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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:03 UTC
HMDB IDHMDB0015611
Secondary Accession Numbers
  • HMDB15611
Metabolite Identification
Common NameMethsuximide
DescriptionMethsuximide 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.
Structure
Data?1582753316
Synonyms
ValueSource
MesuximideKegg
CelontinKegg
(RS)-1,3-Dimethyl-3-phenyl-2,5-pyrrolidindionHMDB
1,3-Dimethyl-3-phenyl-2,5-dioxopyrrolidineHMDB
1,3-Dimethyl-3-phenyl-2,5-pyrrolidinedioneHMDB
1,3-Dimethyl-3-phenyl-pyrrolidin-2,5-dioneHMDB
1,3-Dimethyl-3-phenylsuccinimideHMDB
alpha-Methyl-alpha-phenyl N-methyl succinimideHMDB
alpha-MethylphensuximideHMDB
MethsuximidHMDB
MetosuccimmideHMDB
MetsuccimideHMDB
N,2-Dimethyl-2-phenylsuccinimideHMDB
N-Methyl-alpha-methyl-alpha-phenylsuccinimideHMDB
Pfizer brand OF methsuximideHMDB
Methsuximide, (+)-isomerHMDB
Warner-lambert brand OF methsuximideHMDB
MesuximidHMDB
Parke david brand OF methsuximideHMDB
Methsuximide, (-)-isomerHMDB
PetinutinHMDB
Methsuximide, (+-)-isomerHMDB
Chemical FormulaC12H13NO2
Average Molecular Weight203.2371
Monoisotopic Molecular Weight203.094628665
IUPAC Name1,3-dimethyl-3-phenylpyrrolidine-2,5-dione
Traditional Namemethsuximide
CAS Registry Number77-41-8
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 KeyAJXPJJZHWIXJCJ-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPhenylpyrrolidines
Direct ParentPhenylpyrrolidines
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 FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point52.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.13 g/LNot Available
LogP3.120 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.13 g/LALOGPS
logP1.46ALOGPS
logP1.46ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)19.03ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area37.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.35 m³·mol⁻¹ChemAxon
Polarizability21.4 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+147.16631661259
DarkChem[M-H]-146.31331661259
DeepCCS[M+H]+150.04230932474
DeepCCS[M-H]-147.64630932474
DeepCCS[M-2H]-181.03330932474
DeepCCS[M+Na]+156.00630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethsuximideCN1C(=O)CC(C)(C1=O)C1=CC=CC=C12627.3Standard polar33892256
MethsuximideCN1C(=O)CC(C)(C1=O)C1=CC=CC=C11619.3Standard non polar33892256
MethsuximideCN1C(=O)CC(C)(C1=O)C1=CC=CC=C11607.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methsuximide EI-B (Non-derivatized)splash10-014i-3910000000-9cae394b5b94a483c4012017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methsuximide CI-B (Non-derivatized)splash10-0udi-0090000000-31b6e0b0429306f0d6da2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methsuximide CI-B (Non-derivatized)splash10-0udi-0490000000-37eb2b7cfbb3d8b42e972017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methsuximide EI-B (Non-derivatized)splash10-014i-3910000000-9cae394b5b94a483c4012018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methsuximide CI-B (Non-derivatized)splash10-0udi-0090000000-31b6e0b0429306f0d6da2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methsuximide CI-B (Non-derivatized)splash10-0udi-0490000000-37eb2b7cfbb3d8b42e972018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methsuximide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxr-0900000000-e0b7a163d2486262e40a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methsuximide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methsuximide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-4910000000-aa3742fc04cdbcda351f2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methsuximide LC-ESI-QFT , positive-QTOFsplash10-0udi-0390000000-00d729cf9e85b7d750682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methsuximide LC-ESI-QFT , positive-QTOFsplash10-0udi-1690000000-0a263ad37a0831b81fb32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methsuximide LC-ESI-QFT , positive-QTOFsplash10-014i-4910000000-eb0a383017c0566e6a112017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methsuximide LC-ESI-QFT , positive-QTOFsplash10-014l-9800000000-5df2aae06682d9488eef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methsuximide LC-ESI-QFT , positive-QTOFsplash10-05mo-9400000000-6de622fc3efce00a0b342017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methsuximide