(S)-Oxiracetam | CAS#88929-35-5 | AMPA receptor modulator

(S)-Oxiracetam
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561589

CAS#: 88929-35-5

Description: (S)-Oxiracetam is a positive allosteric modulator of the AMPA receptors.

Chemical Structure

(S)-Oxiracetam

CAS# 88929-35-5

Instruction

Theoretical Analysis

MedKoo Cat#: 561589
Name: (S)-Oxiracetam
CAS#: 88929-35-5
Chemical Formula: C6H10N2O3
Exact Mass: 158.07
Molecular Weight: 158.150
Elemental Analysis: C, 45.57; H, 6.37; N, 17.71; O, 30.35

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 450
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: (S)-Oxiracetam; S-Oxiracetam; (S)-ISF-2522;

IUPAC/Chemical Name: 2-[(4S)-4-hydroxy-2-oxopyrrolidin-1-yl]acetamide

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

SMILES Code: O=C(N)CN1C(C[C@H](O)C1)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 158.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Li W, Liu H, Jiang H, Wang C, Guo Y, Sun Y, Zhao X, Xiong X, Zhang X, Zhang K, Nie Z, Pu X. (S)-Oxiracetam is the Active Ingredient in Oxiracetam that Alleviates the Cognitive Impairment Induced by Chronic Cerebral Hypoperfusion in Rats. Sci Rep. 2017 Aug 30;7(1):10052. doi: 10.1038/s41598-017-10283-4. PubMed PMID: 28855592; PubMed Central PMCID: PMC5577264.

2: Huang L, Shang E, Fan W, Li X, Li B, He S, Fu Y, Zhang Y, Li Y, Fang W. S-oxiracetam protect against ischemic stroke via alleviating blood brain barrier dysfunction in rats. Eur J Pharm Sci. 2017 Nov 15;109:40-47. doi: 10.1016/j.ejps.2017.07.029. Epub 2017 Jul 29. PubMed PMID: 28760594.

3: Wang W, Ji H, Li T, Jia Y, Xie H. Pharmacokinetic comparisons of S-oxiracetam and R-oxiracetam in beagle dogs. Acta Pharm. 2016 Jun 1;66(2):279-87. doi: 10.1515/acph-2016-0013. PubMed PMID: 27279070.

4: Zhang Q, Yang W, Zhang Q, Yang Y, Li J, Lu Y, Zheng Y, He J, Zhao D, Chen X. Enantioselective HPLC determination of oxiracetam enantiomers and application to a pharmacokinetic study in beagle dogs. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jul 1;993-994:9-13. doi: 10.1016/j.jchromb.2015.04.033. Epub 2015 Apr 30. PubMed PMID: 25978861.

5: Chen J, Zhou SN, Zhang YM, Feng YL, Wang S. Glycosides of cistanche improve learning and memory in the rat model of vascular dementia. Eur Rev Med Pharmacol Sci. 2015 Apr;19(7):1234-40. PubMed PMID: 25912583.

6: Zhang Q, Yang W, Yang Y, Xing H, Zhang Q, Li J, Lu Y, He J, Yang S, Zhao D, Chen X. Comparative pharmacokinetic studies of racemic oxiracetam and its pure enantiomers after oral administration in rats by a stereoselective HPLC method. J Pharm Biomed Anal. 2015;111:153-8. doi: 10.1016/j.jpba.2015.03.039. Epub 2015 Apr 4. PubMed PMID: 25886392.

7: Wang C, Li F, Guan Y, Zhu L, Fei Y, Zhang J, Pan Y. Bone marrow stromal cells combined with oxiracetam influences the expression of B-cell lymphoma 2 in rats with ischemic stroke. J Stroke Cerebrovasc Dis. 2014 Nov-Dec;23(10):2591-7. doi: 10.1016/j.jstrokecerebrovasdis.2014.05.035. Epub 2014 Sep 26. PubMed PMID: 25267587.

