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 Aniracetam (Draganon®) has been withdrawn from the Japanese market because of the unexpected failure in the latest placebo-controlled double-blind study.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 41 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 179

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 8429	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

PubMed

Title	Date	PubMed
Effects of the novel compound aniracetam (Ro 13-5057) upon impaired learning and memory in rodents.	1982	6817363
Interactions between oxiracetam, aniracetam and scopolamine on behavior and brain acetylcholine.	1987 Jul	3659072
Effects of aniracetam on one-trial passive avoidance tests and cholinergic neurons in discrete brain regions of rats.	1989 Mar-Apr	2757465
Effects of N-(2,6-dimethylphenyl)-2-(2-oxo-1-pyrrolidinyl)acetamide (DM-9384) on learning and memory in rats.	1989 May	2724699
Allosteric potentiation of quisqualate receptors by a nootropic drug aniracetam.	1990 May	1975272
Hydrolytic profile for ester- or amide-linkage by carboxylesterases pI 5.3 and 4.5 from human liver.	1997 Aug	9300133
Sialic acid 9-O-acetylesterase catalyzes the hydrolyzing reaction from alacepril to deacetylalacepril.	2003 Aug	12948030
The mechanism of action of aniracetam at synaptic alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors: indirect and direct effects on desensitization.	2003 Aug	12869631
Multiple sclerosis and glutamate.	2003 May	12853317
Facilitation of alpha-amino-3-hydroxy-5-methylisoxazole-4-propionate receptor transmission in the suprachiasmatic nucleus by aniracetam enhances photic responses of the biological clock in rodents.	2003 May	12716429
Multiple molecular determinants for allosteric modulation of alternatively spliced AMPA receptors.	2003 Nov 26	14645491
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
The cognition-enhancer nefiracetam inhibits both necrosis and apoptosis in retinal ischemic models in vitro and in vivo.	2004 Apr	14718588
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 Aug	15287886
Mild cognitive impairment: animal models.	2004 Dec	22034045
AMPA receptor potentiators for the treatment of CNS disorders.	2004 Jun	15180479
Piracetam and TRH analogues antagonise inhibition by barbiturates, diazepam, melatonin and galanin of human erythrocyte D-glucose transport.	2004 Jun	15148255
Erk1/2 and Akt kinases are involved in the protective effect of aniracetam in astrocytes subjected to simulated ischemia in vitro.	2004 Jun 28	15212964
Nootropic nefiracetam inhibits proconvulsant action of peripheral-type benzodiazepines in epileptic mutant EL mice.	2004 Oct	15542710
Nootropic agents enhance the recruitment of fast GABAA inhibition in rat neocortex.	2005 Jul	15459084
Effects of propofol on recombinant AMPA receptor channels.	2005 Mar 21	15777773
Mechanism of positive allosteric modulators acting on AMPA receptors.	2005 Sep 28	16192394
Effect of aniracetam on phosphatidylinositol transfer protein alpha in cytosolic and plasma membrane fractions of astrocytes subjected to simulated ischemia in vitro.	2005 Sep-Oct	16227651
Delayed, post-injury treatment with aniracetam improves cognitive performance after traumatic brain injury in rats.	2006 Aug	16928181
Enantiomeric impurity determination of levetiracetam using capillary electrochromatography.	2006 Dec	17305245
Regulation of glutamatergic signalling by PACAP in the mammalian suprachiasmatic nucleus.	2006 Feb 16	16483357
Brahmi rasayana improves learning and memory in mice.	2006 Mar	16550227
Aniracetam attenuates H2O2-induced deficiency of neuron viability, mitochondria potential and hippocampal long-term potentiation of mice in vitro.	2006 Sep	17690727
Nardostachys jatamansi improves learning and memory in mice.	2006 Spring	16579738
Progress update: Pharmacological treatment of Alzheimer's disease.	2007	19300586
Aniracetam restores the effects of amyloid-beta protein or ageing on membrane fluidity and intracellular calcium concentration in mice synaptosomes.	2007	17557127
The ampakine CX546 restores the prepulse inhibition and latent inhibition deficits in mGluR5-deficient mice.	2007 Apr	16936708
Identification of a putative binding site for 5-alkyl-benzothiadiazides in the AMPA receptor dimer interface.	2007 Jul	16916614
Postnatal aniracetam treatment improves prenatal ethanol induced attenuation of AMPA receptor-mediated synaptic transmission.	2007 Jun	17493826
AMPA receptor potentiators: application for depression and Parkinson's disease.	2007 May	17504104
Pharmacology of ampakine modulators: from AMPA receptors to synapses and behavior.	2007 May	17504103
[Clinical study on a randomized, double-blind control of Shenwu gelatin capsule in treatment of mild cognitive impairment].	2007 Sep	17993008
Pharmacokinetics and bioequivalence study of aniracetam after single-dose administration in healthy Chinese male volunteers.	2008	19025058
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
[Effects of Goutengsan on model of Alzheimer dementia in rats by AlCl3].	2008 Mar	18536382
Relative roles of different mechanisms of depression at the mouse endbulb of Held.	2008 May	18367696
Content determination of aniracetam in aniracetam inclusion complex by HPLC.	2009	19412824
[Influence of aniracetam on the learning ability, memory ability and the expression of BCL-2 of hippocampal in vascular dementia model rats].	2009 May	21189545
Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders.	2010 Feb 12	20166767
Activation of AMPA receptors in the suprachiasmatic nucleus phase-shifts the mouse circadian clock in vivo and in vitro.	2010 Jun 3	20532181
Piracetam defines a new binding site for allosteric modulators of alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) receptors.	2010 Mar 11	20163115
Retinohypothalamic tract synapses in the rat suprachiasmatic nucleus demonstrate short-term synaptic plasticity.	2010 May	20220078
How right is the righting reflex? The risk of false positives in neuroprotection studies using behavioral measures to certify forebrain ischemia.	2010 Nov	20444328
Herbal therapy: a new pathway for the treatment of Alzheimer's disease.	2010 Oct 22	21067555

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 `Fri Dec 15 15:07:25 GMT 2023` Edited by `admin` on `Fri Dec 15 15:07:25 GMT 2023`
Record UNII	5L16LKN964
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANIRACETAM

Official Name

English

SARPUL

Brand Name

English

1-P-ANISOYL-2-PYRROLIDINONE

Common Name

English

DRAGANON

Brand 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