGD/R group. Western Blot Analysis [1] Cell Types: fetal mouse primary cortical neurons Tested Concentrations: 1, 10, 100 μM Incubation Duration: 24 h Experimental Results: α7 nAChR expression increased (1 μM increased by 46.95%, 58 |
| Animal Protocol |
Animal/Disease Models: Swiss albino mouse scopolamine-induced amnesia model [1]. Doses: 0.12, 0.24, 0.48 g/kg, one time/day for 7 days Route of Administration: intravenous (iv) (iv)injection Experimental Results: Compared with the sham operation group, the infarct area of rats was diminished to 26.04 ± 1.07%, 21.66 ± 2.27% , 12.26 ± 5.59% group were 0.12 g/kg, 0.24 g/kg, and 0.48 g/kg respectively. Neurologic scores improved compared with the MCAO/R group. Neurons were protected from apoptosis compared with the sham group. Compared with the MCAO/R group, the phosphorylated expression of α7 nAChR, as well as PI3K, Akt and GSK3β was increased. GSH-PX concentrations increased (189.54 units, 193.07 units, and 203.98 units, respectively). |
| References |
[1]. S-oxiracetam ameliorates ischemic stroke induced neuronal apoptosis through up-regulating α7 nAChR and PI3K / Akt / GSK3β signal pathway in rats. Neurochem Int. 2018 May;115:50-60. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~250 mg/mL (~1580.68 mM) |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.3231 mL | 31.6156 mL | 63.2311 mL | |
| 5 mM | 1.2646 mL | 6.3231 mL | 12.6462 mL | |
| 10 mM | 0.6323 mL | 3.1616 mL | 6.3231 mL |