Mesuximide - Misplaced Pages

Chemical compound Pharmaceutical compound

Mesuximide
Clinical data

Trade names	Celontin
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a682028
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
Elimination 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
PubChem CID	6476
IUPHAR/BPS	7228
DrugBank	DB05246
ChemSpider	6231
UNII	0G76K8X6C0
KEGG	D00404
ChEMBL	ChEMBL697
CompTox Dashboard (EPA)	DTXSID5023293
ECHA InfoCard	100.000.934
Chemical and physical data
Formula	C₁₂H₁₃NO₂
Molar mass	203.241 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 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) and Celontin (United States). 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.

Medical use

is indicated for the control of absence seizures that are refractory to other drugs.

References

Pfizer AG (2005). "Petinutin (Mésuximide)". Official Pfizer AG Website (in French). Archived from the original on April 22, 2005. Retrieved August 21, 2006.
^ 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 (November 1979). "Plasma concentrations of phensuximide, methsuximide, and their metabolites in relation to clinical efficacy". Neurology. 29 (11): 1509–13. doi:10.1212/wnl.29.11.1509. PMID 116142. S2CID 43643797.

Anticonvulsants (N03)

GABAergics

GABA_AR PAMs	Barbiturates: Barbexaclone Metharbital Methylphenobarbital Pentobarbital Phenobarbital Primidone; Carbamates: Cenobamate Felbamate; Benzodiazepines: Clobazam Clonazepam Clorazepate Diazepam Lorazepam Midazolam Nimetazepam Nitrazepam Temazepam; Others: Bromide (potassium bromide, sodium bromide) Imepitoin Paraldehyde Stiripentol
GABA-T inhibitors	Fatty acids (and related): Valproate Valpromide Valproate pivoxil 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: Imepitoin Lamotrigine Topiramate Zonisamide
Potassium openers	Retigabine

Others

CA inhibitors	Sulfonamides: Acetazolamide Ethoxzolamide Sultiame Topiramate Zonisamide
Others	Albutoin Beclamide Brivaracetam Cannabidiol Carisbamate Etiracetam Fenfluramine Ganaxolone Levetiracetam Perampanel

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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