Mesuximide: Difference between revisions

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{{Drugbox|
{{Drugbox
|IUPAC_name = 1,3-dimethyl-3-phenyl-pyrrolidine-2,5-dione
| Verifiedfields = changed
| image= Mesuximide.svg
| verifiedrevid = 411374493
| CAS_number=77-41-8
| IUPAC_name = (''RS'')-1,3-dimethyl-3-phenyl-pyrrolidine-2,5-dione
| ATC_prefix=N03
| image = Mesuximide.svg
| ATC_suffix=AD03
| width = 250px
| PubChem=6476
| imagename = 1 : 1 mixture (racemate)
| DrugBank=
| drug_name = Mesuximide
| C = 12 | H = 13 | N = 1 | O = 2
 
| molecular_weight = 203.237 g/mol
<!--Clinical data-->
| bioavailability=
| tradename =
| metabolism = [[Liver|Hepatic]] ([[demethylation]] and [[glucuronidation]])
| Drugs.com = {{drugs.com|CDI|methsuximide}}
| elimination_half-life=1.4–2.6 hours <small>(mesuximide)</small><br>28–38 hours <small>(active metabolite)</small>
| MedlinePlus = a682028
| excretion = [[Kidney|Renal]]
| pregnancy_US = C
| pregnancy_US = C
| legal_US = Rx-only
| legal_US = Rx-only
| routes_of_administration = Oral
| routes_of_administration = Oral
<!--Pharmacokinetic data-->
| metabolism = [[Liver|Hepatic]] ([[demethylation]] and [[glucuronidation]])
| elimination_half-life = 1.4–2.6 hours <small>(mesuximide)</small><br>28–38 hours <small>(active metabolite)</small>
| excretion = [[Kidney|Renal]]
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 77-41-8
| ATC_prefix = N03
| ATC_suffix = AD03
| PubChem = 6476
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB05246
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6231
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0G76K8X6C0
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00404
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 697
<!--Chemical data-->
| C=12 | H=13 | N=1 | O=2
| molecular_weight = 203.237 g/mol
| smiles = O=C2N(C(=O)CC2(c1ccccc1)C)C
| InChI = 1/C12H13NO2/c1-12(9-6-4-3-5-7-9)8-10(14)13(2)11(12)15/h3-7H,8H2,1-2H3
| InChIKey = AJXPJJZHWIXJCJ-UHFFFAOYAR
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H13NO2/c1-12(9-6-4-3-5-7-9)8-10(14)13(2)11(12)15/h3-7H,8H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AJXPJJZHWIXJCJ-UHFFFAOYSA-N
}}
}}
'''Mesuximide''' (or '''methsuximide''') is an [[anticonvulsant]] medication. It is sold by [[Pfizer]] under the name '''Petinutin®'''.<ref name=Petinutin>{{cite web | author = Pfizer AG | year = 2005 | url = http://www.pfizer.ch/internet/fr/home/products/central_nervous_system/epilepsy/petinutin_mesuximid.html | title = Petinutin® (Mésuximide) | work = Official Pfizer AG Website | accessmonthday = August 21 | accessyear = 2006 | language = French }}</ref>
 
'''Mesuximide''' (or '''methsuximide''', '''methosuximide''') is a [[succinimide]] [[anticonvulsant]] medication. It is sold as a [[racemate]] by [[Pfizer]] under the tradenames '''Petinutin''' (Switzerland)<ref name=Petinutin>{{cite web | author = Pfizer AG | year = 2005 | url = http://www.pfizer.ch/internet/fr/home/products/central_nervous_system/epilepsy/petinutin_mesuximid.html | title = Petinutin (Mésuximide) | work = Official Pfizer AG Website | accessdate = August 21, 2006 | language = French }} {{Dead link|date=November 2010|bot=H3llBot}}</ref> and '''Celontin''' (United States).<ref name=Celontin>{{cite web | author = Pfizer Inc. | year = 2008 | url = http://labeling.pfizer.com/ShowLabeling.aspx?id=555 | title = Celontin (methsuximide capsules, USP) | work = Official Pfizer Inc. Website | accessdate = November 21, 2014 | language = }}</ref> The therapeutic efficacy of methosuximide is largely due to its pharmacologically active metabolite, N-desmethylmethosuximide, which has a longer half-life and attains much higher plasma levels than its parent.<ref>Porter RJ, Penry JK, Lacy JR, Newmark ME, Kupferberg HJ. Plasma concentrations of phensuximide, methosuximide, and their metabolites in relation to clinical efficacy. Neurology 29: 1509-1513, 1979.</ref>


==References==
==References==
<div class="references-small"><references/></div>
{{Reflist}}


{{Anticonvulsants}}
{{Anticonvulsants}}


[[Category:Anticonvulsants]]
[[Category:Anticonvulsants]]
[[Category:Succinimides]]
{{anticonvulsant-stub}}
{{anticonvulsant-stub}}
[[de:Mesuximid]]
{{WikiDoc Sources}}

Revision as of 18:43, 9 April 2015

Mesuximide
File:Mesuximide.svg
Clinical data
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa682028
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismHepatic (demethylation and glucuronidation)
Elimination half-life1.4–2.6 hours (mesuximide)
28–38 hours (active metabolite)
ExcretionRenal
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC12H13NO2
Molar mass203.237 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Mesuximide (or methsuximide, methosuximide) is a succinimide anticonvulsant medication. It is sold as a racemate by Pfizer under the tradenames Petinutin (Switzerland)[1] and Celontin (United States).[2] The therapeutic efficacy of methosuximide is largely due to its pharmacologically active metabolite, N-desmethylmethosuximide, which has a longer half-life and attains much higher plasma levels than its parent.[3]

References

  1. ↑ Pfizer AG (2005). "Petinutin (Mésuximide)". Official Pfizer AG Website (in French). Retrieved August 21, 2006.[dead link]
  2. ↑ Pfizer Inc. (2008). "Celontin (methsuximide capsules, USP)". Official Pfizer Inc. Website. Retrieved November 21, 2014.
  3. ↑ Porter RJ, Penry JK, Lacy JR, Newmark ME, Kupferberg HJ. Plasma concentrations of phensuximide, methosuximide, and their metabolites in relation to clinical efficacy. Neurology 29: 1509-1513, 1979.

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