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HCID 6476Erstellt: 3. November 2026

Mesuximid

Celontin · PM 396 · Petinutin · Mesuximide · Mesuximidum · Methsuximid · Metsuccimide · METHSUXIMIDE

https://huagongshe.com/de/chemical/6476

Molekülstruktur von Mesuximid

Identifikatoren & physikalische Daten

CAS No.77-41-8
SummenformelC12H13NO2
Durchschnittliche Molmasse203,24 g/mol
Monoisotopische Masse203,09462866 g/mol
SMILESCN1C(=O)CC(C)(c2ccccc2)C1=O
InChIKeyAJXPJJZHWIXJCJ-UHFFFAOYSA-N
PubChem CID6476
ChEMBLCHEMBL697
ChEBICHEBI:6846
EC No.201-026-7
DTXSIDDTXSID5023293
Lokaler NameMesuximid

Chemische & physikalische Eigenschaften

XLogP1,2
Polarare Oberfläche (TPSA)37,4
H-Brücken-Donoren0
H-Brücken-Akzeptoren2
Frei drehbare Bindungen1
Schwere Atome15
Formalladung0
Komplexität294
ArzneimittelPharmaceuticalsPharmaceuticals -> Antiepileptics
GeruchOdorless to slight odor
Color/FormCrystals from dilute alcoholWhite to grayish white, crystalline powder
LöslichkeitFreely sol in methanol, alcoholSlightly soluble in hot waterfreely soluble in alcohol and ethervery soluble in chloroform.2.13e+00 g/LChloroform (Slightly), Methanol (Slightly)2.8g/L(25 ºC)
Human DrugsFDA approved drugs -> Active ingredient
Siedepunkt121-122 °C at 0.1 mm Hgbp0.1 121-122°
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/ .
Schmelzpunkt52-53 °C52.5 °C52-53°
Physical DescriptionSolid
Stability/Shelf LifeMethsuximide has a relatively low melting range (50 to 56 °C or 122 to 133 °F). Improper storage may result in melting and subsequent impaired absorption of the capsule contents. /Methsuximide Capsules USP/
Dichte1.1255 (rough estimate)
Brechungsindex1.5440 (estimate)
LagerbedingungenRefrigerator
AggregatzustandSolid
FarbeWhite to Off-White

Sicherheit & Vorschriften

GHS-EinstufungWarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische Informationen2,5-Pyrrolidinedione, 1,3-dimethyl-3-phenyl-: Does not have an individual approval but may be used under an appropriate group standard
Weitere SicherheitsinformationenIMAP assessments - 2,5-Pyrrolidinedione, 1,3-dimethyl-3-phenyl-: Environment tier I assessment
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl methsuximide, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Special ReportsSchardein JLChemically Induced Birth Defects 2: 157-207 (1993). Anticonvulsant induced birth defects.Gilstrap LC, Little BBDrugs and Pregnancy 125-32 (1992). Anticonvulsant drugs during pregnancy.Battino D, et alClin Pharmacokinet 29: 257-86 (1995). An overview of the clinical pharmacokinetics of ... methsuximide ... in pediatric patients is considered.Briggs GG, et alDrugs Preg Lactation 203-63 (1984). Drugs in pregnancy and lactation: A reference guide to fetal and neonatal risk.
Hazard Classes and CategoriesAcute Tox. 4 (100%)
LagerbedingungenStore below 30 °C (86 °F), preferably between 15 and 30 °C (59 and 86 °F), unless otherwise specified by manufacturer. Store in a tight container. Avoid exposure to excessive heat. /Methsuximide Capsules USP/
EntsorgungsverfahrenSRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Anwendungen & Verwendung

Beschreibung

Methsuximide is a succinimide that is converted to N-desmethylmethosuximide, a channel blocker that targets low threshold calcium currents. Methsuximide is a substrate of cytochrome P450 (CYP) isoform 2C19 that, in turn, inhibits CYP2C19-mediated metabolism of biguanides. Methsuximide has been shown to have anticonvulsant properties in clinical trials.

Verwenden

A calcium channel succinimide antiepileptic drug. Anticonvulsant.

