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Mesuximide: Difference between revisions

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{{short description|Chemical compound}}
⚫ {{Drugbox| verifiedrevid = 402387017
{{Drugbox
| drug_name = Mesuximide
| Verifiedfields = changed
⚫ |IUPAC_name = (''RS'')-1,3-dimethyl-3-phenyl-pyrrolidine-2,5-dione
⚫ | verifiedrevid = 411374493
| image= Mesuximide.svg
⚫ | IUPAC_name = (''RS'')-1,3-dimethyl-3-phenyl-pyrrolidine-2,5-dione
| imagename = 1 : 1 mixture (racemate)
| width = 250px | image = Mesuximide.svg
| image_class = skin-invert-image
| width = 150
| chirality = ]

<!--Clinical data-->
| tradename = Celontin
| Drugs.com = {{drugs.com|CDI|methsuximide}}
| MedlinePlus = a682028
⚫ | pregnancy_US = C
⚫ | legal_US = Rx-only
| routes_of_administration = ] (])

<!--Pharmacokinetic data-->
⚫ | metabolism = ] (] and ])
| metabolites = ''N''-desmethylmethosuximide
⚫ | elimination_half-life = 1.4–2.6 hours <small>(mesuximide)</small><br>28–38 hours <small>(active metabolite)</small>
⚫ | excretion = ]

<!--Identifiers-->
| IUPHAR_ligand = 7228
⚫ | 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_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6231 | ChemSpiderID = 6231
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 697
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0G76K8X6C0 | UNII = 0G76K8X6C0
| KEGG_Ref = {{keggcite|correct|kegg}}
| 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
⚫ | KEGG = D00404
| InChIKey = AJXPJJZHWIXJCJ-UHFFFAOYAR
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 697

<!--Chemical data-->
⚫ | C=12 | H=13 | N=1 | O=2
| smiles = O=C2N(C(=O)CC2(c1ccccc1)C)C | smiles = O=C2N(C(=O)CC2(c1ccccc1)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AJXPJJZHWIXJCJ-UHFFFAOYSA-N | StdInChIKey = AJXPJJZHWIXJCJ-UHFFFAOYSA-N
⚫ | CAS_number=77-41-8
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | ATC_prefix=N03
⚫ | ATC_suffix=AD03
⚫ | PubChem=6476
⚫ | DrugBank=
⚫ | KEGG = D00404
⚫ | C = 12 | H = 13 | N = 1 | O = 2
| molecular_weight = 203.237 g/mol
| bioavailability=
⚫ | metabolism = ] (] and ])
⚫ | elimination_half-life=1.4–2.6 hours <small>(mesuximide)</small><br>28–38 hours <small>(active metabolite)</small>
⚫ | excretion = ]
⚫ | pregnancy_US = C
⚫ | legal_US = Rx-only
| routes_of_administration = Oral
}} }}


'''Mesuximide''' (or '''methsuximide''') is an ] ] medication. It is sold as a ] by ] 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://www.pfizer.com/products/rx/rx_product_celontin.jsp | title = Celontin (methsuximide capsules, USP) | work = Official Pfizer Inc. Website | accessdate = June 10, 2008 | language = }}</ref> The therapeutic efficacy of methsuximide is largely due to its pharmacologically active metabolite, N-desmethylmethsuximide, 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. '''Mesuximide''' (or '''methsuximide''', '''methosuximide''') is a ] ] medication. It is sold as a ] by ] 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 |access-date=August 21, 2006 |language=fr |url-status=dead |archive-url=https://web.archive.org/web/20050422010830/http://www.pfizer.ch/internet/fr/home/products/central_nervous_system/epilepsy/petinutin_mesuximid.html |archive-date=April 22, 2005 }}</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 | access-date = November 21, 2014 }}</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 name="pmid116142">{{cite journal | vauthors = Porter RJ, Penry JK, Lacy JR, Newmark ME, Kupferberg HJ | title = Plasma concentrations of phensuximide, methsuximide, and their metabolites in relation to clinical efficacy | journal = Neurology | volume = 29 | issue = 11 | pages = 1509–13 | date = November 1979 | pmid = 116142 | doi = 10.1212/wnl.29.11.1509 | s2cid = 43643797 }}</ref>

Plasma concentrations of phensuximide, methsuximide, and their metabolites in relation to clinical efficacy.
==Medical use==
Neurology 29: 1509-1513, 1979.</ref>
is indicated for the control of ]s that are refractory to other drugs.<ref name=Celontin />


==References== ==References==
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