ANIRACETAM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H13NO3
Molecular Weight	219.2365
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)C(=O)N2CCCC2=O

InChI

InChIKey=ZXNRTKGTQJPIJK-UHFFFAOYSA-N

InChI=1S/C12H13NO3/c1-16-10-6-4-9(5-7-10)12(15)13-8-2-3-11(13)14/h4-7H,2-3,8H2,1H3

HIDE SMILES / InChI

Molecular Formula	C12H13NO3
Molecular Weight	219.2365
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8199398
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1338053 | https://www.ncbi.nlm.nih.gov/pubmed/12070527 | https://drug.mynahcare.com/drugs/genericdetail/aniracetam-MTQz

Aniracetam is a nootropic drug. It behaves as a positive modulator of AMPA-sensitive glutamate receptors. Aniracetam is clinically used in patients with mild to moderate senile dementia of the Alzheimer type. In Japan, the drug was prescribed for eight years to treat emotional disturbances, such as depressed mood and anxiety/agitation, but not memory impairment following cerebral infarction. Aniracetam (Draganon®) has been withdrawn from the Japanese market because of the unexpected failure in the latest placebo-controlled double-blind study. Animal studies demonstrated that aniracetam has clinical potential in personality disorders, anxiety, depression, posttraumatic stress disorder, attention-deficit/hyperactivity disorder, autism, negative symptoms of schizophrenia, and sleep disorders.

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/7616253 \| https://www.ncbi.nlm.nih.gov/pubmed/20163115 \| https://www.ncbi.nlm.nih.gov/pubmed/1975272 \| https://www.ncbi.nlm.nih.gov/pubmed/12869631 \| https://www.ncbi.nlm.nih.gov/pubmed/16192394 \| https://www.ncbi.nlm.nih.gov/pubmed/8824304 \| https://www.ncbi.nlm.nih.gov/pubmed/1338053 \| https://www.ncbi.nlm.nih.gov/pubmed/7476926	Positive Allosteric Modulator 186

Conditions

Condition	Modality	Targets	Highest Phase	Product
Senile dementia of the Alzheimer type 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8199398	Primary		Approved 8583	AMPAMET Approved Use Results from trials in elderly patients with mild to moderate cognitive impairment due to senile dementia of the Alzheimer type suggest that aniracetam may be of benefit, with further trials required to confirm its efficacy profile and to define more precisely those patients most likely to respond to treatment

C_max

Value	Dose	Analyte	Population
2.3 μg/L EXPERIMENT https://link.springer.com/article/10.2165/00002512-199404030-00007	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	ANIRACETAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
14.1 μg/L EXPERIMENT https://link.springer.com/article/10.2165/00002512-199404030-00007	1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered:	ANIRACETAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
8.75 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19025058/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	ANIRACETAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.332 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9062694/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	PYRROLIDONE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status:

AUC

Value	Dose	Co-administered	Analyte	Population
4.62 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19025058/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		ANIRACETAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9062694/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		PYRROLIDONE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status:

T_1/2

Value	Dose	Analyte	Population
35 min EXPERIMENT https://link.springer.com/article/10.2165/00002512-199404030-00007	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	ANIRACETAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
35 min EXPERIMENT https://link.springer.com/article/10.2165/00002512-199404030-00007	1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered:	ANIRACETAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.47 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19025058/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	ANIRACETAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
11.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9062694/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	PYRROLIDONE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status:

F_unbound

Value	Dose	Co-administered	Analyte	Population
34% EXPERIMENT https://link.springer.com/article/10.2165/00002512-199404030-00007			ANIRACETAM plasma	Homo sapiens

Doses

Dose	Population	Adverse events
1000 mg 1 times / day multiple, oral Recommended Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2188276/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2188276/	Sources: https://pubmed.ncbi.nlm.nih.gov/2188276/
750 mg 2 times / day multiple, oral Recommended Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1822317/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1822317/	Sources: https://pubmed.ncbi.nlm.nih.gov/1822317/

PubMed

Title	Date	PubMed
The cognition-enhancer nefiracetam is protective in BDNF-independent neuronal cell death under the serum-free condition.	2002 Feb	11738480
The aniracetam metabolite 2-pyrrolidinone induces a long-term enhancement in AMPA receptor responses via a CaMKII pathway.	2002 Jan 31	11834304
Effects of aniracetam on extracellular levels of transmitter amino acids in the hippocampus of the conscious gerbils: an intracranial microdialysis study.	2003 Mar 27	12633884
2-pyrrolidinone induces a long-lasting facilitation of hippocampal synaptic transmission by enhancing alpha7 ACh receptor responses via a PKC pathway.	2003 Sep 10	14499485
Mild cognitive impairment: animal models.	2004 Dec	22034045
Interactions of allosteric modulators of AMPA/kainate receptors on spreading depression in the chicken retina.	2004 Oct 29	15464752
Cognitive aging in zebrafish.	2006 Dec 20	17183640
The ampakine CX546 restores the prepulse inhibition and latent inhibition deficits in mGluR5-deficient mice.	2007 Apr	16936708
Aniracetam reversed learning and memory deficits following prenatal ethanol exposure by modulating functions of synaptic AMPA receptors.	2008 Apr	17609677
Ameliorating effects of preadolescent aniracetam treatment on prenatal ethanol-induced impairment in AMPA receptor activity.	2008 Jan	17916430

Patents

Sample Use Guides

In Vivo Use Guide

1.5 gm daily

Route of Administration: Oral

In Vitro Use Guide

Abeta25-35 (1 microM) largely increased ree calcium concentrations in frontal cortical (FC) and hippocampal (HP) synaptosomes in 3 months old mice, but this effect on HP synaptosomes was effectively reversed by aniracetam (1-4 mM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:47:15 GMT 2025` Edited by `admin` on `Mon Mar 31 17:47:15 GMT 2025`
Record UNII	5L16LKN964
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DRAGANON

Preferred Name

English

ANIRACETAM

Official Name

English

SARPUL

Brand Name

English

1-P-ANISOYL-2-PYRROLIDINONE

Common Name

English

ANIRACETAM [USAN]

Common Name

English

ANIRACETAM [MI]

Common Name

English

RO 13-5057

Code

English

ANIRACETAM [MART.]

Common Name

English

1-ANISOYL-2-PYRROLIDINONE

Systematic Name

English

1-(4-METHOXYBENZOYL)-2-PYRROLIDINONE

Systematic Name

English

NSC-758223

Code

English

RO-13-5057

Code

English

ANIRACETAM [JAN]

Common Name

English

Aniracetam [WHO-DD]

Common Name

English

aniracetam [INN]

Common Name

English

RO-135057

Code

English

Classification Tree Code System Code

WHO-VATC

QN06BX11