TreatmentTreatment should include emesis (unless the patient is or could rapidly become obtunded, comatose, or convulsing) or gastric lavage, activated charcoal, cathartics, and general supportive measures. Charcoal hemoperfusion may be useful in removing the N-desmethyl metabolite of methsuximide. Forced diuresis and exchange transfusions are ineffective. (L1712)
WechselwirkungenConcurrent use /with alcoholcentral nervous system depression-producing medicationstricyclic antidepressantsloxapinemaprotilinemolindonemonoamine oxidase inhibitorsphenothiazinespimozidethioxanthenes/ may lower the convulsive threshold, enhance CNS depression, and decrease the effects of the anticonvulsant medication. /Succinimide anticonvulsants/Requirements for folic acid may be increased in patients receiving anticonvulsant therapy. /Succinimide anticonvulsants/Induction of hepatic microsomal enzyme activity resulting in increased metabolism and decreased serum concentrations and elimination half-lives of succinimide anticonvulsants and/or these medications /carbamazepine, phenobarbital, phenytoin, primidone/ may occur during concurrent therapymonitoring of serum concentrations as a guide to dosage is recommended, especially when any anticonvulsant is added to or withdrawn from an existing regimen. /Succinimide anticonvulsants/Concurrent use /with haloperidol/ may cause a change in the pattern and/or the frequency of epileptiform seizuresdosage adjustments of the anticonvulsant may be necessaryserum concentrations of haloperidol may be significantly reduced. /Succinimide anticonvulsants/For more Interactions (Complete) data for METHSUXIMIDE (9 total), please visit the HSDB record page.
Gesundheitliche AuswirkungenMay cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.
HepatotoxicityProspective studies suggest that chronic methsuximide therapy is not accompanied by significant elevations in serum aminotransferase levels, although it has been shown to have hepatotoxicity in animals. Clinically apparent hepatotoxicity from methsuximide has not been reported, although hypersensitivity reactions with fever and rash are not uncommon (1% to 5%). The product label for methsuximide warns of hepatic dysfunction and recommends periodic liver function studies. Nevertheless, clinically apparent liver injury from methsuximide must be very rare, if it occurs at all.
ExpositionspfadeOral
ToxizitätsübersichtMethsuximide suppresses the paroxysmal three cycle per second spike and wave activity associated with lapses of consciousness which is common in absence (petit mal) seizures. The frequency of epileptiform attacks is reduced, apparently by depression of the motor cortex and elevation of the threshold of the central nervous system to convulsive stimuli.
Signs and SymptomsAcute overdoses may produce nausea, vomiting, and CNS depression including coma with respiratory depression. Levels greater than 40 &#181g/mL have caused toxicity and coma has been seen at levels of 150 &#181g/mL.
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Adverse hematologic effects associated with methsuximide include eosinophilia, leukopenia, monocytosis, and pancytopenia. Adverse dermatologic effects may include urticaria, pruritic erythematous rash, and Steven-Johnson syndrome. Adverse genitourinary effects associated with methsuximide include proteinuria and microscopic hematuria. Periorbital edema and hyperemia have also occurred. Systemic lupus erythematosus has been associated with succinimide use./SIGNS AND SYMPTOMS/ GI disturbances such as ... diarrhea, wt loss, epigastric & abdominal pain, & constipation occur frequently. Hemopoietic complications including eosinophilia ... Monocytosis, & pancytopenia have been reported. Neurologic & sensory reactions observed including ... irritability, nervousness ... blurred vision, photophobia...and insomnia./SIGNS AND SYMPTOMS/ Dermatologic disturbances including urticaria, Stevens-Johnson syndrome, & pruritic erythematous rashes./SIGNS AND SYMPTOMS/ Drowsiness, gastrointestinal disturbance, hiccups, irritability, and headache /are/ the common side effects of methsuximide.For more Human Toxicity Excerpts (Complete) data for METHSUXIMIDE (9 total), please visit the HSDB record page.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver InjuryDrug Induced Liver Injury Rank (DILIrank 2.0)MethsuximidevNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ Phensuximide (PSX), methsuximide (MSX) and ethosuximide (ESX) are succinimide antiepileptie agents used worldwide in the treatment of absence seizures. A previous study ... demonstrated that PSX (0.3 or 0.6 mmol/kg/day ip) induced urotoxicity following daily administration for 5-7 days in Fischer 344 rats, but PSX (1.25 mmol/kg, ip) induced only minimal urotoxicity following acute administration. The purpose of this study was to determine the acute nephrotoxic potential of MSX and ESX in male Fischer 344 rats and if antiepileptic succinimide induced urotoxicity is potentiated by phenobarbital pretreatment. In one set of experiments, rats (four rats per group) were administered a single ip injection of a succinimide (0.4 or 1.0 mmol/kg) or vehicle (sesame oil, 2.5 mL/kg), and the renal function was monitored at 24 and 48 hr. Neither ESX or MSX induced substantial changes in renal function or morphology, which suggests that neither compound is acutely nephrotoxic. Similar results were obtained with PSX, whiCh supported ... earlier findings with this antiepileptic agent. In a second set of experiments, rats (four rats per group) were pretreated for 3 days with phenobarbital (75 mg kg/day, ip) prior to receiving a succinimide (0.4 or 1.0 mmol/kg, ip) or vehicle (sesame oil, 2.5 mL/kg, ip). Renal function was monitored at 24 and 48 hr after the last injection. Phenobarbital pretreatment had only minor effects on ESX or MSX induced renal effects, with no significant morphological changes detected between treated and pair fed control groups./LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... Drugs of widely differing pharmacological activity have been administered to partially hepatectomized male rats and the extent of liver regeneration ascertained over a period of ten days. ... The following fed ad lib in diets supplemented in a basal ration at the weight percent 0.15 methsuximide ... was hepatotrophic. ...
Environmental Water ConcentrationsWhile data specific to methsuximide were not located(SRC, 2007), the literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2).
Zollcode2925190100
ToxizitätLD50 orally in mice: 0.9 g/kg (Marshall, Vallance)
Gefahrstoffdaten77-41-8(Hazardous Substances Data)