Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H10N2O2 |
Molecular Weight | 142.1558 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)CN1CCCC1=O
InChI
InChIKey=GMZVRMREEHBGGF-UHFFFAOYSA-N
InChI=1S/C6H10N2O2/c7-5(9)4-8-3-1-2-6(8)10/h1-4H2,(H2,7,9)
Molecular Formula | C6H10N2O2 |
Molecular Weight | 142.1558 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.drugbank.ca/drugs/DB09210Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20163115 | https://www.ncbi.nlm.nih.gov/pubmed/16459490 | https://www.ncbi.nlm.nih.gov/pubmed/10210031 | https://www.drugs.com/uk/piracetam-800mg-tablets-leaflet.html | https://www.ncbi.nlm.nih.gov/pubmed/16007238 | https://www.ncbi.nlm.nih.gov/pubmed/17284293
Sources: https://www.drugbank.ca/drugs/DB09210
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20163115 | https://www.ncbi.nlm.nih.gov/pubmed/16459490 | https://www.ncbi.nlm.nih.gov/pubmed/10210031 | https://www.drugs.com/uk/piracetam-800mg-tablets-leaflet.html | https://www.ncbi.nlm.nih.gov/pubmed/16007238 | https://www.ncbi.nlm.nih.gov/pubmed/17284293
Piracetam (sold under many brand names) is a nootropic drug in the racetams group, with chemical name 2-oxo-1-pyrrolidine acetamide. It shares the same 2-oxo-pyrrolidone base structure with pyroglutamic acid. Piracetam is a cyclic derivative of the neurotransmitter gamma-aminobutyric acid (GABA), originally marketed in 1971 by UCB Pharma. Presently piracetam is used in many European countries, Asia and South America. In the United States, it is not approved by the US Food and Drug Administration for any medical use and it is not permitted to be sold as a dietary supplement. In the UK, piracetam is prescribed mainly for myoclonus but is used off-label for other conditions. Evidence to support its use for many conditions is unclear. Piracetam's mechanism of action, as with racetams in general, is not fully understood. The drug influences neuronal and vascular functions and influences cognitive function without acting as a sedative or stimulant. It is hypothesized to act on ion channels or ion carriers, thus leading to increased neuron excitability. GABA brain metabolism and GABA receptors are not affected by piracetam. It has been found to increase blood flow and oxygen consumption in parts of the brain, but this may be a side effect of increased brain activity rather than a primary effector mechanism of action for the drug.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2009 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20163115 |
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Target ID: CHEMBL3503 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20163115 |
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Target ID: CHEMBL3504 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20163115 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Nootropil Approved UseUnknown |
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Primary | Nootropil Approved UseUnknown |
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Preventing | Nootropil Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
85.3 μg/mL |
3200 mg single, oral dose: 3200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
173.7 μg/mL |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
177 μg/mL |
6400 mg 3 times / day steady-state, oral dose: 6400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
211.2 μg/mL |
6400 mg 3 times / day steady-state, oral dose: 6400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
173.7 μg/mL |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
136.5 μg/mL |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
521.7 μg × h/mL |
3200 mg single, oral dose: 3200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1192.5 μg × h/mL |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1590.1 μg × h/mL |
6400 mg 3 times / day steady-state, oral dose: 6400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1661.7 μg × h/mL |
6400 mg 3 times / day steady-state, oral dose: 6400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1192.5 μg × h/mL |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1199.3 μg × h/mL |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.6 h |
3200 mg single, oral dose: 3200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.6 h |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5 h |
6400 mg 3 times / day steady-state, oral dose: 6400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5 h |
6400 mg 3 times / day steady-state, oral dose: 6400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.6 h |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.2 h |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
99% |
PIRACETAM serum | Homo sapiens |
Doses
Dose | Population | Adverse events |
---|---|---|
12 g 2 times / day multiple, oral Highest studied dose Dose: 12 g, 2 times / day Route: oral Route: multiple Dose: 12 g, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Stomach upset, Ulcer... AEs leading to discontinuation/dose reduction: Stomach upset (6.6%) Sources: Ulcer (0.4%) Eczema (0.4%) Allergy (0.4%) Cerebral seizures (0.4%) Depression (0.4%) Heartburn (0.4%) Gastritis (0.4%) Weight increase (0.4%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Allergy | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Cerebral seizures | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Depression | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Eczema | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Gastritis | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Heartburn | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Ulcer | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Weight increase | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Stomach upset | 6.6% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Pharmacological treatment for aphasia following stroke. | 2001 |
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Pharmacokinetic considerations in prescribing antiepileptic drugs. | 2001 |
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[Current strategies of pathogenetic therapy of Alzheimer's disease]. | 2001 |
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Levetiracetam add-on for drug-resistant localization related (partial) epilepsy. | 2001 |
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Restitution of alpha-topography by piracetam in post-stroke aphasia. | 2001 Apr |
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Levetiracetam psychosis in children with epilepsy. | 2001 Dec |
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Pharmacokinetic study of levetiracetam in children. | 2001 Dec |
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Piracetam affects facilitatory I-wave interaction in the human motor cortex. | 2001 Feb |
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Levetiracetam. | 2001 Jul 1 |
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[Piracetam in the treatment of a patient with idiopathic cortical myoclonus]. | 2001 Jul 16-31 |
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Levetiracetam inhibits the high-voltage-activated Ca(2+) current in pyramidal neurones of rat hippocampal slices. | 2001 Jun 22 |
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Piracetam in post-hypoxic action myoclonus. | 2001 Nov |
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Levetiracetam: a novel antiepileptic drug. | 2001 Nov |
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A systematic review of the safety profile of levetiracetam: a new antiepileptic drug. | 2001 Nov |
