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Identification
NamePhensuximide
Accession NumberDB00832  (APRD00496)
TypeSmall Molecule
GroupsApproved
DescriptionPhensuximide is an anticonvulsant in the succinimide class. It suppresses the paroxysmal three cycle per second spike and wave EEG pattern associated with lapses of consciousness in petit mal seizures. The frequency of attacks is reduced by depression of nerve transmission in the motor cortex.
Structure
Thumb
Synonyms
Fensuccimide
Fensuximida
Milontin
Phensuximide
Phensuximidum
External Identifiers
  • P-D 393
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Lifene Debat
MilontinParke-Davis
MilontonBCM Corporation
SuccitimalKatwijk
Brand mixturesNot Available
SaltsNot Available
Categories
UNII6WVL9C355G
CAS number86-34-0
WeightAverage: 189.2105
Monoisotopic: 189.078978601
Chemical FormulaC11H11NO2
InChI KeyInChIKey=WLWFNJKHKGIJNW-UHFFFAOYSA-N
InChI
InChI=1S/C11H11NO2/c1-12-10(13)7-9(11(12)14)8-5-3-2-4-6-8/h2-6,9H,7H2,1H3
IUPAC Name
1-methyl-3-phenylpyrrolidine-2,5-dione
SMILES
CN1C(=O)CC(C1=O)C1=CC=CC=C1
Taxonomy
DescriptionThis compound 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
  • Dicarboximide
  • Benzenoid
  • N-alkylpyrrolidine
  • 2-pyrrolidone
  • Pyrrolidone
  • Carboxylic acid imide, n-substituted
  • Monocyclic benzene moiety
  • Pyrrole
  • Carboxylic acid imide
  • Tertiary amine
  • Lactam
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of epilepsy.
PharmacodynamicsPhensuximide suppresses the paroxysmal three cycle per second spike and wave EEG pattern associated with lapses of consciousness in absence (petit mal) seizures. The frequency of attacks is reduced by depression of nerve transmission in the motor cortex.
Mechanism of actionPhensuximide's mechanism of action not understood, but may act in inhibitory neuronal systems that are important in the generation of the three per second rhythm. It's effects may be related to its ability to inhibit depolarization-induced accumulation of cyclic AMP and cyclic GMP in brain tissue.
Related Articles
AbsorptionRapid and complete.
Volume of distributionNot Available
Protein binding21%
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9975
Caco-2 permeable+0.7241
P-glycoprotein substrateNon-substrate0.7832
P-glycoprotein inhibitor INon-inhibitor0.8907
P-glycoprotein inhibitor IINon-inhibitor0.9756
Renal organic cation transporterNon-inhibitor0.7072
CYP450 2C9 substrateNon-substrate0.7511
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9225
CYP450 2D6 inhibitorNon-inhibitor0.9251
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9805
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9612
Ames testNon AMES toxic0.9173
CarcinogenicityNon-carcinogens0.8879
BiodegradationReady biodegradable0.5277
Rat acute toxicity2.0330 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.981
hERG inhibition (predictor II)Non-inhibitor0.9646
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Parke davis div warner lambert co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point72 °CPhysProp
water solubility7020 mg/LNot Available
logP0.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.21 mg/mLALOGPS
logP0.61ALOGPS
logP0.91ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)19.4ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area37.38 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.85 m3·mol-1ChemAxon
Polarizability19.66 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.49 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. Rankin GO, Cressey-Veneziano K, Wang RT, Brown PI: Urinary tract effects of phensuximide in the Sprague-Dawley and Fischer 344 rat. J Appl Toxicol. 1986 Oct;6(5):349-56. [PubMed:3772011 ]
  2. CHEN G, WESTON JK, BRATTON AC Jr: Anticonvulsant activity and toxicity of phensuximide, methsuximide and ethosuximide. Epilepsia. 1963 Mar;4:66-76. [PubMed:14020499 ]
  3. Ferrendelli JA, Kinscherf DA: Inhibitory effects of anticonvulsant drugs on cyclic nucleotide accumulation in brain. Ann Neurol. 1979 Jun;5(6):533-8. [PubMed:38736 ]
External Links
ATC CodesN03AD02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Phensuximide.
MefloquineThe therapeutic efficacy of Phensuximide can be decreased when used in combination with Mefloquine.
MianserinThe therapeutic efficacy of Phensuximide can be decreased when used in combination with Mianserin.
OrlistatThe serum concentration of Phensuximide can be decreased when it is combined with Orlistat.
Food InteractionsNot Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase 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:
55930.545 Da
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23