LC-ESI-QFT , positive-QTOFsplash10-052f-9300000000-1e2faae8b516a3fc7ad52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methsuximide 45V, Positive-QTOFsplash10-014i-4910000000-3edaee012b8d0ab6abab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methsuximide 15V, Positive-QTOFsplash10-0udi-0290000000-7e1ec4ffc809d1b17f692021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methsuximide 30V, Positive-QTOFsplash10-0udi-1690000000-634173d911d8c9526bda2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methsuximide 60V, Positive-QTOFsplash10-014l-9800000000-fe9ec2e272ddfa8521022021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methsuximide 75V, Positive-QTOFsplash10-05mo-9400000000-0014609b9f8d422ac9b12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methsuximide 90V, Positive-QTOFsplash10-052f-9200000000-4e2b70d601f365fae12e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methsuximide 10V, Positive-QTOFsplash10-0udi-0090000000-7bd86034fa816a0243c32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methsuximide 20V, Positive-QTOFsplash10-0udi-0190000000-4ce7c75dd0aecca4396f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methsuximide 40V, Positive-QTOFsplash10-0ufr-9600000000-bf46c29670f52d82e8ab2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methsuximide 10V, Negative-QTOFsplash10-0udi-0090000000-e3773732d15693b117d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methsuximide 20V, Negative-QTOFsplash10-0udi-1190000000-d519c86bfcc321cacfa42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methsuximide 40V, Negative-QTOFsplash10-0udi-6900000000-7c462fe20661937889fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methsuximide 10V, Positive-QTOFsplash10-0udi-0090000000-b81b75e675178531e9bb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methsuximide 20V, Positive-QTOFsplash10-0udi-1960000000-8ff948008064ff6c3bf32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methsuximide 40V, Positive-QTOFsplash10-014l-8900000000-b05d83746feabe3e2ce42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methsuximide 10V, Negative-QTOFsplash10-0udi-0090000000-341f1e0a28e483a04bd32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methsuximide 20V, Negative-QTOFsplash10-0ufr-6920000000-366e7547f18799baaf742021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methsuximide 40V, Negative-QTOFsplash10-004i-9100000000-675b081ad6d6943d7c752021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB05246 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB05246 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB05246
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6231
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMesuximide
METLIN IDNot Available
PubChem Compound6476
PDB IDNot Available
ChEBI ID131857
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1540451
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Besag FM, Berry DJ, Pool F: Methsuximide lowers lamotrigine blood levels: A pharmacokinetic antiepileptic drug interaction. Epilepsia. 2000 May;41(5):624-7. [PubMed:10802770 ]
  2. Hurst DL: Methsuximide therapy of juvenile myoclonic epilepsy. Seizure. 1996 Mar;5(1):47-50. [PubMed:8777552 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in ion channel activity
Specific function:
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
Gene Name:
CACNA1G
Uniprot ID:
O43497
Molecular weight:
262468.6
References
  1. Gomora JC, Daud AN, Weiergraber M, Perez-Reyes E: Block of cloned human T-type calcium channels by succinimide antiepileptic drugs. Mol Pharmacol. 2001 Nov;60(5):1121-32. [PubMed:11641441 ]
  2. Coulter DA, Huguenard JR, Prince DA: Characterization of ethosuximide reduction of low-threshold calcium current in thalamic neurons. Ann Neurol. 1989 Jun;25(6):582-93. [PubMed:2545161 ]
  3. Wang G, Thompson SM: Maladaptive homeostatic plasticity in a rodent model of central pain syndrome: thalamic hyperexcitability after spinothalamic tract lesions. J Neurosci. 2008 Nov 12;28(46):11959-69. doi: 10.1523/JNEUROSCI.3296-08.2008. [PubMed:19005061 ]
  4. Matthews EA, Dickenson AH: Effects of ethosuximide, a T-type Ca(2+) channel blocker, on dorsal horn neuronal responses in rats. Eur J Pharmacol. 2001 Mar;415(2-3):141-9. [PubMed:11274992 ]