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Chemistry

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Also known as: 7491-74-9, 2-(2-oxopyrrolidin-1-yl)acetamide, Nootropil, 2-oxo-1-pyrrolidineacetamide, Nootropyl, Pyracetam
Molecular Formula
C6H10N2O2
Molecular Weight
142.16  g/mol
InChI Key
GMZVRMREEHBGGF-UHFFFAOYSA-N
FDA UNII
ZH516LNZ10

Piracetam
A compound suggested to be both a nootropic and a neuroprotective agent.
1 2D Structure

Piracetam

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(2-oxopyrrolidin-1-yl)acetamide
2.1.2 InChI
InChI=1S/C6H10N2O2/c7-5(9)4-8-3-1-2-6(8)10/h1-4H2,(H2,7,9)
2.1.3 InChI Key
GMZVRMREEHBGGF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CC(=O)N(C1)CC(=O)N
2.2 Other Identifiers
2.2.1 UNII
ZH516LNZ10
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-pyrrolidone-n-acetamide

2. Avigilen

3. Axonyl

4. Cerebroforte

5. Cerepar N

6. Ciclofalina

7. Cuxabrain

8. Dinagen

9. Gabacet

10. Geram

11. Memo Puren

12. Memo-puren

13. Nootrop

14. Nootropil

15. Nootropyl

16. Normabran

17. Piracebral

18. Piracetam Abz

19. Piracetam Rph

20. Piracetam-rph

21. Piracetrop

22. Pirazetam

23. Pyracetam

24. Pyramem

25. Sinapsan

26. Ucb 6215

27. Ucb-6215

28. Ucb6215

2.3.2 Depositor-Supplied Synonyms

1. 7491-74-9

2. 2-(2-oxopyrrolidin-1-yl)acetamide

3. Nootropil

4. 2-oxo-1-pyrrolidineacetamide

5. Nootropyl

6. Pyracetam

7. 1-pyrrolidineacetamide, 2-oxo-

8. Normabrain

9. Gabacet

10. Pyramem

11. 2-pyrrolidinoneacetamide

12. Genogris

13. Pirroxil

14. Euvifor

15. Nootron

16. Myocalm

17. 2-oxo-pyrrolidine Acetamide

18. 2-pyrrolidoneacetamide

19. Cl-871

20. Ucb 6215

21. Ucb-6215

22. 2-(2-oxo-pyrrolidin-1-yl)acetamide

23. 2-oxo-pyrrolidin-1-ylacetamide

24. 2-ketopyrrolidine-1-ylacetamide

25. 2-(2-oxopyrrolidino)acetamide

26. Mls000069719

27. 2-(2-oxo-1-pyrrolidinyl)acetamide

28. Ciclofalina

29. Nsc-758191

30. Smr000058196

31. Zh516lnz10

32. Pirazetam

33. Ncgc00015821-02

34. Cas-7491-74-9

35. Dsstox_cid_24491

36. Dsstox_rid_80267

37. Dsstox_gsid_44491

38. Naofukang [chinese]

39. Cerebroforte

40. Piracetamum

41. Avigilen

42. Breinox

43. Naofukang

44. Nootrop

45. Norzetam

46. Axonyl

47. Geram

48. Piracetamum [inn-latin]

49. Kt-801

50. Sr-01000076071

51. Einecs 231-312-7

52. Brn 1526393

53. Unii-zh516lnz10

54. Encetrop

55. Piracetam [usan:inn:ban]

56. Hsdb 7529

57. Piracetam,(s)

58. Prestwick_870

59. Myocalm (tn)

60. Deshydroxy Oxiracetam

61. Spectrum_001421

62. Piracetam [inn]

63. Piracetam [jan]

64. Piracetam [mi]

65. Piracetam [hsdb]

66. Piracetam [inci]

67. Piracetam [usan]

68. Opera_id_1766

69. Prestwick0_000537

70. Prestwick1_000537

71. Prestwick2_000537

72. Prestwick3_000537

73. Spectrum2_001074

74. Spectrum3_001523

75. Spectrum4_000742

76. Spectrum5_001037

77. Lopac-p-5295

78. Piracetam [mart.]

79. Cid_4843

80. Piracetam [who-dd]

81. Lopac0_000949

82. Oprea1_512927

83. Schembl20172

84. Bspbio_000553

85. Bspbio_002906

86. Kbiogr_001064

87. Kbioss_001901

88. 5-21-06-00360 (beilstein Handbook Reference)

