Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H18N2O2 |
| Molecular Weight | 246.3049 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=CC(C)=C1NC(=O)CN2CCCC2=O
InChI
InChIKey=NGHTXZCKLWZPGK-UHFFFAOYSA-N
InChI=1S/C14H18N2O2/c1-10-5-3-6-11(2)14(10)15-12(17)9-16-8-4-7-13(16)18/h3,5-6H,4,7-9H2,1-2H3,(H,15,17)
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/10820661 | http://adisinsight.springer.com/drugs/800001382
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/10820661 | http://adisinsight.springer.com/drugs/800001382
Nefiracetam is a cyclic derivative of gamma-aminobutyric acid (GABA). It is thought to act by normalising dysfunctional acetylcholine, GABA and possibly monoamine neurotransmitter systems, but it may also facilitate N/L-type calcium channel opening. Nefiracetam has received attention as a treatment for seizures, depression, and dementia. Nefiracetam was found to be extremely testicular toxic in both rats and dogs; it was found to significantly decrease the levels of testicular testosterone leading to atrophy and malformation of sperm.
CNS Activity
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.97 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
2.08 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
22.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
4.02 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
0.68 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
10.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
4.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
19.59 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
16.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
167 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
27.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
5.67 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
78.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.86 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
4.78 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.77 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
3.33 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
4.43 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
3.85 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1360528 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFIRACETAM serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| major [Km 5618 uM] | ||||
| minor | ||||
| no | ||||
| yes [Km 442 uM] |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of N-(2,6-dimethylphenyl)-2-(2-oxo-1-pyrrolidinyl)acetamide (DM-9384) on learning and memory in rats. | 1989 May |
|
| Effects of DM-9384, a pyrrolidone derivative, on alcohol- and chlordiazepoxide-induced amnesia in mice. | 1990 Jun |
|
| Nefiracetam (DM-9384) reverses apomorphine-induced amnesia of a passive avoidance response: delayed emergence of the memory retention effects. | 1996 Jun |
|
| Nefiracetam prevents propofol-induced anterograde and retrograde amnesia in the rodent without compromising quality of anesthesia. | 1998 Sep |
|
| Nootropic drug modulation of neuronal nicotinic acetylcholine receptors in rat cortical neurons. | 2001 Apr |
|
| Quantitative effects of nefiracetam on spatial learning of rats after cerebral embolism. | 2001 May-Jun |
|
| Nefiracetam. DM 9384, DZL 221, Translon. | 2002 |
|
| Nefiracetam improves the impairment of local cerebral blood flow and glucose utilization after chronic focal cerebral ischemia in rats. | 2002 |
|
| The cognition-enhancer nefiracetam is protective in BDNF-independent neuronal cell death under the serum-free condition. | 2002 Feb |
|
| No spatial working memory deficit in beta-amyloid-exposed rats. A longitudinal study. | 2002 Jun |
|
| Nonopioid and neuropathy-specific analgesic action of the nootropic drug nefiracetam in mice. | 2002 Oct |
|
| The long-term effects of nefiracetam on learning in older rabbits. | 2002 Oct 17 |
|
| Effects of nefiracetam on spatial memory function and acetylcholine and GABA metabolism in microsphere-embolized rats. | 2002 Oct 18 |
|
| Impairment of contextual fear conditioning in rats by Group I mGluRs: reversal by the nootropic nefiracetam. | 2002 Sep |
|
| Unique mechanism of action of Alzheimer's drugs on brain nicotinic acetylcholine receptors and NMDA receptors. | 2003 Dec 5 |
|
| Effects of nefiracetam on cerebral adenylyl cyclase activity in rats with microsphere embolism-induced memory dysfunction. | 2003 Mar |
|
| Effect of nefiracetam, a neurotransmission enhancer, on primary uroepithelial cells of the canine urinary bladder. | 2003 Mar |
|
| The cognition-enhancer nefiracetam inhibits both necrosis and apoptosis in retinal ischemic models in vitro and in vivo. | 2004 Apr |
|
| Nefiracetam and physostigmine: separate and combined effects on learning in older rabbits. | 2004 Jul |
