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)
DescriptionSources: http://www.smarternootropics.com/nefiracetam/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
Sources: http://www.smarternootropics.com/nefiracetam/
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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2855 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17095583 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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 DM-9384, a pyrrolidone derivative, on alcohol- and chlordiazepoxide-induced amnesia in mice. | 1990 Jun |
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Nefiracetam metabolism by human liver microsomes: role of cytochrome P450 3A4 and cytochrome P450 1A2 in 5-hydroxynefiracetam formation. | 2001 Jun |
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Nefiracetam improves the impairment of local cerebral blood flow and glucose utilization after chronic focal cerebral ischemia in rats. | 2002 |
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Nefiracetam ameliorates associative learning impairment in the scopolamine-injected older rabbit. | 2002 Apr |
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Nefiracetam. Daiichi Seiyaku. | 2002 May |
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Effects of nefiracetam on spatial memory function and acetylcholine and GABA metabolism in microsphere-embolized rats. | 2002 Oct 18 |
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Effects of nefiracetam on cerebral adenylyl cyclase activity in rats with microsphere embolism-induced memory dysfunction. | 2003 Mar |
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Negative regulation of opioid receptor-G protein-Ca2+ channel pathway by the nootropic nefiracetam. | 2004 Oct |
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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 |
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Modulation of N-methyl-D-aspartate receptors by donepezil in rat cortical neurons. | 2005 Oct |
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Anticonvulsant and neuroprotective effects of the novel nootropic agent nefiracetam on kainic acid-induced seizures in rats. | 2005 Sep 28 |
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Nefiracetam potentiates N-methyl-D-aspartate (NMDA) receptor function via protein kinase C activation and reduces magnesium block of NMDA receptor. | 2007 Feb |
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Double-blind randomized treatment of poststroke depression using nefiracetam. | 2008 Spring |
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Essential role of neuron-enriched diacylglycerol kinase (DGK), DGKbeta in neurite spine formation, contributing to cognitive function. | 2010 Jul 15 |
|
Synthesis of N-substituted Clausenamide analogues. | 2010 Nov |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.smarternootropics.com/nefiracetam/
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9014140
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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ACTIVE MOIETY