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Details

Stereochemistry RACEMIC
Molecular Formula C13H14N2O3
Molecular Weight 246.2624
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPHOBARBITAL

SMILES

CCC1(c2ccccc2)C(=NC(=O)N(C)C1=O)O

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)

HIDE SMILES / InChI

Molecular Formula C13H14N2O3
Molecular Weight 246.2624
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Mephobarbital us a barbiturate derivative used primary as an anticonvulsant, but also as a sedative and anxiolytic. Marketing of mephobarbital was discontinued in 2012.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
19.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MEBARAL

Approved Use

Mephobarbital 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.
Primary
MEBARAL

Approved Use

Mephobarbital 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

Cmax

ValueDoseCo-administeredAnalytePopulation
0.24 μg/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
1.29 μg × h/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3.05 h
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
32.6%
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

PubMed

TitleDatePubMed
Myasthenia gravis syndrome associated with trimethadione.
1970 Jun 29
Ependymoblastoma associated with prenatal exposure to diphenylhydantoin and methylphenobarbitone.
1985 May 1
Role of CYP2C19 in stereoselective hydroxylation of mephobarbital by human liver microsomes.
2001 Jan
Prediction of adsorption from multicomponent solutions by activated carbon using single-solute parameters. Part II--Proposed equation.
2002
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
Withdrawal of methylphenobarbitone.
2003 Jan 6
Determination of two ternary mixtures containing phenobarbitone by second derivative of the ratio spectrum-zero-crossing and HPLC methods.
2003 May
Monolithic silica columns with chemically bonded beta-cyclodextrin as a stationary phase for enantiomer separations of chiral pharmaceuticals.
2003 Nov
Key structural features of ligands for activation of human pregnane X receptor.
2004 Apr
Pharmacogenetic roles of CYP2C19 and CYP2B6 in the metabolism of R- and S-mephobarbital in humans.
2004 Aug
A novel single nucleotide polymorphism (SNP) of the CYP2C19 gene in a Japanese subject with lowered capacity of mephobarbital 4'-hydroxylation.
2004 Jun
The history of barbiturates a century after their clinical introduction.
2005 Dec
[Intoxication due to replacement of the precursor methylphenobarbital by phenobarbital].
2006 Apr 29
Phenotype-genotype analysis of CYP2C19 in Colombian mestizo individuals.
2007 Jul 11
A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs.
2009
Fetal malformations associated with the use of methylphenobarbital and carbamazepine during pregnancy. Two case reports and review of the literature.
2009
The influence of sulfur substituents on the molecular geometry and packing of thio derivatives of N-methylphenobarbital.
2009 Feb
Monitoring antiepileptic drugs: a level-headed approach.
2009 Jun
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

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
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:52:11 UTC 2021
Edited
by admin
on Fri Jun 25 20:52:11 UTC 2021
Record UNII
5NC67NU76B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEPHOBARBITAL
HSDB   JAN   MI   USP   VANDF  
Common Name English
MEPHOBARBITAL [USP MONOGRAPH]
Common Name English
METHYLPHENOBARBITAL
EP   INN   MART.   WHO-DD  
INN  
Official Name English
ISONAL
Common Name English
MEPHOBARBITAL CIV [USP-RS]
Common Name English
ENPHENEMAL
Common Name English
METHYLPHENOBARBITAL [EP MONOGRAPH]
Common Name English
METHYLPHENOBARBITONE
Common Name English
MEPHOBARBITAL [MI]
Common Name English
BARBITURIC ACID, 5-ETHYL-1-METHYL-5-PHENYL-
Systematic Name English
METHYLPHENOBARBITAL [INN]
Common Name English
MENTA-BAL
Brand Name English
MEPHOBARBITAL [JAN]
Common Name English
MEPHOBARBITAL CIV
USP-RS  
Common Name English
5-ETHYL-1-METHYL-5-PHENYLBARBITURIC ACID
Systematic Name English
PHEMETONE
Common Name English
MEBARAL
Brand Name English
2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-ETHYL-1-METHYL-5-PHENYL-
Systematic Name English
MEPHOBARBITAL [VANDF]
Common Name English
METYLFENEMAL
Common Name English
METHYLPHENOBARBITAL [WHO-DD]
Common Name English
MEPHOBARBITAL [HSDB]
Common Name English
METHYLPHENOBARBITAL [MART.]
Common Name English
Classification Tree Code System Code
DEA NO. 2250
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
WHO-ATC N03AA01
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
NCI_THESAURUS C67084
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
WHO-VATC QN03AA01
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
Code System Code Type Description
RXCUI
6758
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00849
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
DRUG CENTRAL
1696
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
EVMPD
SUB08871MIG
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
CAS
115-38-8
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
MESH
D008618
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
PUBCHEM
8271
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-085-7
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
MERCK INDEX
M7191
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY Merck Index
HSDB
3579
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
NCI_THESAURUS
C76528
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL45029
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
EPA CompTox
115-38-8
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
INN
2901
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
FDA UNII
5NC67NU76B
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
USP_CATALOG
1386000
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
METHYLPHENOBARBITAL
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
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METABOLITE -> PARENT
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ACTIVE MOIETY