NAV

Phensuximide

Identification

Generic Name
Phensuximide
DrugBank Accession Number
DB00832
Background

Phensuximide is a member of the succinimide class with anticonvulsant properties. 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.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 189.2105
Monoisotopic: 189.078978601
Chemical Formula
C11H11NO2
Synonyms
  • Fensuccimide
  • Fensuximida
  • Phensuximide
  • Phensuximidum
External IDs
  • P-D 393
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Pharmacology

Indication

For the treatment of epilepsy.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Phensuximide 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 action

Phensuximide'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.

Absorption

Rapid and complete.

Volume of distribution

Not Available

Protein binding

21%

Metabolism

Hepatic.

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Phensuximide is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Phensuximide.
AcetophenazineThe risk or severity of CNS depression can be increased when Phensuximide is combined with Acetophenazine.
AgomelatineThe risk or severity of CNS depression can be increased when Phensuximide is combined with Agomelatine.
AlfentanilThe risk or severity of CNS depression can be increased when Alfentanil is combined with Phensuximide.
Food Interactions
Not Available

Products

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International/Other Brands
Lifene (Debat) / Milontin (Parke-Davis) / Milonton (BCM Corporation) / Succitimal (Katwijk )

Categories

ATC Codes
N03AD02 — Phensuximide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolidines
Sub Class
Phenylpyrrolidines
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
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Substituents
2-pyrrolidone / 3-phenylpyrrolidine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid imide / Carboxylic acid imide, n-substituted / Dicarboximide
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Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrrolidines (CHEBI:8079)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
6WVL9C355G
CAS number
86-34-0
InChI Key
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

References

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. [Article]
  2. CHEN G, WESTON JK, BRATTON AC Jr: Anticonvulsant activity and toxicity of phensuximide, methsuximide and ethosuximide. Epilepsia. 1963 Mar;4:66-76. [Article]
  3. Ferrendelli JA, Kinscherf DA: Inhibitory effects of anticonvulsant drugs on cyclic nucleotide accumulation in brain. Ann Neurol. 1979 Jun;5(6):533-8. [Article]
Human Metabolome Database
HMDB0014970
KEGG Drug
D00508
KEGG Compound
C07437
PubChem Compound
6839
PubChem Substance
46505695
ChemSpider
6578
BindingDB
50240063
RxNav
33309
ChEBI
8079
ChEMBL
CHEMBL797
PharmGKB
PA164771230
Wikipedia
Phensuximide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Parke davis div warner lambert co
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)72 °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 RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Download (7.49 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0f7o-4900000000-c4973d13cd54231e83f7
GC-MS Spectrum - EI-BGC-MSsplash10-0udi-3900000000-3ea0132a234fd8153646
GC-MS Spectrum - EI-BGC-MSsplash10-0udi-3900000000-ebb2c45214a57c99d4f6
GC-MS Spectrum - CI-BGC-MSsplash10-0006-0910000000-f0d2f8c20e993a067c81
GC-MS Spectrum - CI-BGC-MSsplash10-000i-0910000000-4a3cc5eeab3149bc14fb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-fd1f840bb9e114174c7e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-5e20526bf1c704593fb5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-ebe415ddb6cf6ba544ea
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-2900000000-8ecb517e3ab001c3ec21
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfu-5900000000-edaf4a1818e3dfde9db8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-2900000000-b39ac4df6b8a72dcf021
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-146.6257579
predicted
DarkChem Lite v0.1.0
[M-H]-140.49556
predicted
DeepCCS 1.0 (2019)
[M+H]+147.5749579
predicted
DarkChem Lite v0.1.0
[M+H]+142.89113
predicted
DeepCCS 1.0 (2019)
[M+Na]+146.9632579
predicted
DarkChem Lite v0.1.0
[M+Na]+150.04442
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:45