Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:27:13 UTC |
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Update Date | 2014-12-24 20:25:52 UTC |
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Accession Number | T3D2834 |
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Identification |
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Common Name | Ethosuximide |
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Class | Small Molecule |
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Description | Ethosuximide is only found in individuals that have used or taken this drug. It is an anticonvulsant especially useful in the treatment of absence seizures unaccompanied by other types of seizures. [PubChem]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. |
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Compound Type | - Amide
- Amine
- Anticonvulsant
- Drug
- Metabolite
- Organic Compound
- Succinimide
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | (+-)-2-Ethyl-2-methylsuccinimide | (±)-2-ethyl-2-methylsuccinimide | 2-ethyl-2-methylsuccinimide | 2-Methyl-2-ethylsuccinimide | 3-ethyl-3-methyl-2,5-pyrrolidinedione | 3-Ethyl-3-methylsuccinimide | 3-Methyl-3-ethylpyrrolidine-2,5-dione | 3-Methyl-3-ethylsuccinimide | Aethosuximide | alpha-Ethyl-alpha-methylsuccinimide | alpha-Methyl-alpha-ethylsuccinimide | Atysmal | Emeside | Ethosuccimide | Ethosuccinimide | Ethosuxide | Ethosuximid | Ethosuximidum | Ethymal | Etosuximida | Etoxin | gamma-Ethyl-gamma-methyl-succinimide | gamma-Methyl-gamma-ethyl-succinimide | Petimid | Petinimid | Petnidan | Suxilep | Suxinutin | Thilopemal | Zarondan | Zarontin | γ-ethyl-γ-methyl-succinimide |
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Chemical Formula | C7H11NO2 |
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Average Molecular Mass | 141.168 g/mol |
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Monoisotopic Mass | 141.079 g/mol |
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CAS Registry Number | 77-67-8 |
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IUPAC Name | 3-ethyl-3-methylpyrrolidine-2,5-dione |
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Traditional Name | ethosuximide |
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SMILES | CCC1(C)CC(O)=NC1=O |
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InChI Identifier | InChI=1/C7H11NO2/c1-3-7(2)4-5(9)8-6(7)10/h3-4H2,1-2H3,(H,8,9,10) |
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InChI Key | InChIKey=HAPOVYFOVVWLRS-UHFFFAOYNA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyrrolidines |
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Sub Class | Pyrrolidones |
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Direct Parent | Pyrrolidine-2-ones |
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Alternative Parents | |
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Substituents | - 2-pyrrolidone
- Carboxylic acid imide
- Dicarboximide
- Carboxylic acid imide, n-unsubstituted
- Lactam
- Carboxylic acid derivative
- Azacycle
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 64.5°C | Boiling Point | Not Available | Solubility | 39.2 g/L | LogP | 0.38 |
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Predicted Properties | |
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Spectra |
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Spectra | |
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Toxicity Profile |
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Route of Exposure | Bioavailability following oral administration is 93%. |
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Mechanism of Toxicity | 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. |
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Metabolism | Hepatic, via CYP3A4 and CYP2E1.
Half Life: 53 hours |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | For the treatment of petit mal epilepsy. |
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Minimum Risk Level | Not Available |
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Health Effects | May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease. |
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Symptoms | Acute overdoses may produce nausea, vomiting, and CNS depression including coma with respiratory depression. |
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Treatment | Treatment should include emesis (unless the patient is or could rapidly become obtunded, comatose, or convulsing) or gastric lavage, activated charcoal, cathartics, and general supportive measures. Hemodialysis may be useful to treat ethosuximide overdose. Forced diuresis and exchange transfusions are ineffective. (7) |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00593 |
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HMDB ID | HMDB14731 |
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PubChem Compound ID | 3291 |
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ChEMBL ID | CHEMBL696 |
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ChemSpider ID | 3175 |
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KEGG ID | C07505 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 4887 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Ethosuximide |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Ethosuximide |
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References |
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Synthesis Reference | Miller, C.A. and Long, L.M.; U.S. Patent 2,993,835; July 25,1961; assigned to Parke, Davis and Company. |
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MSDS | Link |
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General References | - Patsalos PN: Properties of antiepileptic drugs in the treatment of idiopathic generalized epilepsies. Epilepsia. 2005;46 Suppl 9:140-8. [16302888 ]
- Coulter DA, Huguenard JR, Prince DA: Specific petit mal anticonvulsants reduce calcium currents in thalamic neurons. Neurosci Lett. 1989 Mar 13;98(1):74-8. [2710401 ]
- 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. [2545161 ]
- Coulter DA, Huguenard JR, Prince DA: Differential effects of petit mal anticonvulsants and convulsants on thalamic neurones: calcium current reduction. Br J Pharmacol. 1990 Aug;100(4):800-6. [2169941 ]
- Kostyuk PG, Molokanova EA, Pronchuk NF, Savchenko AN, Verkhratsky AN: Different action of ethosuximide on low- and high-threshold calcium currents in rat sensory neurons. Neuroscience. 1992 Dec;51(4):755-8. [1336826 ]
- Drugs.com [Link]
- RxList: The Internet Drug Index (2009). [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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