89. Piracetam (jan/usan/inn)

90. 2-oxo-1-pyrrolidinylacetamide

91. Chembl36715

92. Divk1c_000259

93. Spectrum1502195

94. Spbio_001088

95. Spbio_002474

96. 2-(2-ketopyrrolidino)acetamide

97. Bpbio1_000609

98. Gtpl4288

99. Dtxsid5044491

100. Piracetam [ep Monograph]

101. Bdbm62877

102. Chebi:32010

103. Cl-781

104. Hms500m21

105. Kbio1_000259

106. Kbio2_001901

107. Kbio2_004469

108. Kbio2_007037

109. Kbio3_002406

110. Ninds_000259

111. Hms1569l15

112. Hms1921l12

113. Hms2092d18

114. Hms2096l15

115. Hms2230b24

116. Hms3262n20

117. Hms3371g01

118. Hms3657a05

119. Hms3713l15

120. Hms3885i07

121. Pharmakon1600-01502195

122. Bcp28414

123. Hy-b0585

124. Zinc3812874

125. Tox21_110229

126. Tox21_301990

127. Tox21_500949

128. Bbl028161

129. Ccg-39282

130. Nsc758191

131. S3070

132. Stk535612

133. 2 - Oxo - 1 - Pyrrolidineacetamide

134. Akos001038683

135. Tox21_110229_1

136. 2-(2-oxo-1-pyrrolidinyl)acetamide #

137. Db09210

138. Lp00949

139. Nsc 758191

140. Sdccgsbi-0050923.p004

141. Idi1_000259

142. Ncgc00015821-01

143. Ncgc00015821-03

144. Ncgc00015821-04

145. Ncgc00015821-05

146. Ncgc00015821-06

147. Ncgc00015821-07

148. Ncgc00015821-08

149. Ncgc00015821-10

150. Ncgc00015821-21

151. Ncgc00094253-01

152. Ncgc00094253-02

153. Ncgc00094253-03

154. Ncgc00094253-04

155. Ncgc00255727-01

156. Ncgc00261634-01

157. Ac-33158

158. As-13920

159. Bp166248

160. Sbi-0050923.p003

161. Db-019407

162. Ab00052287

163. Eu-0100949

164. Ft-0636504

165. P2880

166. Sw196995-3

167. 2-(2-oxidanylidenepyrrolidin-1-yl)ethanamide

168. Piracetam, Vetranal(tm), Analytical Standard

169. D01914

170. P 5295

171. Ab00052287_12

172. A838261

173. Ae-641/30117005

174. Q410069

175. Sr-01000076071-1

176. Sr-01000076071-4

177. Sr-01000076071-6

178. W-104408

179. Brd-k19456237-001-22-7

180. Z56865289

181. Piracetam, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 142.16 g/mol
Molecular Formula C6H10N2O2
XLogP3-1.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass142.074227566 g/mol
Monoisotopic Mass142.074227566 g/mol
Topological Polar Surface Area63.4 Ų
Heavy Atom Count10
Formal Charge0
Complexity167
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/Investigators/ report on a 30-year-old patient with advanced cerebellar degeneration due to sickle cell amemia 2. He presented with severe myoclonus, which was resistant to conventional therapy and dramatically improved after administration of 12-18 g/day piracetam. Piracetam may be considered in the treatment of refractory myoclonus in spinocerebellar degenerations.

PMID:16149096 De Rosa A et al; Mov Disord 21 (1): 116-8 (2006)


/Piracetam/ is indicated for patients suffering from myoclonus of cortical origin, irrespective of etiology, and should be used in combination with other anti-myoclonic therapies.

Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/


4.2 Drug Warning

Piracetam is contraindicated in patients with severe renal impairment (renal creatinine clearance of less than 20 mL per minute), hepatic impairment and to those under 16 years of age.

Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/


Piracetam is contraindicated in patients with cerebral hemorrhage and in those with hypersensitivity to piracetam, other pyrrolidone derivatives or any of the excipients.

Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/


Due to the effect of piracetam on platelet aggregation, caution is recommended in patients with underlying disorders of hemostasis, major surgery or severe hemorrhage.

Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/


Abrupt discontinuation of treatment should be avoided as this may induce myoclonic or generalised seizures in some myoclonic patients.

Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/


For more Drug Warnings (Complete) data for PIRACETAM (9 total), please visit the HSDB record page.


4.3 Drug Indication

Indicated in adult patients suffering from myoclonus of cortical origin, irrespective of aetiology, and should be used in combination with other anti-myoclonic therapies.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Piracetam is known to mediate various pharmacodynamic actions: **Neuronal effects**: Piracetam modulates the cholinergic, serotonergic, noradrenergic, and glutamatergic neurotransmission although the drug does not display high affinity to any of the associated receptors (Ki >10M). Instead, piracetam increases the density of postsynaptic receptors and/or restore the function of these receptors through stabilizing the membrane fluidity. In the forebrain of aging mice, the density of NMDA receptors was increased by approximately 20% following 14 days of piracetam treatment. Based on the findings of various animal and human studies, the cognitive processses including learning, memory, attention and consciousness were enhanced from piracetam therapy without inducing sedation and psychostimulant effects. Piracetam mediate neuroprotective effects against hypoxia-induced damage, intoxication, and electroconvulsive therapy. In two studies involving alcohol-treated rats with evidences of withdrawal-related neuronal loss, piracetam was shown to reduce the extent of neuronal loss and increase the numbers of synapses in the hippocampus by up to 20% relative to alcohol-treated or alcohol-withdrawn rats. This suggests that piracetam is capable in promoting neuroplasticity when recoverable neural circuits are present. Although the mechanism of action is not fully understood, administration of piracetam prior to a convulsant stimulus reduces the seizure severity and enhances the anticonvulsant effectiveness of conventional antiepileptics such as carbamazepine and diazepam. **Vascular effects**: Piracetam is shown to increase the deformability of erythrocytes, reduce platelet aggregation in a dose-dependent manner, reduce the adhesion of erythrocytes to vascular endothelium and capillary vasospasm. In healthy volunteers, piracetam mediated a direct stimulant effect on prostacycline synthesis and reduced the plasma levels of fibrinogen and von Willebrands factors (VIII: C; VIII R: AG; VIII R: vW) by 30 to 40%. Potentiated microcirculation is thought to arise from a combination of effects on erythrocytes, blood vessels and blood coagulation.


5.2 MeSH Pharmacological Classification

Nootropic Agents

Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. (See all compounds classified as Nootropic Agents.)


Neuroprotective Agents

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)


5.3 ATC Code

N06BX03

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N06 - Psychoanaleptics

N06B - Psychostimulants, agents used for adhd and nootropics

N06BX - Other psychostimulants and nootropics

N06BX03 - Piracetam


5.4 Absorption, Distribution and Excretion

Absorption

Piracetam displays a linear and time-dependent pharmacokinetic properties with low intersubject variability over a large range of doses. Piracetam is rapidly and extensively absorbed following oral administration with the peak plasma concentration is reached within 1 hour after dosing in fasted subjects. Following a single oral dose of 3.2 g piracetam, the peak plasma concentration (Cmax) was 84 g/mL. Intake of food may decrease the Cmax by 17% and increase the time to reach Cmax (Tmax) from 1 to 1.5 hours. Tmax in the cerebrospinal fluid is achieved approximately 5 hours post-administration. The absolute bioavailability of piracetam oral formulations is close to 100% and the steady state plasma concentrations are achieved within 3 days of dosing.


