Aniracetam

Identification

Summary

Aniracetam is a nootropic drug used to ameliorate memory and attention disturbances accompanying cerebrovascular diseases and degenerative brain disorders.

Generic Name
Aniracetam
DrugBank Accession Number
DB04599
Background

Compound with anti-depressive properties used as a mental performance enhancer.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 219.2365
Monoisotopic: 219.089543287
Chemical Formula
C12H13NO3
Synonyms
  • 1-p-anisoylpyrrolidin-2-one
  • Aniracetam
  • Aniracetamun
External IDs
  • RO 13-5057
  • RO-13-5057

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Aniracetam possesses a wide range of anxiolytic properties, which may be mediated by an interaction between cholinergic, dopaminergic and serotonergic systems.

Mechanism of action
TargetActionsOrganism
U5-hydroxytryptamine receptor 2ANot AvailableHumans
UDopamine D2 receptorNot AvailableHumans
UGlutamate receptor 2Not AvailableHumans
UGlutamate receptor 3Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

1-2.5 hours

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Aniracetam is combined with 1,2-Benzodiazepine.
AcenocoumarolThe risk or severity of adverse effects can be increased when Aniracetam is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Aniracetam.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Aniracetam.
AclidiniumAniracetam may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Aniracetam is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Aniracetam.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Aniracetam.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Aniracetam.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Aniracetam.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Draganon / Sarpul

Categories

ATC Codes
N06BX11 — Aniracetam
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzoic acids and derivatives. These are organic compounds containing a carboxylic acid substituent attached to a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Benzoic acids and derivatives
Alternative Parents
Phenoxy compounds / Anisoles / N-acylpyrrolidines / Methoxybenzenes / Benzoyl derivatives / Alkyl aryl ethers / Pyrrolidine-2-ones / N-substituted carboxylic acid imides / Dicarboximides / Lactams
show 6 more
Substituents
2-pyrrolidone / Alkyl aryl ether / Anisole / Aromatic heteromonocyclic compound / Azacycle / Benzoic acid or derivatives / Benzoyl / Carbonyl group / Carboxylic acid derivative / Carboxylic acid imide
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
N-acylpyrrolidine, pyrrolidin-2-ones (CHEBI:47943)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
5L16LKN964
CAS number
72432-10-1
InChI Key
ZXNRTKGTQJPIJK-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-(4-methoxybenzoyl)pyrrolidin-2-one
SMILES
COC1=CC=C(C=C1)C(=O)N1CCCC1=O

References

General References
  1. Nakamura K, Kurasawa M: Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43. [Article]
  2. Lawrence JJ, Brenowitz S, Trussell LO: 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. Mol Pharmacol. 2003 Aug;64(2):269-78. [Article]
KEGG Drug
D01883
KEGG Compound
C13355
PubChem Compound
2196
PubChem Substance
46506607
ChemSpider
2111
RxNav
17939
ChEBI
47943
ChEMBL
CHEMBL36994
ZINC
ZINC000000015951
PDBe Ligand
4MP
Wikipedia
Aniracetam
PDB Entries
2al5 / 3lsw

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral750 MG
Granule, for suspensionOral
Tablet
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.47 mg/mLALOGPS
logP0.55ALOGPS
logP1.11ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.61 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.96 m3·mol-1ChemAxon
Polarizability22.6 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9953
Caco-2 permeable+0.6814
P-glycoprotein substrateNon-substrate0.6179
P-glycoprotein inhibitor INon-inhibitor0.8644
P-glycoprotein inhibitor IINon-inhibitor0.9519
Renal organic cation transporterNon-inhibitor0.508
CYP450 2C9 substrateNon-substrate0.8037
CYP450 2D6 substrateNon-substrate0.7021
CYP450 3A4 substrateSubstrate0.6308
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorInhibitor0.8026
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8852
CYP450 3A4 inhibitorNon-inhibitor0.9599
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7942
Ames testNon AMES toxic0.7612
CarcinogenicityNon-carcinogens0.9321
BiodegradationReady biodegradable0.7809
Rat acute toxicity1.7192 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.873
hERG inhibition (predictor II)Non-inhibitor0.8908
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-2900000000-45360e23a7cf883fc4ca
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-3910100000-60c0c22d8fe8fadda402

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Nakamura K, Kurasawa M: Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Nakamura K, Kurasawa M: Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ionotropic glutamate receptor activity
Specific Function
Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory ne...
Gene Name
GRIA2
Uniprot ID
P42262
Uniprot Name
Glutamate receptor 2
Molecular Weight
98820.32 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Extracellular-glutamate-gated ion channel activity
Specific Function
Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory ne...
Gene Name
GRIA3
Uniprot ID
P42263
Uniprot Name
Glutamate receptor 3
Molecular Weight
101155.975 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created on September 11, 2007 17:48 / Updated on June 12, 2021 10:53