ContaminantDB: Methsuximide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:29:00 UTC

Update Date

2026-03-27 02:10:22 UTC

Accession Number

CHEM002411

Identification

Common Name

Methsuximide

Class

Small Molecule

Description

Methsuximide is only found in individuals that have used or taken this drug. It is an anticonvulsant medication. It is sold by Pfizer under the name Petinutin. [Wikipedia] Binds to T-type voltage sensitive calcium channels. Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1G gives rise to T-type calcium currents. T-type calcium channels belong to the low-voltage activated (LVA) group and are strongly blocked by mibefradil. A particularity of this type of channels is an opening at quite negative potentials and a voltage-dependent inactivation. T-type channels serve pacemaking functions in both central neurons and cardiac nodal cells and support calcium signaling in secretory cells and vascular smooth muscle. They may also be involved in the modulation of firing patterns of neurons which is important for information processing as well as in cell growth processes.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anticonvulsant
Drug
Metabolite
Organic Compound
Succinimide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Mesuximide	Kegg
Celontin	Kegg
(RS)-1,3-Dimethyl-3-phenyl-2,5-pyrrolidindion	HMDB
1,3-Dimethyl-3-phenyl-2,5-dioxopyrrolidine	HMDB
1,3-Dimethyl-3-phenyl-2,5-pyrrolidinedione	HMDB
1,3-Dimethyl-3-phenyl-pyrrolidin-2,5-dione	HMDB
1,3-Dimethyl-3-phenylsuccinimide	HMDB
alpha-Methyl-alpha-phenyl N-methyl succinimide	HMDB
alpha-Methylphensuximide	HMDB
Methsuximid	HMDB
Metosuccimmide	HMDB
Metsuccimide	HMDB
N,2-Dimethyl-2-phenylsuccinimide	HMDB
N-Methyl-alpha-methyl-alpha-phenylsuccinimide	HMDB
Pfizer brand OF methsuximide	HMDB
Methsuximide, (+)-isomer	HMDB
Warner-lambert brand OF methsuximide	HMDB
Mesuximid	HMDB
Parke david brand OF methsuximide	HMDB
Methsuximide, (-)-isomer	HMDB
Petinutin	HMDB
Methsuximide, (+-)-isomer	HMDB

Chemical Formula

C₁₂H₁₃NO₂

Average Molecular Mass

203.237 g/mol

Monoisotopic Mass

203.095 g/mol

CAS Registry Number

77-41-8

IUPAC Name

1,3-dimethyl-3-phenylpyrrolidine-2,5-dione

Traditional Name

methsuximide

SMILES

CN1C(=O)CC(C)(C1=O)C1=CC=CC=C1

InChI Identifier

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

InChI Key

AJXPJJZHWIXJCJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Phenylpyrrolidines

Direct Parent

Phenylpyrrolidines

Alternative Parents

Substituents

3-phenylpyrrolidine
Monocyclic benzene moiety
Carboxylic acid imide, n-substituted
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Benzenoid
Carboxylic acid imide
Dicarboximide
Pyrrole
Lactam
Carboxylic acid derivative
Azacycle
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	52.5°C
Boiling Point	121.5°C at 1.00E-01 mm Hg
Solubility	2.13e+00 g/L

Predicted Properties

Property	Value	Source
Water Solubility	2.13 g/L	ALOGPS
logP	1.46	ALOGPS
logP	1.46	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	19.03	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	37.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.35 m³·mol⁻¹	ChemAxon
Polarizability	21.4 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-3910000000-9cae394b5b94a483c401	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-0090000000-31b6e0b0429306f0d6da	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-0490000000-37eb2b7cfbb3d8b42e97	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-3910000000-9cae394b5b94a483c401	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-0090000000-31b6e0b0429306f0d6da	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-0490000000-37eb2b7cfbb3d8b42e97	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxr-0900000000-e0b7a163d2486262e40a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-0390000000-00d729cf9e85b7d75068	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-1690000000-0a263ad37a0831b81fb3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-4910000000-eb0a383017c0566e6a11	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014l-9800000000-5df2aae06682d9488eef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-05mo-9400000000-6de622fc3efce00a0b34	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-052f-9300000000-1e2faae8b516a3fc7ad5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-014i-4910000000-3edaee012b8d0ab6abab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0udi-0290000000-7e1ec4ffc809d1b17f69	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-1690000000-634173d911d8c9526bda	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-014l-9800000000-fe9ec2e272ddfa852102	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-05mo-9400000000-0014609b9f8d422ac9b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-052f-9200000000-4e2b70d601f365fae12e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-7bd86034fa816a0243c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0190000000-4ce7c75dd0aecca4396f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-9600000000-bf46c29670f52d82e8ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-e3773732d15693b117d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1190000000-d519c86bfcc321cacfa4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-6900000000-7c462fe20661937889fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-b81b75e675178531e9bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-1960000000-8ff948008064ff6c3bf3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-8900000000-b05d83746feabe3e2ce4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-341f1e0a28e483a04bd3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ufr-6920000000-366e7547f18799baaf74	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-675b081ad6d6943d7c75	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-4910000000-aa3742fc04cdbcda351f	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral

Mechanism of Toxicity

Methsuximide 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.

Metabolism

Half Life: 1.4-2.6 hours for mesuximide and 28-38 hours for the active metabolite.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the control of absence (petit mal) seizures that are refractory to other drugs.

Minimum Risk Level

Not Available

Health Effects

May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

Symptoms

Acute overdoses may produce nausea, vomiting, and CNS depression including coma with respiratory depression. Levels greater than 40 µg/mL have caused toxicity and coma has been seen at levels of 150 µg/mL.

Treatment

Treatment 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. (3)

Concentrations

Not Available

External Links

DrugBank ID

DB05246

HMDB ID

HMDB0015611

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID