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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

Molecular Formula C12H13NO2
Molecular Weight 203.2371
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Celontin

Cmax

ValueDoseCo-administeredAnalytePopulation
39.5 mg/L
11.1 mg/kg 2 times / day steady-state, oral
N-DESMETHYLMETHSUXIMIDE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
25.6 h
11.1 mg/kg 2 times / day steady-state, oral
N-DESMETHYLMETHSUXIMIDE serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
55%
steady-state, unknown
N-DESMETHYLMETHSUXIMIDE serum
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
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.
Substance Class Chemical
Record UNII
0G76K8X6C0
Record Status Validated (UNII)
Record Version