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
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
DescriptionSources: http://www.drugbank.ca/drugs/DB05246Curator's Comment: Description was created based on several sources, including
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/010596s22lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB05246
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2362995 Sources: http://www.drugbank.ca/drugs/DB05246 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Celontin Approved UseCelontin is indicated for the control of absence (petit mal) seizures that are refractory to other drugs. Launch Date1957 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
55% |
steady-state, unknown |
N-DESMETHYLMETHSUXIMIDE serum | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
weak |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1365133/pdf/brjclinpharm00010-0099.pdf#page=1 Page: 1.0 |
major | |||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Methsuximide overdose. Delayed onset of profound coma. | 1973 Mar 26 |
|
Carbamazepine-induced choreoathetoid dyskinesias. | 1982 Jun |
|
Methsuximide therapy of juvenile myoclonic epilepsy. | 1996 Mar |
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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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7640152
Methsuximide (50 and 100 uM) inhibited cycloguanil formation by 68% and 77% and chlorcycloguanil formation by 43% and 58%, respectively in human liver microsomes.
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LIVERTOX |
NBK548535
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WHO-VATC |
QN03AD03
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NCI_THESAURUS |
C264
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N0000008486
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WHO-ATC |
N03AD03
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NDF-RT |
N0000175753
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C47613
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DTXSID5023293
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760075
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47858
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DB05246
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100000091385
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0G76K8X6C0
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C100286
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m7348
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CHEMBL697
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MESUXIMIDE
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582
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SUB08797MIG
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ACTIVE MOIETY