Route of Elimination

Piracetam is predominantly excreted via renal elimination, where about 80-100% of the total dose is recovered in the urine. Approximately 90% of the dose of piracetam is excreted in the urine as unchanged drug.


Volume of Distribution

Vd is approximately 0.6L/kg. Piracetam may cross the blood-brain barrier as it was measured in the cerebrospinal fluid following intravenous administration. Piracetam diffuses to all tissues except adipose tissues, crosses placental barrier and penetrates the membranes of isolated red blood cells.


Clearance

The apparent total body clearance is 80-90 mL/min.


Piracetam is rapidly and almost completely absorbed. Peak plasma levels are reached within 1.5 hours after administration. The extent of oral bioavailability, assessed from the Area Under Curve (AUC), is close to 100% for capsules, tablets and solution.

Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/


Peak levels and AUC are proportional to the dose given. The volume of distribution of piracetam is 0.7 L/kg, and ... Clearance of the compound is dependent on the renal creatinine clearance and would be expected to diminish with renal insufficiency.

Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/


Piracetam is excreted in human breast milk.

Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/


Piracetam crosses the blood-brain and the placental barrier and diffuses across membranes used in renal dialysis.

Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/


Piracetam is excreted almost completely in urine and the fraction of the dose excreted in urine is independent of the dose given.

Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/


5.5 Metabolism/Metabolites

As large proportion of total piracetam administered is excreted as unchanged drug, there is no known major metabolism of piracetam.


... No metabolite of piracetam has been found.

Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/


5.6 Biological Half-Life

The plasma half life of piracetam is approximately 5 hours following oral or intravenous administration. The half life in the cerebrospinal fluid was 8.5 hours.


... The plasma half-life is 5.0 hours, in young adult men.

Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/


5.7 Mechanism of Action

Piracetam interacts with the polar heads in the phospholipids membrane and the resulting mobile drug-lipid complexes are thought to reorganize the lipids and influence membrane function and fluidity. Such interaction has been reported in a study that investigated the effects of neuronal outgrowth induced by beta amyloid peptides; while amyloid peptides cause lipid disorganization within the cell membranes leading to neuronal death, piracetam demonstrated to decrease the destabilizing effects of amyloid peptide. The authors suggest that piracetam induces a positive curvature of the membrane by occupying the polar groups in the phospholipids to counteract the negative curvature induced by amyloid peptides , which in turn would decrease the likelihood of membrane fusion. This mechanism of action is thought to improve membrane stability, allowing the membrane and transmembrane proteins to maintain and recover the three-dimensional structure or folding for normal function such as membrane transport, chemical secretion, and receptor binding and stimulation. Through restored membrane fluidity, piracetam promotes restored neurotransmission such as glutamatergic and cholinergic systems, enhances neuroplasticity and mediates neuroprotective and anticonvulsant effects at the neuronal level. It is also demonstrated that piracetam also improves the fluidity of platelet membranes. At the vascular level, piracetam decreases adhesion of erythrocytes to cell wall and reduces vasospasm which in turn improves microcirculation including cerebral and renal blood flow.


It was found that a drug of the nootropic nature piracetam possessing pronounced antihypoxic properties eliminates calcium chloride-induced disturbances of the cardiac rhythm and significantly raises the threshold of atrial fibrillation during electrical stimulation. The drug's antiarrhythmic effect is followed by a decrease of the rhythm rate and an increase of the contraction amplitude. The animals treated with piracetam in a dose when its antiarrhythmic effects (300 mg/kg) exhibited a decrease of the membrane potential of erythrocytes as compared with control. Similar effects occurred in the animals treated with lidocaine. It can be concluded that in certain types of arrhythmias the use of piracetam restores the normal rhythm of contractions that is perhaps connected with its positive influence on metabolic processes in the myocardium.

PMID:2081561 Samvelian V et al; Farmakol Toksikol 53 (6): 22-3 (1990)


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