PZI

2-(2-oxopyrrolidin-1-yl)acetamide


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Chemical Component Summary

Name2-(2-oxopyrrolidin-1-yl)acetamide
Identifiers2-(2-oxopyrrolidin-1-yl)ethanamide
FormulaC6 H10 N2 O2
Molecular Weight142.156
TypeNON-POLYMER
Isomeric SMILESC1CC(=O)N(C1)CC(=O)N
InChIInChI=1S/C6H10N2O2/c7-5(9)4-8-3-1-2-6(8)10/h1-4H2,(H2,7,9)
InChIKeyGMZVRMREEHBGGF-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count20
Chiral Atom Count0
Bond Count20
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB09210 
NamePiracetam
Groups
  • approved
  • investigational
DescriptionPiracetam 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 and is a cyclic derivative of the neurotransmitter γ-aminobutyric acid (GABA). However its mechanism of action differ from that of endogenous GABA. Piracetam has neuroprotective and anticonvulsant properties and is reported to improve neural plasticity [A31532]. Its efficacy is documented in cognitive disorders and dementia, vertigo, cortical myoclonus, dyslexia, and sickle cell anemia although the clinical application in these conditions is not yet established. Piracetam has effects on the vascular system by reducing erythrocyte adhesion to the vascular endothelium, hindering vasospasms and facilitating microcirculation [A31532]. Originally marketed by UCB Pharma in 1971, piracetam was the first nootropic drug to modulate cognitive function without causing sedation or stimulation [A31532]. It is not approved for any medical or dietary use by the FDA. In the UK, piracetam is prescribed mainly for myoclonus, but is used off-label for other conditions such as learning difficulties in children, memory loss or other cognitive defects in the elderly, and sickle-cell vaso-occlusive crises [L1124]. Evidence to support its use for many conditions is unclear.
Synonyms
  • Piracetamum
  • Piracetam
IndicationIndicated in adult patients suffering from myoclonus of cortical origin, irrespective of aetiology, and should be used in combination with other anti-myoclonic therapies [L1125].
Categories
  • Acetamides
  • Acetates
  • Acids, Acyclic
  • Amides
  • Central Nervous System Agents
ATC-CodeN06BX03
CAS number7491-74-9

Related Resource References

Resource NameReference
PubChem 4843
ChEMBL CHEMBL36715
ChEBI CHEBI:32010
CCDC/CSD BISMEV11, YAKWAJ01, BISMEV12, RUCDUP, BISMEV03, BISMEV13, FIXROV, LIFNOE, RUCFAX, FIXROV01, XOZSOV, YAKWAJ, LATBOZ, DAVPAS, ABORAM, DAVPEW, BISMEV02, BISMEV04, DEDMAD, AKISEU, BISMEV, BISMEV01, RUCFEB, BISMEV08, BISMEV07, BISMEV09, BISMEV10, KEBMAJ
COD 2101279, 4500780, 4500782, 4500781, 4501376, 7203722, 7203723, 4504083, 4504084, 4504085, 4504087, 4504086, 4504088, 2105048, 7111484, 7207675, 2311902, 2100167, 2100168, 2100169, 2100172, 2100170, 2100173, 2100171, 2100174, 2100175, 2100176, 2100177, 2100178, 2100179, 2100180, 2100181, 2100182, 2100312, 2100313, 2100314, 2100315, 2100316, 2100317, 2100318, 2100319, 2100320, 2100321, 2100322, 2100324, 2100323, 2100325, 2100326, 2100327