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
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
| 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 |
DescriptionCurator'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
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 Aniracetam (Draganon®) has been withdrawn from the Japanese market because of the unexpected failure in the latest placebo-controlled double-blind study.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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | AMPAMET Approved UseResults 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 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.3 μg/L |
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 |
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: |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
35 min |
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 |
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: |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
34% |
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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
|
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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| How right is the righting reflex? The risk of false positives in neuroprotection studies using behavioral measures to certify forebrain ischemia. | 2010-11 |
|
| Herbal therapy: a new pathway for the treatment of Alzheimer's disease. | 2010-10-22 |
|
| Activation of AMPA receptors in the suprachiasmatic nucleus phase-shifts the mouse circadian clock in vivo and in vitro. | 2010-06-03 |
|
| Retinohypothalamic tract synapses in the rat suprachiasmatic nucleus demonstrate short-term synaptic plasticity. | 2010-05 |
|
| Piracetam defines a new binding site for allosteric modulators of alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) receptors. | 2010-03-11 |
|
| Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders. | 2010-02-12 |
|
| [Influence of aniracetam on the learning ability, memory ability and the expression of BCL-2 of hippocampal in vascular dementia model rats]. | 2009-05 |
|
| Aniracetam and DNQX affect the acquisition of rapid tolerance to ethanol in mice. | 2009-03 |
|
| Content determination of aniracetam in aniracetam inclusion complex by HPLC. | 2009 |
|
| Relative roles of different mechanisms of depression at the mouse endbulb of Held. | 2008-05 |
|
| Aniracetam reversed learning and memory deficits following prenatal ethanol exposure by modulating functions of synaptic AMPA receptors. | 2008-04 |
|
| [Effects of Goutengsan on model of Alzheimer dementia in rats by AlCl3]. | 2008-03 |
|
| Participation of hippocampal ionotropic glutamate receptors in histamine H(1) antagonist-induced memory deficit in rats. | 2008-03 |
|
| [A randomized, controlled, double-blind trial of Huannao Yicong capsule in senile patients with mild cognitive impairment]. | 2008-01 |
|
| Ameliorating effects of preadolescent aniracetam treatment on prenatal ethanol-induced impairment in AMPA receptor activity. | 2008-01 |
|
| Pharmacokinetics and bioequivalence study of aniracetam after single-dose administration in healthy Chinese male volunteers. | 2008 |
|
| Sensitive and selective liquid chromatography-tandem mass spectrometry method for the quantification of aniracetam in human plasma. | 2007-10-15 |
|
| [Clinical study on a randomized, double-blind control of Shenwu gelatin capsule in treatment of mild cognitive impairment]. | 2007-09 |
|
| Identification of a putative binding site for 5-alkyl-benzothiadiazides in the AMPA receptor dimer interface. | 2007-07 |
|
| Postnatal aniracetam treatment improves prenatal ethanol induced attenuation of AMPA receptor-mediated synaptic transmission. | 2007-06 |
|
| AMPA receptor potentiators: application for depression and Parkinson's disease. | 2007-05 |
|
| Pharmacology of ampakine modulators: from AMPA receptors to synapses and behavior. | 2007-05 |
|
| The ampakine CX546 restores the prepulse inhibition and latent inhibition deficits in mGluR5-deficient mice. | 2007-04 |
|
| Progress update: Pharmacological treatment of Alzheimer's disease. | 2007 |
|
| Aniracetam restores the effects of amyloid-beta protein or ageing on membrane fluidity and intracellular calcium concentration in mice synaptosomes. | 2007 |
|
| Cognitive aging in zebrafish. | 2006-12-20 |
|
| Enantiomeric impurity determination of levetiracetam using capillary electrochromatography. | 2006-12 |
|
| In search of novel AMPA potentiators. | 2006-11 |
|
| Aniracetam attenuates H2O2-induced deficiency of neuron viability, mitochondria potential and hippocampal long-term potentiation of mice in vitro. | 2006-09 |
|
| Delayed, post-injury treatment with aniracetam improves cognitive performance after traumatic brain injury in rats. | 2006-08 |
|
| Brahmi rasayana improves learning and memory in mice. | 2006-03 |
|
| The alkaloid alstonine: a review of its pharmacological properties. | 2006-03 |
|
| Regulation of glutamatergic signalling by PACAP in the mammalian suprachiasmatic nucleus. | 2006-02-16 |
|
| Nardostachys jatamansi improves learning and memory in mice. | 2006 |
|
| Mechanism of positive allosteric modulators acting on AMPA receptors. | 2005-09-28 |
|
| Nootropic agents enhance the recruitment of fast GABAA inhibition in rat neocortex. | 2005-07 |
|
| Effects of propofol on recombinant AMPA receptor channels. | 2005-03-21 |
|
| Mild cognitive impairment: animal models. | 2004-12 |
|
| Interactions of allosteric modulators of AMPA/kainate receptors on spreading depression in the chicken retina. | 2004-10-29 |
|
| Effect of aniracetam on phosphatidylinositol transfer protein alpha in cytosolic and plasma membrane fractions of astrocytes subjected to simulated ischemia in vitro. | 2004-10-08 |
|
| Nootropic nefiracetam inhibits proconvulsant action of peripheral-type benzodiazepines in epileptic mutant EL mice. | 2004-10 |
|
| AMPA protects cultured neurons against glutamate excitotoxicity through a phosphatidylinositol 3-kinase-dependent activation in extracellular signal-regulated kinase to upregulate BDNF gene expression. | 2004-08 |
|
| Erk1/2 and Akt kinases are involved in the protective effect of aniracetam in astrocytes subjected to simulated ischemia in vitro. | 2004-06-28 |
|
| Human models as tools in the development of psychotropic drugs. | 2002-12 |
|
| Hydrolytic profile for ester- or amide-linkage by carboxylesterases pI 5.3 and 4.5 from human liver. | 1997-08 |
|
| Allosteric potentiation of quisqualate receptors by a nootropic drug aniracetam. | 1990-05 |
|
| Effects of N-(2,6-dimethylphenyl)-2-(2-oxo-1-pyrrolidinyl)acetamide (DM-9384) on learning and memory in rats. | 1989-05 |
|
| Effects of aniracetam on one-trial passive avoidance tests and cholinergic neurons in discrete brain regions of rats. | 1989-03-01 |
|
| Interactions between oxiracetam, aniracetam and scopolamine on behavior and brain acetylcholine. | 1987-07 |
|
| Effects of the novel compound aniracetam (Ro 13-5057) upon impaired learning and memory in rodents. | 1982 |
Patents
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:47:15 GMT 2025
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| Record UNII |
5L16LKN964
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| Record Status |
Validated (UNII)
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WHO-VATC |
QN06BX11
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DSLD |
1888 (Number of products:3)
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WHO-ATC |
N06BX11
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NCI_THESAURUS |
C1509
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100000086927
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47943
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SUB05517MIG
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4902
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m1925
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CHEMBL36994
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ANIRACETAM
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758223
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C036466
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17939
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DB04599
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DTXSID5045128
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72432-10-1
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C65236
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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Low-impact AMPAR PAMs decrease AMPAR deactivation (channel closing) alone to augment synaptic currents
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ACTIVE MOIETY |
