| Revision as of 11:24, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{drugbox}} taken from revid 464291767 of page Oxiracetam for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 14:33, 12 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| verifiedrevid = 462241119 |
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| verifiedrevid = 464373213 |
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| IUPAC_name = (''RS'')-2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetamide |
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| IUPAC_name = (''RS'')-2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetamide |
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| image = Oxiracetam.svg |
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| image = Oxiracetam.svg |
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| image_class = skin-invert-image |
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| width = 120px |
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| width = 120px |
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| image2 = Oxiracetam3d.png |
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| image2 = Oxiracetam.png |
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| image_class2 = bg-transparent |
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| width2 = 120px |
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| width2 = 120px |
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| imagename = 1 : 1 mixture (racemate) |
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| chirality = ] |
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| drug_name = Oxiracetam |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_AU = S4 |
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| legal_status = Unscheduled (US) |
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| legal_US = Unscheduled |
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| routes_of_administration = Oral |
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| routes_of_administration = Oral |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = 56-82% |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = 8 hours |
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| excretion = |
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| excretion = Renal |
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| onset = 30-90 Minutes |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 62613-82-5 --> |
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| CAS_number = 62613-82-5 |
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| ATC_prefix = N06 |
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| ATC_prefix = N06 |
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| ATC_suffix = BX07 |
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| ATC_suffix = BX07 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=6 | H=10 | N=2 | O=3 |
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| C=6 | H=10 | N=2 | O=3 |
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| molecular_weight = 158.155 |
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| smiles = O=C(N)CN1C(=O)CC(O)C1 |
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| smiles = O=C(N)CN1C(=O)CC(O)C1 |
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| InChI = 1/C6H10N2O3/c7-5(10)3-8-2-4(9)1-6(8)11/h4,9H,1-3H2,(H2,7,10) |
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| InChIKey = IHLAQQPQKRMGSS-UHFFFAOYAL |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H10N2O3/c7-5(10)3-8-2-4(9)1-6(8)11/h4,9H,1-3H2,(H2,7,10) |
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| StdInChI = 1S/C6H10N2O3/c7-5(10)3-8-2-4(9)1-6(8)11/h4,9H,1-3H2,(H2,7,10) |
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| StdInChIKey = IHLAQQPQKRMGSS-UHFFFAOYSA-N |
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| StdInChIKey = IHLAQQPQKRMGSS-UHFFFAOYSA-N |
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}} |
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}} |
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'''Oxiracetam''' (developmental code name '''ISF 2522''') is a ] drug of the ] family and a very mild ].<ref>{{cite journal | vauthors = Malykh AG, Sadaie MR | title = Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders | journal = Drugs | volume = 70 | issue = 3 | pages = 287–312 | date = February 2010 | pmid = 20166767 | doi = 10.2165/11319230-000000000-00000 | s2cid = 12176745 }}</ref><ref>{{cite journal | vauthors = Valzelli L, Baiguerra G, Giraud O | title = Difference in learning and retention by Albino Swiss mice. Part III. Effect of some brain stimulants | journal = Methods and Findings in Experimental and Clinical Pharmacology | volume = 8 | issue = 6 | pages = 337–41 | date = June 1986 | pmid = 3736279 }}</ref> Several studies suggest that the substance is safe even when high doses are consumed for a long period of time.<ref>{{cite journal | vauthors = Parnetti L, Mecocci P, Petrini A, Longo A, Buccolieri A, Senin U | title = Neuropsychological results of long-term therapy with oxiracetam in patients with dementia of Alzheimer type and multi-infarct dementia in comparison with a control group | journal = Neuropsychobiology | volume = 22 | issue = 2 | pages = 97–100 | year = 1989 | pmid = 2518332 | doi = 10.1159/000118599 }}</ref><ref>{{cite journal | vauthors = Itil TM, Menon GN, Songar A, Itil KZ | title = CNS pharmacology and clinical therapeutic effects of oxiracetam | journal = Clinical Neuropharmacology | volume = 9 | pages = S70-2 | year = 1986 | issue = Suppl 3 | pmid = 3594458 | doi = 10.1097/00002826-198609003-00011 }}</ref><ref>{{cite journal | vauthors = Perucca E, Parini J, Albrici A, Visconti M, Ferrero E | title = Oxiracetam pharmacokinetics following single and multiple dose administration in the elderly | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 12 | issue = 2 | pages = 145–8 | year = 1987 | pmid = 3691580 | doi = 10.1007/bf03189889 | s2cid = 11415210 }}</ref> However, the ] of the ] drug family is still a matter of research. Oxiracetam is not approved by ] for any medical use in the United States. |
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==Clinical findings== |
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Oxiracetam has been studied to determine if it has an effect on symptoms of dementia,<ref name="Gouliaev">{{cite journal | vauthors = Gouliaev AH, Senning A | title = Piracetam and other structurally related nootropics | journal = Brain Research. Brain Research Reviews | volume = 19 | issue = 2 | pages = 180–222 | date = May 1994 | pmid = 8061686 | doi = 10.1016/0165-0173(94)90011-6 | s2cid = 18122566 }}</ref> but no consistent results were obtained in patients with ] or organic solvent abuse.<ref name="Gouliaev"/> |
