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Purity: ≥98%
Oxiracetam (also known as ISF 2522), a novel cyclic derivative of gamma-aminobutyric acid (GABA) which acts as a positive allosteric modulator of the AMPA receptors, is widely used as a nootropic drug to improve memory and learning in patients with cognitive impairments. Oxiracetam (50 mg/kg i.p.) improves avoidance acquisition in BALB/c mice. Oxiracetam (100 mg/kg i.p.) reduces the scopolamine-induced amnesic effect and decrease in acetylcholine level in the cortex and hippocampus. Oxiracetam pretreatment (30 mg/kg) prevents social recognition deficits produced with trimethyltin in rats.
Oxiracetam (ISF 2522) is a nootropic agent belonging to the racetam family, chemically named 4-hydroxy-2-oxo-1-pyrrolidineacetamide with molecular formula C6H10N2O3 and molecular weight 158.16. Developed by ISF Italy in the 1970s, this drug is clinically used for treating cognitive impairments, particularly those of cerebrovascular origin and multi-infarct dementia. Oxiracetam is currently used as a racemic mixture containing both (S)-oxiracetam and (R)-oxiracetam enantiomers, with the principal pharmacological activity derived from (S)-oxiracetam.| Targets |
The mechanism of action of oxiracetam is not fully elucidated, but research indicates that it exerts its nootropic effects through multiple pathways. Oxiracetam is thought to directly influence energy metabolism in the brain, improving the energy supply status of brain cells. Specifically, (S)-oxiracetam can activate the α7 nicotinic acetylcholine receptor, subsequently activating the PI3K/Akt/GSK3β signaling pathway to inhibit neuronal apoptosis. Furthermore, oxiracetam possesses anti-inflammatory activity, inhibiting NLRP3 inflammasome activation and reducing the expression of inflammatory factors such as COX-2, caspase-1, and IL-1β, while increasing the expression of superoxide dismutase (SOD1, SOD2) to exert antioxidant effects.
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| ln Vitro |
In vitro activity: Oxiracetam (also known as ISF 2522), a cyclic derivative of gamma-aminobutyric acid (GABA), is used as a nootropic drug to improve memory and learning. In vitro studies demonstrate that oxiracetam exhibits neuroprotective and anti-inflammatory activities. Research shows that treatment with (S)-oxiracetam at concentrations of 1, 10, and 100 μM for 24 hours significantly protects fetal rat primary cortical neurons from oxygen-glucose deprivation/reoxygenation (OGD/R) injury and activates the PI3K/Akt/GSK3β signaling pathway in an α7 nAChR-dependent manner. Another study revealed that treatment with 100 nM oxiracetam in damaged SH-SY5Y cells increases SOD1 and SOD2 mRNA expression while decreasing mRNA and protein expression levels of COX-2, NLRP3, caspase-1, and IL-1β, along with reductions in intracellular reactive oxygen species production and apoptosis. Comparative studies of chiral oxiracetam indicate that both oxiracetam and (S)-oxiracetam exhibit good neuroprotective effects against primary neuronal damage induced by glutamate and calcium ions. |
| ln Vivo |
Oxiracetam (50 mg/kg i.p.) improves avoidance acquisition in BALB/c mice. Oxiracetam (100 mg/kg i.p.) reduces the scopolamine-induced amnesic effect and decrease in acetylcholine level in the cortex and hippocampus. Oxiracetam pretreatment (30 mg/kg) prevents social recognition deficits produced with trimethyltin in rats.
Oxiracetam demonstrates cognitive improvement and neuroprotective effects in various animal models. In the chronic cerebral hypoperfusion (2-VO) rat model, (S)-oxiracetam (100, 200 mg/kg) and racemic oxiracetam (400 mg/kg) significantly improve spatial learning and memory impairments, reduce astrocyte activation in the hippocampal CA1 region, increase cerebral blood flow, and regulate ATP metabolism, glutamine-glutamate cycling, and antioxidant levels in the cortex. Morris water maze and step-down tests also confirm that oxiracetam and (S)-oxiracetam improve cognitive function in 2-VO rats. In a traumatic brain injury mouse model, intraperitoneal administration of oxiracetam (30 mg/kg/day for 5 days) reduces cortical damaged lesions, brain edema, and the number of FJB-positive and TUNEL-positive cells, while improving cognitive function. In a middle cerebral artery occlusion/reperfusion (MCAO/R) rat model, (S)-oxiracetam (0.12, 0.24, 0.48 g/kg, intravenous injection once daily for 7 days) significantly reduces infarct size and ameliorates behavioral dysfunction. |
| Enzyme Assay |
In vitro mechanistic studies of oxiracetam are typically conducted at the cellular level, with few reports on cell-free enzyme/receptor binding assays. For determining binding affinity of oxiracetam to receptors or proteins, the following protocol can be used: Prepare serial dilutions of oxiracetam in DMSO or PBS, incubate with recombinant target proteins (e.g., α7 nAChR or PI3K-related proteins) in binding buffer (such as 50 mM HEPES, pH 7.4, 150 mM NaCl, 0.1% BSA, 0.01% Tween-20) for 30-60 minutes at room temperature. Measure binding affinity (Kd) using surface plasmon resonance (SPR) or micro-scale thermophoresis (MST). Radioligand binding assays using radiolabeled oxiracetam or its analogs for competition binding with membrane proteins can also be employed.