8: Wan X, Wang H, Ma P, Xi L, Sun J, He Z, Zhang X, Liu X. Simultaneous determination of oxiracetam and its degraded substance in rat plasma by HPLC-MS/MS and its application to pharmacokinetic study after a single high-dose intravenous administration. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Oct 15;969:95-100. doi: 10.1016/j.jchromb.2014.07.041. Epub 2014 Aug 4. PubMed PMID: 25168792.

9: Lee DS, Ryu HJ, Kim JE, Choi HC, Kim YI, Song HK, Kang TC. The effect of levetiracetam on status epilepticus-induced neuronal death in the rat hippocampus. Seizure. 2013 Jun;22(5):368-77. doi: 10.1016/j.seizure.2013.02.005. Epub 2013 Mar 13. PubMed PMID: 23490457.

10: Hlinák Z, Krejcí I. Oxiracetam pre- but not post-treatment prevented social recognition deficits produced with trimethyltin in rats. Behav Brain Res. 2005 Jun 20;161(2):213-9. Epub 2005 Mar 31. PubMed PMID: 15922047.

11: Son J, Lee J, Lee M, Lee E, Lee JH, La S, Kim DH. Rapid quantitative analysis of oxiracetam in human plasma by liquid chromatography/electrospray tandem mass spectrometry. J Pharm Biomed Anal. 2004 Nov 15;36(3):657-61. PubMed PMID: 15522546.

12: Son J, Lee J, Lee M, Lee E, Lee KT, La S, Kim DH. Rapid quantitative analysis of oxiracetam in human plasma by liquid chromatography/electrospray tandem mass spectrometry. J Pharm Biomed Anal. 2004 Sep 21;36(1):183-7. PubMed PMID: 15351064.

13: Hlinák Z, Krejcí I. Oxiracetam prevented the scopolamine but not the diazepam induced memory deficits in mice. Behav Brain Res. 2002 Jul 18;133(2):395-9. PubMed PMID: 12110475.

14: Smith AM, Wehner JM. Aniracetam improves contextual fear conditioning and increases hippocampal gamma-PKC activation in DBA/2J mice. Hippocampus. 2002;12(1):76-85. PubMed PMID: 11918291.

15: Hlinák Z, Krejcí I. Oxiracetam prevents the MK-801 induced amnesia for the elevated plus-maze in mice. Behav Brain Res. 2000 Dec 20;117(1-2):147-51. PubMed PMID: 11099768.

16: Gabryel B, Trzeciak HI, Pudełko A, Cieślik P. Influence of piracetam and oxiracetam on the content of high-energy phosphates and morphometry of astrocytes in vitro. Pol J Pharmacol. 1999 Nov-Dec;51(6):485-95. PubMed PMID: 10817526.

17: Pittaluga A, Pattarini R, Andrioli GC, Viola C, Munari C, Raiteri M. Activity of putative cognition enhancers in kynurenate test performed with human neocortex slices. J Pharmacol Exp Ther. 1999 Jul;290(1):423-8. PubMed PMID: 10381808.

18: Itil TM, Eralp E, Ahmed I, Kunitz A, Itil KZ. The pharmacological effects of ginkgo biloba, a plant extract, on the brain of dementia patients in comparison with tacrine. Psychopharmacol Bull. 1998;34(3):391-7. PubMed PMID: 9803773.

19: Lu Y, Wehner JM. Enhancement of contextual fear-conditioning by putative (+/-)-alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA) receptor modulators and N-methyl-D-aspartate (NMDA) receptor antagonists in DBA/2J mice. Brain Res. 1997 Sep 12;768(1-2):197-207. PubMed PMID: 9369316.

20: Pittaluga A, Vaccari D, Raiteri M. The "kynurenate test", a biochemical assay for putative cognition enhancers. J Pharmacol Exp Ther. 1997 Oct;283(1):82-90. PubMed PMID: 9336311.

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