|
| Testicular toxicity induced in dogs by nefiracetam, a neutrotransmission enhancer. | 2004 May |
|
| Mechanisms of action of cognitive enhancers on neuroreceptors. | 2004 Nov |
|
| Negative regulation of opioid receptor-G protein-Ca2+ channel pathway by the nootropic nefiracetam. | 2004 Oct |
|
| Nefiracetam attenuates methamphetamine-induced discriminative stimulus effects in rats. | 2004 Oct |
|
| Nootropic nefiracetam inhibits proconvulsant action of peripheral-type benzodiazepines in epileptic mutant EL mice. | 2004 Oct |
|
| Early pathophysiological features in canine renal papillary necrosis induced by nefiracetam. | 2005 |
|
| Effects of nefiracetam on the levels of brain-derived neurotrophic factor and synapsin I mRNA and protein in the hippocampus of microsphere-embolized rats. | 2005 Jan 10 |
|
| [Evaluation methods for the discriminative stimulus and possible mechanisms of discriminative stimulus effects of methamphetamine in the rat]. | 2005 Jul |
|
| Anticonvulsant properties of the novel nootropic agent nefiracetam in seizure models of mice and rats. | 2005 Jun |
|
| Pre-injury administration of morphine prevents development of neuropathic hyperalgesia through activation of descending monoaminergic mechanisms in the spinal cord in mice. | 2005 Jun 3 |
|
| Effects of Nefiracetam, a novel pyrrolidone-type nootropic agent, on the amygdala-kindled seizures in rats. | 2005 Oct |
|
| Modulation of N-methyl-D-aspartate receptors by donepezil in rat cortical neurons. | 2005 Oct |
|
| Investigation on urinary proteins and renal mRNA expression in canine renal papillary necrosis induced by nefiracetam. | 2005 Sep |
|
| Anticonvulsant and neuroprotective effects of the novel nootropic agent nefiracetam on kainic acid-induced seizures in rats. | 2005 Sep 28 |
|
| Chronic exposure of rats to cognition enhancing drugs produces a neuroplastic response identical to that obtained by complex environment rearing. | 2006 Jan |
|
| Discriminative-stimulus effects of methamphetamine and morphine in rats are attenuated by cAMP-related compounds. | 2006 Oct 2 |
|
| Nefiracetam potentiates N-methyl-D-aspartate (NMDA) receptor function via protein kinase C activation and reduces magnesium block of NMDA receptor. | 2007 Feb |
|
| CaM kinase II and protein kinase C activations mediate enhancement of long-term potentiation by nefiracetam in the rat hippocampal CA1 region. | 2008 Aug |
|
| Influence of TRPV1 on diabetes-induced alterations in thermal pain sensitivity. | 2008 Mar 1 |
|
| Double-blind randomized treatment of poststroke depression using nefiracetam. | 2008 Spring |
|
| Improvement of depressive behaviors by nefiracetam is associated with activation of CaM kinases in olfactory bulbectomized mice. | 2009 Apr 10 |
|
| Nefiracetam activation of CaM kinase II and protein kinase C mediated by NMDA and metabotropic glutamate receptors in olfactory bulbectomized mice. | 2009 Jul |
|
| Nefiracetam and galantamine modulation of excitatory and inhibitory synaptic transmission via stimulation of neuronal nicotinic acetylcholine receptors in rat cortical neurons. | 2009 May 5 |
|
| Double-blind treatment of apathy in patients with poststroke depression using nefiracetam. | 2009 Spring |
|
| Trace eyeblink conditioning is impaired in α7 but not in β2 nicotinic acetylcholine receptor knockout mice. | 2010 |
|
| E22Δ Mutation in Amyloid β-Protein Promotes β-Sheet Transformation, Radical Production, and Synaptotoxicity, But Not Neurotoxicity. | 2010 Dec 19 |
|
| Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders. | 2010 Feb 12 |
|
| Essential role of neuron-enriched diacylglycerol kinase (DGK), DGKbeta in neurite spine formation, contributing to cognitive function. | 2010 Jul 15 |
|
| Apathy following stroke. | 2010 Jun |
|
| Synthesis of N-substituted Clausenamide analogues. | 2010 Nov |
Patents
Sample Use Guides
The recommended dosage lies between 8.721mg/kg and 29.072mg/kg in humans for treating the negative cognitive effects of seizures as well as treating severely depressed individuals
Route of Administration:
Oral
The effects of nefiracetam on GABA-induced chloride currents were studied with rat dorsal root ganglion neurons in primary culture using the whole-cell patch-clamp technique. The dose-response curve for GABA-induced currents was shifted by 16 uM to lower concentrations by 10 uM nefiracetam while the maximal response was reduced by 22.84 +/- 0.68%.
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NCI_THESAURUS |
C1509
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m7794
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SUB09181MIG
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C058876
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ACTIVE MOIETY
