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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.

CNS Activity

Originator

Kleev, B.V.|Smushkevich, Yu. I.|Gol'dovskii, A.E.
1
Sources: Zhurnal Obshchei Khimii, Volume31, Pages2595-9, Journal, 1961

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Positive Allosteric Modulator
179
Positive Allosteric Modulator
179
Positive Allosteric Modulator
179
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Nootropil

Approved Use

Unknown
Primary
Approved
8429
Nootropil

Approved Use

Unknown
Preventing
Approved
8429
Nootropil

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Levetiracetam psychosis in children with epilepsy.
2001 Dec
Pharmacokinetic study of levetiracetam in children.
2001 Dec
Effect of levetiracetam in patients with epilepsy and interictal epileptiform discharges.
2001 Dec
Improving effects of SSF on memory deficits and pathological changes of neural and immunological systems in senescent mice.
2001 Dec
Pyrrolidone derivatives.
2001 Dec 1
Piracetam in post-hypoxic action myoclonus.
2001 Nov
[Levetiracetam].
2001 Nov
Levetiracetam: a novel antiepileptic drug.
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
Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug.
2001 Winter
Clinical efficacy of piracetam in cognitive impairment: a meta-analysis.
2002
The clinical challenge of posthypoxic myoclonus.
2002
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
Levetiracetam--a new drug for epilepsy.
2002 Apr
Effects of the novel antiepileptic drug levetiracetam on spontaneous recurrent seizures in the rat pilocarpine model of temporal lobe epilepsy.
2002 Apr
A new antiepileptic drug.
2002 Apr
Antidepressant activity of memory-enhancing drugs in the reduction of submissive behavior model.
2002 Apr 5
Neuroprotective agents in acute ischemic stroke.
2002 Feb
Breath holding spells in a 3-day-old neonate: an unusual early presentation in a family with a history of breath holding spells.
2002 Feb
Carbamazepine toxicity during combination therapy with levetiracetam: a pharmacodynamic interaction.
2002 Feb
Levetiracetam: a different approach to the pharmacotherapy of epilepsy.
2002 Feb
Using the new antiepilepsy drugs in children.
2002 Jan
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
Levetiracetam for acute mania.
2002 Jan
[Scavenger effect of various cerebrovascular drugs].
2002 Jan 6
[Anti-arrhythmic properties of GABA and GABA-ergic system activators].
2002 Jan-Feb
In vitro antioxidant properties of pentoxifylline, piracetam, and vinpocetine.
2002 Jan-Feb
Levetiracetam does not alter the pharmacokinetics of an oral contraceptive in healthy women.
2002 Jul
The anti-epileptic drug levetiracetam reverses the inhibition by negative allosteric modulators of neuronal GABA- and glycine-gated currents.
2002 Jul
Aggravation of partial seizures by antiepileptic drugs: is there evidence from clinical trials?
2002 Jul 9
DM235 (sunifiram): a novel nootropic with potential as a cognitive enhancer.
2002 Jun
[Levetiracetam: an anti-epileptic drug with interesting pharmacokinetic properties].
2002 Jun 29
Suppression of cortical myoclonus by levetiracetam.
2002 Mar
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
The new antiepileptic drug levetiracetam normalises chlordiazepoxide withdrawal-induced anxiety in mice.
2002 Mar 29
[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
Efficacy and safety of levetiracetam in children with partial seizures: an open-label trial.
2002 May
[Effects of piracetam on the cognitive functions verified by electrophysiologic methods].
2002 May 19
[Levetiracetam: a molecule with a novel mechanism of action in the pharmaceutical treatment of epilepsy].
2002 May 20
Patents

Patents

07786132
8

Sample Use Guides

In Vivo Use Guide
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
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 Fri Dec 15 17:24:27 UTC 2023
Edited
by admin
on Fri Dec 15 17:24:27 UTC 2023
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
PIRACETAM [HSDB]
Common Name English
piracetam [INN]
Common Name English
PIRACETAM [MI]
Common Name English
PIRACETAM [INCI]
Common Name English
PIRACETAM [EP MONOGRAPH]
Common Name English
NSC-758191
Code English
PIRACETAM [MART.]
Common Name English
PIRACETAM [USAN]
Common Name English
MYOCALM
Brand 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 Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
DSLD 4054 (Number of products:5)
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
WHO-ATC N06BX03
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
FDA ORPHAN DRUG 20987
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
NCI_THESAURUS C1509
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
Code System Code Type Description
HSDB
7529
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
NCI_THESAURUS
C66410
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
CAS
7491-74-9
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
SMS_ID
100000091987
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
ECHA (EC/EINECS)
231-312-7
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
MESH
D010889
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
RXCUI
8351
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY RxNorm
PUBCHEM
4843
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PRIMARY
NSC
758191
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PRIMARY
EPA CompTox
DTXSID5044491
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
FDA UNII
ZH516LNZ10
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
INN
2687
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
DRUG BANK
DB09210
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
ChEMBL
CHEMBL36715
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
DRUG CENTRAL
2197
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
WIKIPEDIA
PIRACETAM
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
EVMPD
SUB09892MIG
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY
MERCK INDEX
m8870
Created by admin on Fri Dec 15 17:24:27 UTC 2023 , Edited by admin on Fri Dec 15 17:24:27 UTC 2023
PRIMARY Merck Index
Related Record Type Details
AMPA-SELECTIVE GLUTAMATE RECEPTOR 2
TARGET->POSITIVE ALLOSTERIC MODULATOR (PAM)
This action is very weak and its clinical effects may not necessarily be mediated by this action.
Related Record Type Details
Structure of PIRACETAM
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