Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H14N2O3 |
Molecular Weight | 246.2619 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC1(C(=O)NC(=O)N(C)C1=O)C2=CC=CC=C2
InChI
InChIKey=ALARQZQTBTVLJV-UHFFFAOYSA-N
InChI=1S/C13H14N2O3/c1-3-13(9-7-5-4-6-8-9)10(16)14-12(18)15(2)11(13)17/h4-8H,3H2,1-2H3,(H,14,16,18)
DescriptionSources: https://www.drugs.com/pro/mephobarbital.html
Sources: https://www.drugs.com/pro/mephobarbital.html
Mephobarbital us a barbiturate derivative used primary as an anticonvulsant, but also as a sedative and anxiolytic. Marketing of mephobarbital was discontinued in 2012.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2427687 |
19.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | MEBARAL Approved UseMephobarbital tablets are indicated for use as a sedative for the relief of anxiety, tension, and apprehension, and as an anticonvulsant for the treatment of grand mal and petit mal epilepsy. |
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Primary | MEBARAL Approved UseMephobarbital tablets are indicated for use as a sedative for the relief of anxiety, tension, and apprehension, and as an anticonvulsant for the treatment of grand mal and petit mal epilepsy. |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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0.24 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2249375 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPHOBARBITAL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.73 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2249375 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPHOBARBITAL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.29 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2249375 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPHOBARBITAL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.95 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2249375 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPHOBARBITAL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.05 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2249375 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPHOBARBITAL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.94 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2249375 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPHOBARBITAL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
32.6% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2083148 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPHOBARBITAL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Myasthenia gravis syndrome associated with trimethadione. | 1970 Jun 29 |
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Ependymoblastoma associated with prenatal exposure to diphenylhydantoin and methylphenobarbitone. | 1985 May 1 |
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Role of CYP2C19 in stereoselective hydroxylation of mephobarbital by human liver microsomes. | 2001 Jan |
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Prediction of adsorption from multicomponent solutions by activated carbon using single-solute parameters. Part II--Proposed equation. | 2002 |
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Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. | 2003 Jan 1 |
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Withdrawal of methylphenobarbitone. | 2003 Jan 6 |
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Determination of two ternary mixtures containing phenobarbitone by second derivative of the ratio spectrum-zero-crossing and HPLC methods. | 2003 May |
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Monolithic silica columns with chemically bonded beta-cyclodextrin as a stationary phase for enantiomer separations of chiral pharmaceuticals. | 2003 Nov |
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Key structural features of ligands for activation of human pregnane X receptor. | 2004 Apr |
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Pharmacogenetic roles of CYP2C19 and CYP2B6 in the metabolism of R- and S-mephobarbital in humans. | 2004 Aug |
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A novel single nucleotide polymorphism (SNP) of the CYP2C19 gene in a Japanese subject with lowered capacity of mephobarbital 4'-hydroxylation. | 2004 Jun |
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[Intoxication due to replacement of the precursor methylphenobarbital by phenobarbital]. | 2006 Apr 29 |
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Phenotype-genotype analysis of CYP2C19 in Colombian mestizo individuals. | 2007 Jul 11 |
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A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs. | 2009 |
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Monitoring antiepileptic drugs: a level-headed approach. | 2009 Jun |
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A high-throughput multivariate optimization for the simultaneous enantioseparation and detection of barbiturates in micellar electrokinetic chromatography-mass spectrometry. | 2010 Aug |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/mephobarbital.html
Mephobarbital shoudl be administered orally. For treatment of epilepsy the average dose for adults and children 12 years of age and older: 400 mg to 600 mg daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2427687
Uptake of [36]Cl- ions by membranes from mouse brain was measured using liquid scintillation spectrometry. Mephobarbital simulated GABA-dependent Cl- uptake with EC50 of 19 uM.
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2250
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WHO-ATC |
N03AA01
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C67084
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QN03AA01
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METHYLPHENOBARBITAL
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)