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Lack of effect of repeated administration of levetiracetam on the pharmacodynamic and pharmacokinetic profiles of warfarin. | 2001 Nov |
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[Effect of piracetam on the conditional reflex memory under probable reinforcement conditions]. | 2001 Nov-Dec |
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Controlled pilot study of piracetam for pediatric opsoclonus-myoclonus. | 2001 Nov-Dec |
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Piracetam study: poorly designed and misinterpreted. | 2001 Oct |
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The nootropic drug vinpocetine inhibits veratridine-induced [Ca2+]i increase in rat hippocampal CA1 pyramidal cells. | 2001 Sep |
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Effect of levetiracetam on human corticospinal excitability. | 2001 Sep 11 |
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[Treatment and long-term follow-up of post-anoxic myoclonus]. | 2001 Sep 23 |
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[Managing vertigo and vertigo syndromes in the elderly]. | 2001 Sep 8-15 |
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Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug. | 2001 Winter |
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Piracetam for fetal distress in labour. | 2002 |
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[Piracetam in combined pathogenetic therapy of recurrent duodenal ulcer]. | 2002 |
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Design and study of piracetam-like nootropics, controversial members of the problematic class of cognition-enhancing drugs. | 2002 |
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A new antiepileptic drug. | 2002 Apr |
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Carbamazepine toxicity during combination therapy with levetiracetam: a pharmacodynamic interaction. | 2002 Feb |
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Levetiracetam: a different approach to the pharmacotherapy of epilepsy. | 2002 Feb |
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Three new drugs for epilepsy: levetiracetam, oxcarbazepine, and zonisamide. | 2002 Jan |
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Selective blockade of N-type calcium channels by levetiracetam. | 2002 Jan |
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Dose-response effect of levetiracetam 1000 and 2000 mg/day in partial epilepsy. | 2002 Jan |
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Newer therapies in the drug treatment of epilepsy. | 2002 Jan |
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[Scavenger effect of various cerebrovascular drugs]. | 2002 Jan 6 |
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In vitro antioxidant properties of pentoxifylline, piracetam, and vinpocetine. | 2002 Jan-Feb |
|
Aggravation of partial seizures by antiepileptic drugs: is there evidence from clinical trials? | 2002 Jul 9 |
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[Levetiracetam: an anti-epileptic drug with interesting pharmacokinetic properties]. | 2002 Jun 29 |
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A comparison of the efficacy of carbamazepine and the novel anti-epileptic drug levetiracetam in the tetanus toxin model of focal complex partial epilepsy. | 2002 Mar |
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Levetiracetam opposes the action of GABAA antagonists in hypothalamic neurones. | 2002 Mar |
|
[Effect of the novel dipeptide nootropic agent noopept and its metabolite cyclo-L-prolylglycine on the transcallosal evoked potential in the rat brain]. | 2002 Mar-Apr |
|
[Experimental and clinical rationale for complex treatment of mental disorders in clean-up workers of the Chernobyl nuclear plant accident]. | 2002 Mar-Apr |
|
Piracetam and vinpocetine exert cytoprotective activity and prevent apoptosis of astrocytes in vitro in hypoxia and reoxygenation. | 2002 May |
|
Brain neurotransmitter receptor binding and nootropic studies on Indian Hypericum perforatum Linn. | 2002 May |
|
Levetiracetam in the treatment of paroxysmal kinesiogenic choreoathetosis. | 2002 May |
|
[Levetiracetam: a molecule with a novel mechanism of action in the pharmaceutical treatment of epilepsy]. | 2002 May 20 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16007238
The dosing of piracetam varies according to indication. For cognitive disorders and vertigo it is 2.4–4.8 g daily p.o., for dyslexia it is 3.2 g daily p.o., for cortical myoclonus it is 7.2–24.0 g daily p.o., for prophylaxis of vaso-occlusive crises in sickle cell anemia it is 160 mg/kg/day p.o., and for remission of vaso-occlusive crises it is 300 mg/kg/day i.v. in four divided doses.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17284293
Primary cultures of mice cortical neurons were washed twice in glucose-free Earle’s solution (143 mM NaCl, 5.4 mM KCl, 1.8 mM CaCl2, 1.0 mM MgSO4, 1.0 mM NaH2PO4, 2.4 mM HEPES, and pH 7.4) at 37 OC and placed in an incubator containing 95 % N2 and 5 % CO2 for 4 h. The neurons were then fed with high glucose DMEM (Earle’s solution), and returned to the normal incubator for a 4 h recovery. Those neurons for control underwent the same procedure except the oxygen/glucose deprivation treatment. For the drug treatment groups, piracetam (PIR, 500 or 1,000 mkM/l) or nimodipine (NIMO, 10 mkM/l) was given 12 h before OGD or during OGD and for the following 4 h. The OGD control group was treated with vehicle (PBS).
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:45:54 GMT 2025
by
admin
on
Mon Mar 31 18:45:54 GMT 2025
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Record UNII |
ZH516LNZ10
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QN06BX03
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DSLD |
4054 (Number of products:5)
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WHO-ATC |
N06BX03
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FDA ORPHAN DRUG |
20987
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NCI_THESAURUS |
C1509
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7529
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C66410
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7491-74-9
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100000091987
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231-312-7
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D010889
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8351
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4843
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758191
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DTXSID5044491
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ZH516LNZ10
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2687
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DB09210
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CHEMBL36715
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2197
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PIRACETAM
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SUB09892MIG
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m8870
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PRIMARY | Merck Index |
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TARGET->POSITIVE ALLOSTERIC MODULATOR (PAM) |
This action is very weak and its clinical effects may not necessarily be mediated by this action.
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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