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
- Weight
- Average: 189.2105
Monoisotopic: 189.078978601 - Chemical Formula
- C11H11NO2
- Synonyms
- Fensuccimide
- Fensuximida
- Phensuximide
- Phensuximidum
- External IDs
- P-D 393
Pharmacology
- Indication
For the treatment of epilepsy.
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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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Phensuximide is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Phensuximide. Acetophenazine The risk or severity of CNS depression can be increased when Phensuximide is combined with Acetophenazine. Agomelatine The risk or severity of CNS depression can be increased when Phensuximide is combined with Agomelatine. Alfentanil The 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 show 3 more
- Substituents
- 2-pyrrolidone / 3-phenylpyrrolidine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid imide / Carboxylic acid imide, n-substituted / Dicarboximide show 12 more
- 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
- 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]
- CHEN G, WESTON JK, BRATTON AC Jr: Anticonvulsant activity and toxicity of phensuximide, methsuximide and ethosuximide. Epilepsia. 1963 Mar;4:66-76. [Article]
- Ferrendelli JA, Kinscherf DA: Inhibitory effects of anticonvulsant drugs on cyclic nucleotide accumulation in brain. Ann Neurol. 1979 Jun;5(6):533-8. [Article]
- External Links
- Human Metabolome Database
- HMDB0014970
- KEGG Drug
- D00508
- KEGG Compound
- C07437
- PubChem Compound
- 6839
- PubChem Substance
- 46505695
- ChemSpider
- 6578
- BindingDB
- 50240063
- 33309
- ChEBI
- 8079
- ChEMBL
- CHEMBL797
- PharmGKB
- PA164771230
- Wikipedia
- Phensuximide
Clinical Trials
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
Property Value Source melting point (°C) 72 °C PhysProp water solubility 7020 mg/L Not Available logP 0.7 Not Available - Predicted Properties
Property Value Source Water Solubility 2.21 mg/mL ALOGPS logP 0.61 ALOGPS logP 0.91 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 19.4 Chemaxon pKa (Strongest Basic) -7.4 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 51.85 m3·mol-1 Chemaxon Polarizability 19.66 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 - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9975 Caco-2 permeable + 0.7241 P-glycoprotein substrate Non-substrate 0.7832 P-glycoprotein inhibitor I Non-inhibitor 0.8907 P-glycoprotein inhibitor II Non-inhibitor 0.9756 Renal organic cation transporter Non-inhibitor 0.7072 CYP450 2C9 substrate Non-substrate 0.7511 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9225 CYP450 2D6 inhibitor Non-inhibitor 0.9251 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9805 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9612 Ames test Non AMES toxic 0.9173 Carcinogenicity Non-carcinogens 0.8879 Biodegradation Ready biodegradable 0.5277 Rat acute toxicity 2.0330 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.981 hERG inhibition (predictor II) Non-inhibitor 0.9646
Spectra
- Mass Spec (NIST)
- Download (7.49 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 146.6257579 predictedDarkChem Lite v0.1.0 [M-H]- 140.49556 predictedDeepCCS 1.0 (2019) [M+H]+ 147.5749579 predictedDarkChem Lite v0.1.0 [M+H]+ 142.89113 predictedDeepCCS 1.0 (2019) [M+Na]+ 146.9632579 predictedDarkChem Lite v0.1.0 [M+Na]+ 150.04442 predictedDeepCCS 1.0 (2019)
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:45