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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 of ANIRACETAM

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

Description

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 Aniracetam (Draganon®) has been withdrawn from the Japanese market because of the unexpected failure in the latest placebo-controlled double-blind study.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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMPAMET

Cmax

ValueDoseCo-administeredAnalytePopulation
2.3 μg/L
300 mg single, oral
ANIRACETAM plasma
Homo sapiens
14.1 μg/L
1200 mg single, oral
ANIRACETAM plasma
Homo sapiens
8.75 ng/mL
400 mg single, oral
ANIRACETAM plasma
Homo sapiens
0.332 μg/mL
200 mg single, oral
PYRROLIDONE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
4.62 ng × h/mL
400 mg single, oral
ANIRACETAM plasma
Homo sapiens
2.5 μg × h/mL
200 mg single, oral
PYRROLIDONE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
35 min
300 mg single, oral
ANIRACETAM plasma
Homo sapiens
35 min
1200 mg single, oral
ANIRACETAM plasma
Homo sapiens
0.47 h
400 mg single, oral
ANIRACETAM plasma
Homo sapiens
11.5 h
200 mg single, oral
PYRROLIDONE serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
34%
ANIRACETAM plasma
Homo sapiens

Doses

PubMed

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).