Mesuximide

Mesuximide
Clinical data

Trade names	Celontin
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a682028
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	By mouth (capsules)
ATC code	N03AD03 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Metabolism	Hepatic (demethylation and glucuronidation)
Metabolites	N-desmethylmethosuximide
Biological half-life	1.4–2.6 hours (mesuximide) 28–38 hours (active metabolite)
Excretion	Urine
Identifiers
IUPAC name (RS)-1,3-dimethyl-3-phenyl-pyrrolidine-2,5-dione
CAS Number	77-41-8^Y
PubChem CID	6476
IUPHAR/BPS	7228
DrugBank	DB05246^N
ChemSpider	6231^Y
UNII	0G76K8X6C0
KEGG	D00404^Y
ChEMBL	CHEMBL697^Y
ECHA InfoCard	100.000.934
Chemical and physical data
Formula	C₁₂H₁₃NO₂
Molar mass	203.237 g/mol
3D model (JSmol)	Interactive image
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^Y Key:AJXPJJZHWIXJCJ-UHFFFAOYSA-N^Y
^NY (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]

Medical use

is indicated for the control of absence seizures that are refractory to other drugs.^[2]

References

↑ Pfizer AG (2005). "Petinutin (Mésuximide)". Official Pfizer AG Website (in French). Archived from the original on April 22, 2005. Retrieved August 21, 2006.
1 2 Pfizer Inc. (2008). "Celontin (methsuximide capsules, USP)". Official Pfizer Inc. Website. Retrieved November 21, 2014.
↑ 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.

Anticonvulsants (N03)

GABAergics

GABA_AR PAMs	Barbiturates: Barbexaclone Metharbital Methylphenobarbital Pentobarbital Phenobarbital^# Primidone; Carbamates: Felbamate; Benzodiazepines: Clobazam Clonazepam Clorazepate Diazepam^# Lorazepam^# Midazolam Nimetazepam Nitrazepam Temazepam; Others: Bromide (potassium bromide, sodium bromide) Paraldehyde Stiripentol
GABA-T inhibitors	Fatty acids: Valproate Valpromide Valproate pivoxil; Others: Ethanolamine-O-sulfate Vigabatrin
Others	GABAR agonists: Progabide; GAT-1 inhibitors: Tiagabine

Channel
modulators

Sodium blockers	Hydantoins: Ethotoin Fosphenytoin Mephenytoin Phenytoin^#; Ureides: Acetylpheneturide Chlorphenacemide Phenacemide^‡ Pheneturide; Fatty acids: Valproate Valpromide Valproate pivoxil; Carboxamides: Carbamazepine^# Eslicarbazepine acetate Oxcarbazepine; Others: Lacosamide Lamotrigine Rufinamide Topiramate Zonisamide
Calcium blockers	Oxazolidinediones: Ethadione Paramethadione Trimethadione; Succinimides: Ethosuximide^# Mesuximide Phensuximide; Gabapentinoids: Gabapentin Pregabalin; Others: Lamotrigine Topiramate Zonisamide
Potassium openers	Retigabine

Others

CA inhibitors	Sulfonamides: Acetazolamide Ethoxzolamide Sultiame Topiramate Zonisamide
Others	Albutoin Beclamide Brivaracetam Levetiracetam Perampanel

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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