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| Cell Assay |
The in vitro cell assay protocol for oxiracetam is as follows: 1) Seed target cells (such as SH-SY5Y human neuroblastoma cells or rat primary cortical neurons) in culture plates and culture to appropriate density at 37°C with 5% CO₂. 2) Prepare oxiracetam working solutions, with common concentration ranges of 1-100 μM or 100 nM. 3) For neuroprotection experiments, pre-treat cells with oxiracetam for a period (e.g., 24 hours) before exposure to injury conditions (such as oxygen-glucose deprivation/reoxygenation, glutamate, or calcium ion stimulation). 4) Assess cell viability using MTT or CCK-8 assays. 5) Detect relevant protein expression (e.g., PI3K/Akt/GSK3β pathway proteins, COX-2, NLRP3, caspase-1, IL-1β) by Western blot, and measure mRNA expression levels by qPCR. 6) Assess apoptosis rate using flow cytometry or TUNEL staining.
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| Animal Protocol |
The typical in vivo animal assay protocol for oxiracetam is as follows: 1) Establish disease animal models, such as the chronic cerebral hypoperfusion (2-VO) rat model, traumatic brain injury mouse model, or middle cerebral artery occlusion/reperfusion (MCAO/R) rat model. 2) Randomly divide animals into model, vehicle control, positive control, and oxiracetam treatment groups (multiple doses), with 8-20 animals per group. 3) Administration routes: oral gavage (rats 100-400 mg/kg), intraperitoneal injection (mice 30 mg/kg/day), or intravenous injection (0.12-0.48 g/kg). 4) Treatment duration is typically 5 days to 2 weeks. 5) Assess learning and memory abilities using behavioral tests such as the Morris water maze and step-down test. 6) After euthanasia, collect brain tissue for histopathological analysis (e.g., Nissl staining, TUNEL staining, FJB staining), immunohistochemical detection (e.g., GFAP, Iba-1), and molecular biology assays.
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| ADME/Pharmacokinetics |
Pharmacokinetic studies of oxiracetam in rats and humans demonstrate good oral absorption characteristics. Following oral administration of 100, 200, and 400 mg/kg in rats, serum concentration-time curves fit an open one-compartment model, with absorption half-life (T1/2ka) of 0.11-0.36 hours, peak time (Tpeak) of 0.79-1.41 hours, and elimination half-life (T1/2ke) of 3.18-4.05 hours. Tissue distribution studies show that oxiracetam is widely distributed throughout various tissues 1 hour after administration, with tissue concentrations from high to low in heart, liver, kidney, brain, muscle, spleen, intestine, stomach, testis, fat, lung, and ovary. Oxiracetam is primarily excreted via urine, with approximately 80% of the administered dose excreted unchanged within 36 hours, and plasma protein binding is low at approximately 10.5%. In healthy volunteers receiving intravenous administration of 2000 mg oxiracetam, the elimination half-life is approximately 3.84 hours, with no significant accumulation observed after 7 days of consecutive dosing. (S)-Oxiracetam exhibits a higher absorption rate and slower elimination rate compared to the racemate.
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| Toxicity/Toxicokinetics |
Preclinical and clinical studies of oxiracetam demonstrate a favorable safety profile. Animal studies indicate that the substance is considered safe even when high doses are consumed over long periods. The median lethal dose in rats is relatively high, indicating a wide safety window. A recent large-scale Phase III clinical trial (n=590) in patients with traumatic brain injury showed no significant differences in the proportion of serious adverse events among the L-oxiracetam (4 g/day), oxiracetam (6 g/day), and placebo groups, with no significant safety concerns identified. Common adverse effects may include mild gastrointestinal discomfort or headache, but these are typically rare and tolerable. It should be noted that oxiracetam is currently for research use only and has not been approved by the US FDA for any medical use.
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| References |
[1]. Arch Int Pharmacodyn Ther.1985 May;275(1):86-92;
[2]. Pharmacol Biochem Behav.1987 Jul;27(3):491-5. |
| Additional Infomation |
Oxiracetam is an oxygen- and nitrogen-containing organic compound whose function is related to α-amino acids.
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| Molecular Formula |
C6H10N2O3
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| Molecular Weight |
158.16
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| Exact Mass |
158.069
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| Elemental Analysis |
C, 45.57; H, 6.37; N, 17.71; O, 30.35
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| CAS # |
62613-82-5
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| Related CAS # |
(S)-Oxiracetam;88929-35-5;(R)-Oxiracetam;68252-28-8
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| PubChem CID |
4626
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
494.6±40.0 °C at 760 mmHg
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| Melting Point |
165-168ºC
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| Flash Point |
252.9±27.3 °C
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| Vapour Pressure |
0.0±2.9 mmHg at 25°C
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| Index of Refraction |
1.570
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| LogP |
-2.48
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
11
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| Complexity |
192
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1C(CN(C1=O)CC(=O)N)O
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| InChi Key |
IHLAQQPQKRMGSS-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H10N2O3/c7-5(10)3-8-2-4(9)1-6(8)11/h4,9H,1-3H2,(H2,7,10)
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| Chemical Name |
4-Hydroxy-2-oxopyrrolidine-N-acetamide
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| Synonyms |
ISF 2522; ISF2522; oxiracetam; 62613-82-5; CGP 21690E; Oxiracetamum; ISF-2522;Neuractiv; Hydroxypiracetam;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.3227 mL | 31.6136 mL | 63.2271 mL | |
| 5 mM | 1.2645 mL | 6.3227 mL | 12.6454 mL | |
| 10 mM | 0.6323 mL | 3.1614 mL | 6.3227 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT04205565 | RECRUITING | Drug:Test group:L-oxiracetam Injection Drug:Control group:Oxiracetam Injection Drug:Placebo group:Placebo Injection |
Craniocerebral Injury | Nanjing Yoko Biomedical Co.,Ltd. | 2019-09-30 | Phase 3 |
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