U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C12H13NO2
Molecular Weight 203.2371
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHSUXIMIDE

SMILES

CN1C(=O)CC(C)(C1=O)C2=CC=CC=C2

InChI

InChIKey=AJXPJJZHWIXJCJ-UHFFFAOYSA-N
InChI=1S/C12H13NO2/c1-12(9-6-4-3-5-7-9)8-10(14)13(2)11(12)15/h3-7H,8H2,1-2H3

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/010596s22lbl.pdf

Mesuximide (or methsuximide) is an anticonvulsant medication. It is sold by Pfizer under the name Petinutin. 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. Mesuximide is used for the control of absence (petit mal) seizures that are refractory to other drugs.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Celontin

Approved Use

Celontin is indicated for the control of absence (petit mal) seizures that are refractory to other drugs.

Launch Date

1957
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
39.5 mg/L
11.1 mg/kg 2 times / day steady-state, oral
dose: 11.1 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
N-DESMETHYLMETHSUXIMIDE serum
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
25.6 h
11.1 mg/kg 2 times / day steady-state, oral
dose: 11.1 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
N-DESMETHYLMETHSUXIMIDE serum
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
55%
steady-state, unknown
N-DESMETHYLMETHSUXIMIDE serum
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
weak
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Methsuximide overdose. Delayed onset of profound coma.
1973 Mar 26
Carbamazepine-induced choreoathetoid dyskinesias.
1982 Jun
Methsuximide therapy of juvenile myoclonic epilepsy.
1996 Mar
Methsuximide lowers lamotrigine blood levels: A pharmacokinetic antiepileptic drug interaction.
2000 May
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

A suggested dosage schedule is 300 mg per day for the first week. If required, dosage may be increased thereafter at weekly intervals by 300 mg per day for the three weeks following to a daily dosage of 1.2 g. Because therapeutic effect and tolerance vary among patients, therapy with Celontin must be individualized according to the response of each patient
Route of Administration: Oral
In Vitro Use Guide
Methsuximide (50 and 100 uM) inhibited cycloguanil formation by 68% and 77% and chlorcycloguanil formation by 43% and 58%, respectively in human liver microsomes.
Name Type Language
METHSUXIMIDE
HSDB   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
2,5-PYRROLIDINEDIONE,1,3-DIMETHYL-3-PHENYL-, (±)-
Common Name English
METHSUXIMIDE [USP-RS]
Common Name English
CELONTIN
Brand Name English
(±)-N,2-DIMETHYL-2-PHENYLSUCCINIMIDE
Systematic Name English
MESUXIMIDE [MART.]
Common Name English
mesuximide [INN]
Common Name English
Mesuximide [WHO-DD]
Common Name English
NSC-760075
Code English
METHSUXIMIDE [HSDB]
Common Name English
METHSUXIMIDE [USP MONOGRAPH]
Common Name English
METHSUXIMIDE [ORANGE BOOK]
Common Name English
METHSUXIMIDE [VANDF]
Common Name English
MESUXIMIDE
INN   MART.   WHO-DD  
INN  
Official Name English
METHSUXIMIDE [MI]
Common Name English
Classification Tree Code System Code
LIVERTOX NBK548535
Created by admin on Fri Dec 15 14:59:35 GMT 2023 , Edited by admin on Fri Dec 15 14:59:35 GMT 2023
WHO-VATC QN03AD03
Created by admin on Fri Dec 15 14:59:35 GMT 2023 , Edited by admin on Fri Dec 15 14:59:35 GMT 2023
NCI_THESAURUS C264
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NDF-RT N0000008486
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WHO-ATC N03AD03
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NDF-RT N0000175753
Created by admin on Fri Dec 15 14:59:35 GMT 2023 , Edited by admin on Fri Dec 15 14:59:35 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C47613
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PRIMARY
EPA CompTox
DTXSID5023293
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PRIMARY
NSC
760075
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PRIMARY
HSDB
3124
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PRIMARY
RXCUI
47858
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PRIMARY RxNorm
DRUG BANK
DB05246
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PRIMARY
SMS_ID
100000091385
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PRIMARY
DAILYMED
0G76K8X6C0
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PRIMARY
MESH
C100286
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PRIMARY
MERCK INDEX
m7348
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PRIMARY Merck Index
ChEMBL
CHEMBL697
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PRIMARY
WIKIPEDIA
MESUXIMIDE
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PRIMARY
INN
582
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PRIMARY
EVMPD
SUB08797MIG
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PRIMARY
RS_ITEM_NUM
1422001
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PRIMARY
FDA UNII
0G76K8X6C0
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PRIMARY
PUBCHEM
6476
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PRIMARY
DRUG CENTRAL
1758
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PRIMARY
IUPHAR
7228
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PRIMARY
CAS
77-41-8
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PRIMARY
ECHA (EC/EINECS)
201-026-7
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PRIMARY