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Details

Stereochemistry RACEMIC
Molecular Formula C12H13NO2
Molecular Weight 203.2376
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHSUXIMIDE

SMILES

CC1(CC(=O)N(C)C1=O)c2ccccc2

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:: 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

-407030400000
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
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
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 [ORANGE BOOK]
Common Name English
METHSUXIMIDE [VANDF]
Common Name English
METHSUXIMIDE [USP]
Common Name English
MESUXIMIDE
INN   MART.   WHO-DD  
INN  
Official Name English
METHSUXIMIDE [MI]
Common Name English
Classification Tree Code System Code
LIVERTOX 622
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
WHO-VATC QN03AD03
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
NCI_THESAURUS C264
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
NDF-RT N0000008486
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
WHO-ATC N03AD03
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
NDF-RT N0000175753
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C47613
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PRIMARY
EPA CompTox
77-41-8
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY
USP_CATALOG
1422001
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY USP-RS
HSDB
3124
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PRIMARY
RXCUI
47858
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PRIMARY RxNorm
DRUG BANK
DB05246
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PRIMARY
MESH
C100286
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PRIMARY
MERCK INDEX
M7348
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL697
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY
WIKIPEDIA
MESUXIMIDE
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY
INN
582
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY
EVMPD
SUB08797MIG
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY
FDA UNII
0G76K8X6C0
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY
PUBCHEM
6476
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY
DRUG CENTRAL
1758
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY
IUPHAR
7228
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY
CAS
77-41-8
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-026-7
Created by admin on Fri Jun 25 21:53:51 UTC 2021 , Edited by admin on Fri Jun 25 21:53:51 UTC 2021
PRIMARY