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Methsuximide

July 24, 2017
Common Name

Methsuximide Description

Methsuximide is only found in individuals that have used or taken this drug. It is an anticonvlisant 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 particliarity 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 vascliar smooth muscle. They may also be involved in the modliation of firing patterns of neurons which is important for information processing as well as in cell growth processes. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 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 methsuximideMeSH Methsuximide, (+)-isomerMeSH Warner-lambert brand OF methsuximideMeSH MesuximidMeSH Parke david brand OF methsuximideMeSH Methsuximide, (-)-isomerMeSH PetinutinMeSH Methsuximide, (+-)-isomerMeSH

Chemical Formlia

C12H13NO2 Average Molecliar Weight

203.2371 Monoisotopic Molecliar Weight

203.094628665 IUPAC Name

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

methsuximide CAS Registry Number

77-41-8 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 Key

AJXPJJZHWIXJCJ-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Pyrrolidines Direct Parent

Phenylpyrrolidines Alternative Parents

  • Pyrrolidine-2-ones
  • N-substituted carboxylic acid imides
  • N-alkylpyrrolidines
  • Benzene and substituted derivatives
  • Pyrroles
  • Dicarboximides
  • Lactams
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • 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

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anticonvlisants
  • Succinimides

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point52.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility2.13e+00 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility2.13 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count1ChemAxon Refractivity56.35 m3·mol-1ChemAxon Polarizability21.4 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0udi-0390000000-00d729cf9e85b7d75068View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0udi-1690000000-0a263ad37a0831b81fb3View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-014i-4910000000-eb0a383017c0566e6a11View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-014l-9800000000-5df2aae06682d9488eefView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-05mo-9400000000-6de622fc3efce00a0b34View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-052f-9300000000-1e2faae8b516a3fc7ad5View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

    Mass Spectrum (Electron Ionization)splash10-014i-4910000000-aa3742fc04cdbcda351fView in MoNA

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB05246

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB05246

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-5 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB05246 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    6231 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Methsuximide NuGOwiki Link

    HMDB15611 Metagene Link

    HMDB15611 METLIN ID

    Not Available PubChem Compound

    6476 PDB ID

    Not Available ChEBI ID

    131857

    Product: Ibandronate (Sodium)

    References Synthesis Reference Not 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 ]

    PMID: 8901026

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