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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
Structure of PIRACETAM

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)

HIDE SMILES / InChI

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

Description
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.

Originator

Sources: Zhurnal Obshchei Khimii, Volume31, Pages2595-9, Journal, 1961

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
99%
PIRACETAM serum
Homo sapiens
Doses

Doses

DosePopulationAdverse 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%)
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%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
Pharmacological treatment for aphasia following stroke.
2001
Pharmacokinetic considerations in prescribing antiepileptic drugs.
2001
[Current strategies of pathogenetic therapy of Alzheimer's disease].
2001
Levetiracetam add-on for drug-resistant localization related (partial) epilepsy.
2001
Restitution of alpha-topography by piracetam in post-stroke aphasia.
2001 Apr
Levetiracetam psychosis in children with epilepsy.
2001 Dec
Pharmacokinetic study of levetiracetam in children.
2001 Dec
Piracetam affects facilitatory I-wave interaction in the human motor cortex.
2001 Feb
Levetiracetam.
2001 Jul 1
[Piracetam in the treatment of a patient with idiopathic cortical myoclonus].
2001 Jul 16-31
Levetiracetam inhibits the high-voltage-activated Ca(2+) current in pyramidal neurones of rat hippocampal slices.
2001 Jun 22
Piracetam in post-hypoxic action myoclonus.
2001 Nov
Levetiracetam: a novel antiepileptic drug.
2001 Nov
A systematic review of the safety profile of levetiracetam: a new antiepileptic drug.
2001 Nov
Lack of effect of repeated administration of levetiracetam on the pharmacodynamic and pharmacokinetic profiles of warfarin.
2001 Nov
[Effect of piracetam on the conditional reflex memory under probable reinforcement conditions].
2001 Nov-Dec
Controlled pilot study of piracetam for pediatric opsoclonus-myoclonus.
2001 Nov-Dec
Piracetam study: poorly designed and misinterpreted.
2001 Oct
The nootropic drug vinpocetine inhibits veratridine-induced [Ca2+]i increase in rat hippocampal CA1 pyramidal cells.
2001 Sep
Effect of levetiracetam on human corticospinal excitability.
2001 Sep 11
[Treatment and long-term follow-up of post-anoxic myoclonus].
2001 Sep 23
[Managing vertigo and vertigo syndromes in the elderly].
2001 Sep 8-15
Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug.
2001 Winter
Piracetam for fetal distress in labour.
2002
[Piracetam in combined pathogenetic therapy of recurrent duodenal ulcer].
2002
Design and study of piracetam-like nootropics, controversial members of the problematic class of cognition-enhancing drugs.
2002
A new antiepileptic drug.
2002 Apr
Carbamazepine toxicity during combination therapy with levetiracetam: a pharmacodynamic interaction.
2002 Feb
Levetiracetam: a different approach to the pharmacotherapy of epilepsy.
2002 Feb
Three new drugs for epilepsy: levetiracetam, oxcarbazepine, and zonisamide.
2002 Jan
Selective blockade of N-type calcium channels by levetiracetam.
2002 Jan
Dose-response effect of levetiracetam 1000 and 2000 mg/day in partial epilepsy.
2002 Jan
Newer therapies in the drug treatment of epilepsy.
2002 Jan
[Scavenger effect of various cerebrovascular drugs].
2002 Jan 6
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
[Levetiracetam: an anti-epileptic drug with interesting pharmacokinetic properties].
2002 Jun 29
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
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

Patents

Sample Use Guides

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
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 Mon Mar 31 18:45:54 GMT 2025
Edited
by admin
on Mon Mar 31 18:45:54 GMT 2025
Record UNII
ZH516LNZ10
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRACETAM
EP   HSDB   INCI   INN   JAN   MART.   MI   USAN   WHO-DD  
INCI   USAN   INN  
Official Name English
MYOCALM
Preferred Name English
PIRACETAM [HSDB]
Common Name English
piracetam [INN]
Common Name English
PIRACETAM [MI]
Common Name English
PIRACETAM [EP MONOGRAPH]
Common Name English
NSC-758191
Code English
PIRACETAM [MART.]
Common Name English
PIRACETAM [USAN]
Common Name English
PIRACETAM [WHO-DD]
Common Name English
PIRACETAM [JAN]
Common Name English
CL-871
Code English
Classification Tree Code System Code
WHO-VATC QN06BX03
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
DSLD 4054 (Number of products:5)
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
WHO-ATC N06BX03
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
FDA ORPHAN DRUG 20987
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
NCI_THESAURUS C1509
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
Code System Code Type Description
HSDB
7529
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
NCI_THESAURUS
C66410
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
CAS
7491-74-9
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
SMS_ID
100000091987
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
ECHA (EC/EINECS)
231-312-7
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
MESH
D010889
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
RXCUI
8351
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY RxNorm
PUBCHEM
4843
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
NSC
758191
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
EPA CompTox
DTXSID5044491
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
FDA UNII
ZH516LNZ10
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
INN
2687
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
DRUG BANK
DB09210
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
ChEMBL
CHEMBL36715
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
DRUG CENTRAL
2197
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
WIKIPEDIA
PIRACETAM
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
EVMPD
SUB09892MIG
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
MERCK INDEX
m8870
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY Merck Index
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