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Patients with mild to moderate ] experienced some beneficial effects, measured by higher scores on tests for logical performance, attention, concentration, memory and spatial orientation. Improvement was also seen in patients with exogenic post-concussion syndrome, organic brain syndromes and other dementias.<ref name="Gouliaev"/> |
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Oxiracetam-treated ] demonstrated a significant increase in spatial learning performance as determined by the ], compared to controls. This increase in performance was correlated to an increase in membrane-bound PKC.<ref>{{cite journal | vauthors = Fordyce DE, Clark VJ, Paylor R, Wehner JM | title = Enhancement of hippocampally-mediated learning and protein kinase C activity by oxiracetam in learning-impaired DBA/2 mice | journal = Brain Research | volume = 672 | issue = 1–2 | pages = 170–6 | date = February 1995 | pmid = 7749739 | doi = 10.1016/0006-8993(94)01389-y | s2cid = 13191058 }}</ref> |
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==Pharmacokinetics== |
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Oxiracetam is well absorbed from the gastrointestinal tract with a bioavailability of 56-82%.<ref name="Gouliaev"/> |
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Peak serum levels are reached within one to three hours after a single 800 mg or 2000 mg oral dose, with the maximal serum concentration reaching between 19 and 31 μg/ml at these doses. |
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Oxiracetam is mainly cleared renally and approximately 84% is excreted unchanged in the urine. |
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The half-life of oxiracetam in healthy individuals is about 8 hours, whereas it is 10–68 hours in patients with renal impairment. |
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There is some penetration of the ] with brain concentrations reaching 5.3% of those in the blood (measured one hour after a single 2000 mg intravenous dose).<ref name="Gouliaev"/> |
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Clearance rates range from 9 to 95 ml/min and steady-state concentrations when 800 mg is given twice daily range from 60 μM to 530 μM. |
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The highest brain concentrations of oxiracetam are found in the ], followed by the ], the ] and with the lowest concentrations in the striatum after a 200 mg/kg oral dose given to rats.<ref name="Gouliaev"/> Oxiracetam may be quantitated in plasma, serum or urine by liquid chromatography with one of several different detection techniques.<ref>{{cite book | vauthors = Baselt R | title = Disposition of Toxic Drugs and Chemicals in Man | edition = 10th | publisher = Biomedical Publications | location = Seal Beach, CA | date = 2014 | pages = 1524–1525 }}</ref> |
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The major metabolites of Oxiracetam include: beta-hydroxy-], N-aminoacetyl-], GABOB (beta-hydroxy-GABA) and ].{{Citation needed|date=May 2018}} Thus its metabolic route is exactly parallel to that of ], ], ], and all other members of the -racetam family, and also ]. |
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== References == |
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{{Reflist}} |
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== External links == |
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* |
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== Further reading == |
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{{refbegin}} |
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* {{cite journal | vauthors = Bottini G, Vallar G, Cappa S, Monza GC, Scarpini E, Baron P, Cheldi A, Scarlato G | title = Oxiracetam in dementia: a double-blind, placebo-controlled study | journal = Acta Neurologica Scandinavica | volume = 86 | issue = 3 | pages = 237–41 | date = September 1992 | pmid = 1414239 | doi = 10.1111/j.1600-0404.1992.tb05077.x | s2cid = 9368980 | doi-access = free }} |
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* {{cite journal |last1=Li|first1=W |title=(S)-Oxiracetam is the Active Ingredient in Oxiracetam that Alleviates the Cognitive Impairment Induced by Chronic Cerebral Hypoperfusion in Rats |journal=Sci. Rep. |date=2017 |volume=7 |issue=1 |page=10052 |doi=10.1038/s41598-017-10283-4 |pmid=28855592 |pmc=5577264 |bibcode=2017NatSR...710052L |doi-access=free }} |
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* {{cite journal |last1=Villardita |first1=C|title=Clinical Studies with Oxiracetam in Patients with Dementia of Alzheimer Type and Multi-lnfarct Dementia of Mild to Moderate Degree |journal=Neuropsychobiology |date=1992 |volume=25 |issue=1|pages=24–28 |doi=10.1159/000118805 |pmid=1603291 }} |
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* {{cite journal |last1=Mondadori |first1=C |title=Effects of oxiracetam on learning and memory in animals: comparison with piracetam |journal=Clin. Neuropharmacol. |date=1986 |volume=9 |issue=Supp.3 |pages=S27-38 |doi=10.1097/00002826-198609003-00006 |pmid=3594453 |url=https://pubmed.ncbi.nlm.nih.gov/3594453/}} |
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* {{cite journal |last1=Hu |first1=S |title=Oxiracetam or fastigial nucleus stimulation reduces cognitive injury at high altitude |journal=Brain and Behavior |date=2017 |volume=7 |issue=10 |pages=e00762 |doi=10.1002/brb3.762|pmid=29075554 |pmc=5651378 |doi-access=free }} |
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* {{cite journal |last1=Krylova |first1=N |title=A comparative study of the nootropic properties of piracetam and oxiracetam |journal=Farmakologiia I Toksikologiia |date=1991 |volume=54 |issue=1 |pages=14–6 |pmid=1860490 }} |
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{{refend}} |
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{{Racetams}} |
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{{Stimulants}} |
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{{Ionotropic glutamate receptor modulators}} |
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] |
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] |
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] |
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] |
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] |
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] |