Human Metabolome Database: Showing metabocard for Ethosuximide (HMDB0014731)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

enzymes (6) Show 6 proteins

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2020-02-26 21:40:14 UTC

HMDB ID

HMDB0014731

Secondary Accession Numbers

HMDB14731

Metabolite Identification

Common Name

Ethosuximide

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-2-Ethyl-2-methylsuccinimide	ChEBI
2-Ethyl-2-methylsuccinimide	ChEBI
2-Methyl-2-ethylsuccinimide	ChEBI
3-Ethyl-3-methyl-2,5-pyrrolidinedione	ChEBI
3-Ethyl-3-methylsuccinimide	ChEBI
3-Methyl-3-ethylpyrrolidine-2,5-dione	ChEBI
3-Methyl-3-ethylsuccinimide	ChEBI
Aethosuximide	ChEBI
alpha-Ethyl-alpha-methylsuccinimide	ChEBI
alpha-Methyl-alpha-ethylsuccinimide	ChEBI
Ethosuximidum	ChEBI
Etosuximida	ChEBI
gamma-Ethyl-gamma-methyl-succinimide	ChEBI
gamma-Methyl-gamma-ethyl-succinimide	ChEBI
Zarontin	Kegg
a-Ethyl-a-methylsuccinimide	Generator
Α-ethyl-α-methylsuccinimide	Generator
a-Methyl-a-ethylsuccinimide	Generator
Α-methyl-α-ethylsuccinimide	Generator
g-Ethyl-g-methyl-succinimide	Generator
Γ-ethyl-γ-methyl-succinimide	Generator
g-Methyl-g-ethyl-succinimide	Generator
Γ-methyl-γ-ethyl-succinimide	Generator
Ethosuccimide	HMDB
Ethosuccinimide	HMDB
Ethosuxide	HMDB
Desitin brand OF ethosuximide	HMDB
Ethylmethylsuccimide	HMDB
LAB brand OF ethosuximide	HMDB
Parke davis brand OF ethosuximide	HMDB
Pyknolepsinum	HMDB
Suxilep	HMDB
Emeside	HMDB
Faes brand OF ethosuximide	HMDB
Katwijk brand OF ethosuximide	HMDB
Pfizer brand OF ethosuximide	HMDB
Warner lambert brand OF ethosuximide	HMDB
Warner-lambert brand OF ethosuximide	HMDB
Fortbenton brand OF ethosuximide	HMDB
Jenapharm brand OF ethosuximide	HMDB
Suksilep	HMDB
Ethosuccimid	HMDB
Ethymal	HMDB
Etosuximida faes	HMDB
Faes, etosuximida	HMDB
Petnidan	HMDB
United drug brand OF ethosuximide	HMDB
Wernigerode brand OF ethosuximide	HMDB

Chemical Formula

C₇H₁₁NO₂

Average Molecular Weight

141.1677

Monoisotopic Molecular Weight

141.078978601

IUPAC Name

3-ethyl-3-methylpyrrolidine-2,5-dione

Traditional Name

ethosuximide

CAS Registry Number

77-67-8

SMILES

CCC1(C)CC(=O)NC1=O

InChI Identifier

InChI=1S/C7H11NO2/c1-3-7(2)4-5(9)8-6(7)10/h3-4H2,1-2H3,(H,8,9,10)

InChI Key

HAPOVYFOVVWLRS-UHFFFAOYSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Pyrrolidones

Direct Parent

Pyrrolidine-2-ones

Alternative Parents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

pyrrolidinone (CHEBI:4887 )
dicarboximide (CHEBI:4887 )

Ontology

Physiological effect

Health effect:

Health condition:

Coma

Psychiatric disorders:

Depression

Gastrointestinal disorders:

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Drug

Pharmaceutical industry:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	64.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	101 g/L	Not Available
LogP	0.1	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	101 g/L	ALOGPS
logP	0.1	ALOGPS
logP	0.55	ChemAxon
logS	-0.15	ALOGPS
pKa (Strongest Acidic)	10.73	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.17 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.96 m³·mol⁻¹	ChemAxon
Polarizability	14.45 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-08mi-9400000000-44583cdc88d3203a4e84	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0006-1900000000-1c27ada66f7846f9d155	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0006-2900000000-19e57defe9ded4ed42b4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-08mi-9400000000-44583cdc88d3203a4e84	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0006-1900000000-1c27ada66f7846f9d155	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0006-2900000000-19e57defe9ded4ed42b4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9300000000-85b98f89652d40beec08	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-86a82d1f0e8a43f11ab5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-3900000000-e43cf4042ca22cb5d6a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0q29-9000000000-0593295be197f643992c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-7b6a825d9781021fd166	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-3900000000-a161e0f30f683c657129	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9000000000-25a91a77a1c19188305e	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-08mi-9300000000-3d87944377ee1f85803d	Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00593	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00593	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00593

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3175

KEGG Compound ID

C07505

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethosuximide

METLIN ID

Not Available

PubChem Compound

3291

PDB ID

Not Available

ChEBI ID

4887

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:1336826 ]
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. [PubMed:2169941 ]
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 ]
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. [PubMed:2710401 ]
Patsalos PN: Properties of antiepileptic drugs in the treatment of idiopathic generalized epilepsies. Epilepsia. 2005;46 Suppl 9:140-8. [PubMed:16302888 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

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 ]

Enzyme Details

2. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

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 ]

Enzyme Details

3. Cytochrome P450 3A43

General function:: Involved in monooxygenase activity
Specific function:: Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:: CYP3A43
Uniprot ID:: Q9HB55
Molecular weight:: 57756.285

References

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 ]

Enzyme Details

4. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

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 ]

Enzyme Details

5. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

References

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 ]

Enzyme Details

6. Voltage-dependent T-type calcium channel subunit alpha-1G

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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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 ]
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 ]
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 ]

Showing metabocard for Ethosuximide (HMDB0014731)

Structure for HMDB0014731 (Ethosuximide)

Enzymes

References

References

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