Aniracetam
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Explore a selection of our essential drug information below, or:
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
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Disturbance in attention •••••••••••• ••••••• •••••••• ••• ••••••••••• ••••••• •••• •••••• Management of Disturbance in attention •••••••••••• ••••••• •••••••• ••• ••••••••••• ••••••• •••• •••••• Management of Memory disturbances •••••••••••• ••••••• •••••••• ••• ••••••••••• ••••••• •••• •••••• Management of Memory disturbances •••••••••••• ••••••• •••••••• ••• ••••••••••• ••••••• •••• •••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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 AD(2) dopamine receptor inhibitorHumans A5-hydroxytryptamine receptor 2A inhibitorHumans UGlutamate receptor 2 Not Available Humans UGlutamate receptor 3 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. View sample adverse effects data in our new Data Library!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 CNS depression 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 CNS depression can be increased when Acetazolamide is combined with Aniracetam. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Aniracetam. Agomelatine The risk or severity of CNS depression can be increased when Aniracetam is combined with Agomelatine. - 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
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Granule, for suspension Oral 1500 MG 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 158.9389069 predictedDarkChem Lite v0.1.0 [M-H]- 147.36322 predictedDeepCCS 1.0 (2019) [M+H]+ 159.9679069 predictedDarkChem Lite v0.1.0 [M+H]+ 149.72122 predictedDeepCCS 1.0 (2019) [M+Na]+ 159.4877069 predictedDarkChem Lite v0.1.0 [M+Na]+ 156.45332 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
1. DetailsD(2) dopamine receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase (PubMed:21645528). Positively regulates postnatal regression of retinal hyaloid vessels via suppression of VEGFR2/KDR activity, downstream of OPN5 (By similarity)
- Specific Function
- dopamine binding
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. Details5-hydroxytryptamine receptor 2A
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:1330647, PubMed:18703043, PubMed:19057895, PubMed:21645528, PubMed:22300836, PubMed:35084960, PubMed:38552625). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD) (PubMed:28129538, PubMed:35084960). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:28129538, PubMed:35084960). HTR2A is coupled to G(q)/G(11) G alpha proteins and activates phospholipase C-beta, releasing diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) second messengers that modulate the activity of phosphatidylinositol 3-kinase and promote the release of Ca(2+) ions from intracellular stores, respectively (PubMed:18703043, PubMed:28129538, PubMed:35084960). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:28129538, PubMed:35084960). Affects neural activity, perception, cognition and mood (PubMed:18297054). Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction (By similarity)
- Specific Function
- 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
3. DetailsGlutamate receptor 2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ionotropic glutamate receptor that functions as a ligand-gated cation channel, gated by L-glutamate and glutamatergic agonists such as alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA), quisqualic acid, and kainic acid (PubMed:20614889, PubMed:31300657, PubMed:8003671). L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system and plays an important role in fast excitatory synaptic transmission (PubMed:14687553). Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse upon entry of monovalent and divalent cations such as sodium and calcium (PubMed:20614889, PubMed:8003671). The receptor then desensitizes rapidly and enters in a transient inactive state, characterized by the presence of bound agonist (By similarity). In the presence of CACNG4 or CACNG7 or CACNG8, shows resensitization which is characterized by a delayed accumulation of current flux upon continued application of L-glutamate (By similarity). Through complex formation with NSG1, GRIP1 and STX12 controls the intracellular fate of AMPAR and the endosomal sorting of the GRIA2 subunit toward recycling and membrane targeting (By similarity)
- Specific Function
- AMPA glutamate receptor activity
- 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]
4. DetailsGlutamate receptor 3
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ionotropic glutamate receptor that functions as a ligand-gated cation channel, gated by L-glutamate and glutamatergic agonists such as alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA), quisqualic acid, and kainic acid (By similarity). L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system and plays an important role in fast excitatory synaptic transmission by inducing long-term potentiation (By similarity). Binding of the excitatory neurotransmitter L-glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse upon entry of calcium (PubMed:17989220). The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist (PubMed:17989220). In the presence of CACNG8, shows resensitization which is characterized by a delayed accumulation of current flux upon continued application of glutamate (PubMed:21172611)
- Specific Function
- AMPA glutamate receptor activity
- 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]
Drug created at September 11, 2007 17:48 / Updated at August 26, 2024 19:24