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
Structure for Aniracetam (DB04599)
- 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
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Target Actions Organism UGlutamate receptor 2 Not Available Humans UGlutamate receptor 3 Not Available Humans U5-hydroxytryptamine receptor 2A Not Available Humans UDopamine D2 receptor Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Aniracetam is combined with 1,2-Benzodiazepine. Acenocoumarol The risk or severity of adverse effects can be increased when Aniracetam is combined with Acenocoumarol. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Aniracetam. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Aniracetam. Agomelatine The risk or severity of adverse effects can be increased when Aniracetam is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Aniracetam. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Aniracetam. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Aniracetam. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Aniracetam. Alprazolam The risk or severity of adverse effects can be increased when Alprazolam is combined with Aniracetam. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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
- 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]
- 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]
- External Links
- KEGG Drug
- D01883
- KEGG Compound
- C13355
- PubChem Compound
- 2196
- PubChem Substance
- 46506607
- ChemSpider
- 2111
- 17939
- ChEBI
- 47943
- ChEMBL
- CHEMBL36994
- ZINC
- ZINC000000015951
- PDBe Ligand
- 4MP
- Wikipedia
- Aniracetam
- PDB Entries
- 2al5 / 3lsw
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral 750 MG Granule, for suspension Oral Tablet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.47 mg/mL ALOGPS logP 0.55 ALOGPS logP 1.11 Chemaxon logS -2 ALOGPS pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 46.61 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 58.96 m3·mol-1 Chemaxon Polarizability 22.6 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9953 Caco-2 permeable + 0.6814 P-glycoprotein substrate Non-substrate 0.6179 P-glycoprotein inhibitor I Non-inhibitor 0.8644 P-glycoprotein inhibitor II Non-inhibitor 0.9519 Renal organic cation transporter Non-inhibitor 0.508 CYP450 2C9 substrate Non-substrate 0.8037 CYP450 2D6 substrate Non-substrate 0.7021 CYP450 3A4 substrate Substrate 0.6308 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Inhibitor 0.8026 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Inhibitor 0.8852 CYP450 3A4 inhibitor Non-inhibitor 0.9599 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7942 Ames test Non AMES toxic 0.7612 Carcinogenicity Non-carcinogens 0.9321 Biodegradation Ready biodegradable 0.7809 Rat acute toxicity 1.7192 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.873 hERG inhibition (predictor II) Non-inhibitor 0.8908
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-000i-2900000000-45360e23a7cf883fc4ca MS/MS Spectrum - , positive LC-MS/MS splash10-000i-3910100000-60c0c22d8fe8fadda402
Targets
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- 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
- 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
- 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
- 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
- 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
- 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]
Drug created at September 11, 2007 17:48 / Updated at June 12, 2021 10:53