OXIRACETAM

Details

Stereochemistry	UNKNOWN
Molecular Formula	C6H10N2O3
Molecular Weight	158.1552
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)CN1CC(O)CC1=O

InChI

InChIKey=IHLAQQPQKRMGSS-UHFFFAOYSA-N

InChI=1S/C6H10N2O3/c7-5(10)3-8-2-4(9)1-6(8)11/h4,9H,1-3H2,(H2,7,10)

HIDE SMILES / InChI

Molecular Formula	C6H10N2O3
Molecular Weight	158.1552
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9369316
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1444879 | https://www.ncbi.nlm.nih.gov/pubmed/7586900 | https://www.ncbi.nlm.nih.gov/pubmed/8456595 | https://www.ncbi.nlm.nih.gov/pubmed/3556550

Oxiracetam (ISF 2522) is a water-soluble ampakine of the nootropic racetam chemical class. Oxiracetam is a positive AMPA modulator similar in mechanism and potency (but not the binding site) to both piracetam and aniracetam but may have an additional benefit of increasing glutamate, acetylcholine, and D-aspartic acid release from activated but not resting neurons. Oxiracetam has been proved as an efficient memory enhancer if taken consistently. Additionally, studies have revealed positive impacts on demented patients in the long term. Thus, the drug enhances an overall quality of life of patients suffering from ADHD, dementia, and other neurological problems. Oxiracetam is one of the most popular nootropics, well known and highly regarded for its outstanding cognitive enhancement properties and mild stimulant capability. It has also been proven to be safe and well tolerated even at high dosages, and its moderate cost, ready availability and “stackability” make it a must-have for many nootropic users.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate receptor ionotropic AMPA 41 Target ID: CHEMBL2096670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1338053	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1444879	Primary		Not Provided 504	Neuromed Approved Use Unknown
Degenerative dementia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8456595	Primary		Approved 8429	Neuromed Approved Use Unknown

PubMed

Title	Date	PubMed
Interactions between oxiracetam, aniracetam and scopolamine on behavior and brain acetylcholine.	1987 Jul	3659072
Brain entry and direct central pharmacological effects of the nootropic drug oxiracetam. Oxiracetam: brain entry and pharmacological effects.	1989 Oct	2602442
Effect of oxiracetam on scopolamine-induced amnesia in the rat in a spatial learning task.	1992 Nov	1448491
Synthesis and pharmacological activity of a series of dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones, a novel class of potent cognition enhancers.	1993 Dec 24	8277504
The effects of ascorbic acid and oxiracetam on scopolamine-induced amnesia in a habituation test in aged mice.	1995 Sep	7582819
Aniracetam improves contextual fear conditioning and increases hippocampal gamma-PKC activation in DBA/2J mice.	2002	11918291
Human models as tools in the development of psychotropic drugs.	2002 Dec	22034241
Oxiracetam prevented the scopolamine but not the diazepam induced memory deficits in mice.	2002 Jul 18	12110475
Mild cognitive impairment: animal models.	2004 Dec	22034045
Rapid quantitative analysis of oxiracetam in human plasma by liquid chromatography/electrospray tandem mass spectrometry.	2004 Nov 15	15522546
Nootropic nefiracetam inhibits proconvulsant action of peripheral-type benzodiazepines in epileptic mutant EL mice.	2004 Oct	15542710
Rapid quantitative analysis of oxiracetam in human plasma by liquid chromatography/electrospray tandem mass spectrometry.	2004 Sep 21	15351064
Oxiracetam pre- but not post-treatment prevented social recognition deficits produced with trimethyltin in rats.	2005 Jun 20	15922047
[Evaluation of antihypoxic and antiamnemonic effects of mexicor in animals].	2009 Nov-Dec	20169737
[Optimization of preparation of poly ( glycidyl methacrylate-divinylbenzene) monolithic column with orthogonal experiments for separation of small molecules].	2010 Feb	20556957
Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders.	2010 Feb 12	20166767
Efficacy study of Prunus amygdalus (almond) nuts in scopolamine-induced amnesia in rats.	2010 Jun	20871769
Determination of piracetam in rat plasma by LC-MS/MS and its application to pharmacokinetics.	2010 Oct	20352612

Patents

Sample Use Guides

In Vivo Use Guide

800 mg bid (1600 mg/day)

Route of Administration: Oral

In Vitro Use Guide

To record currents through Ca2+ channels, a whole cell variation of the patch-clamp technique was applied to NG108-15 cells. Step depolarizations lasting 160 milliseconds were applied to a holding potential of −50 mV to induce high-voltage– activated (HVA) Ca2+ channel currents. Under such experimental conditions, low-voltage–activated (LVA) Ttype Ca2+ channels were practically inactivated at the end of the pulse, allowing us to measure the amplitude of N/L-type Ca2+ channel currents. The external and internal (pipette-filling) solutions were designed to separate Ca2+ channel currents from other ionic currents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:07:11 GMT 2023` Edited by `admin` on `Fri Dec 15 15:07:11 GMT 2023`
Record UNII	P7U817352G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXIRACETAM

Official Name

English

OXIRACETAM [JAN]

Common Name

English

CGP-21690E

Code

English

GNF-PF-1005

Code

English

CGP 21690E

Code

English

Oxiracetam [WHO-DD]

Common Name

English

oxiracetam [INN]

Common Name

English

OXIRACETAM [MI]

Common Name

English

OXIRACETAM [MART.]

Common Name

English

4-HYDROXY-2-OXO-PYRROLIDINACETAMIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1509