Mesuximide

Mesuximide

Systematic (IUPAC) name
(RS)-1,3-dimethyl-3-phenyl-pyrrolidine-2,5-dione
Clinical data
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a682028
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Oral
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Metabolism	Hepatic (demethylation and glucuronidation)
Biological half-life	1.4–2.6 hours (mesuximide) 28–38 hours (active metabolite)
Excretion	Renal
Identifiers
CAS Number	77-41-8
ATC code	N03AD03 (WHO)
PubChem	CID 6476
IUPHAR/BPS	7228
DrugBank	DB05246
ChemSpider	6231
UNII	0G76K8X6C0
KEGG	D00404
ChEMBL	CHEMBL697
Chemical data
Formula	C12H13NO2
Molar mass	203.237 g/mol
Chirality	Racemic mixture
SMILES O=C2N(C(=O)CC2(c1ccccc1)C)C
InChI InChI=1S/C12H13NO2/c1-12(9-6-4-3-5-7-9)8-10(14)13(2)11(12)15/h3-7H,8H2,1-2H3 Key:AJXPJJZHWIXJCJ-UHFFFAOYSA-N
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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). Archived from the original on April 22, 2005. Retrieved August 21, 2006.
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.