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 42 Target ID: CHEMBL2096670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1338053	Positive Allosteric Modulator 186

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1444879	Primary		Not Provided 511	Neuromed Approved Use Unknown
Degenerative dementia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8456595	Primary		Approved 8583	Neuromed Approved Use Unknown

C_max

Value	Dose	Analyte	Population
196 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2253653/	800 mg 2 times / day multiple, oral dose: 800 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OXIRACETAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
140 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2253653/	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	OXIRACETAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
107 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2253653/	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	OXIRACETAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
1360 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2253653/	800 mg 2 times / day multiple, oral dose: 800 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OXIRACETAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1383 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2253653/	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	OXIRACETAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
511 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2253653/	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	OXIRACETAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
16.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2253653/	800 mg 2 times / day multiple, oral dose: 800 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OXIRACETAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
12.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2253653/	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	OXIRACETAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
7.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2253653/	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	OXIRACETAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
800 mg 2 times / day multiple, oral Recommended Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1603291/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1603291/	Sources: https://pubmed.ncbi.nlm.nih.gov/1603291/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429	P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/4626#section=Biological-Test-Results Page: 83.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/4626#section=Biological-Test-Results Page: 90 \| 91	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/4626#section=Biological-Test-Results Page: 52.0

PubMed

Title	Date	PubMed
Determination of piracetam in rat plasma by LC-MS/MS and its application to pharmacokinetics.	2010-10	20352612
Efficacy study of Prunus amygdalus (almond) nuts in scopolamine-induced amnesia in rats.	2010-06	20871769
[Evaluation of antihypoxic and antiamnemonic effects of mexicor in animals].	2010-02-23	20169737
Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders.	2010-02-12	20166767
[Optimization of preparation of poly ( glycidyl methacrylate-divinylbenzene) monolithic column with orthogonal experiments for separation of small molecules].	2010-02	20556957
Oxiracetam pre- but not post-treatment prevented social recognition deficits produced with trimethyltin in rats.	2005-06-20	15922047
Mild cognitive impairment: animal models.	2004-12	22034045
Rapid quantitative analysis of oxiracetam in human plasma by liquid chromatography/electrospray tandem mass spectrometry.	2004-11-15	15522546
Nootropic nefiracetam inhibits proconvulsant action of peripheral-type benzodiazepines in epileptic mutant EL mice.	2004-10	15542710
Rapid quantitative analysis of oxiracetam in human plasma by liquid chromatography/electrospray tandem mass spectrometry.	2004-09-21	15351064
Human models as tools in the development of psychotropic drugs.	2002-12	22034241
Oxiracetam prevented the scopolamine but not the diazepam induced memory deficits in mice.	2002-07-18	12110475
Aniracetam improves contextual fear conditioning and increases hippocampal gamma-PKC activation in DBA/2J mice.	2002	11918291
The effects of ascorbic acid and oxiracetam on scopolamine-induced amnesia in a habituation test in aged mice.	1995-09	7582819
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.	1993-12-24	8277504
Effect of oxiracetam on scopolamine-induced amnesia in the rat in a spatial learning task.	1992-11	1448491
Brain entry and direct central pharmacological effects of the nootropic drug oxiracetam. Oxiracetam: brain entry and pharmacological effects.	1989-10	2602442
Interactions between oxiracetam, aniracetam and scopolamine on behavior and brain acetylcholine.	1987-07	3659072

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 `Mon Mar 31 17:47:05 GMT 2025` Edited by `admin` on `Mon Mar 31 17:47:05 GMT 2025`
Record UNII	P7U817352G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CGP-21690E

Preferred Name

English

OXIRACETAM

Official Name

English

OXIRACETAM [JAN]

Common Name

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