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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
Structure of MEPHOBARBITAL

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)

HIDE SMILES / InChI
Molecular Formula C13H14N2O3
Molecular Weight 246.2619
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

Originator

Approval Year

1921
1467
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1430
 19.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
Approved
8429
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737
substrate
1037
substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1537

MRP1
107

CYP2C19
991

CYP2B6
664

CYP1A1
349

CYP1A2
1054

CYP2A6
543

CYP2C8
693

CYP2E1
667
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A1
349
 no
CYP1A2
1054
 no
CYP2A6
543
 no
CYP2C8
693
 no
CYP2C9
1037
 no
CYP2D6
1217
 no
CYP2E1
667
 no
CYP3A4
1737
 no
MRP1
107
 no
P-gp
1537
 no
CYP2B6
664
 yes
CYP2C19
991
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:6758
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6758
eMolecules
2729386
https://www.emolecules.com/cgi-bin/more?vid=2729386
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

Patents

GB339937
1
JP2007525670A
148

Sample Use Guides

In Vivo Use Guide
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 Dec 15 17:52:54 GMT 2023
Edited
by admin
on Fri Dec 15 17:52:54 GMT 2023
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
MEPHOBARBITAL [HSDB]
Common Name English
Methylphenobarbital [WHO-DD]
Common Name English
METHYLPHENOBARBITAL [MART.]
Common Name English
Classification Tree Code System Code
DEA NO. 2250
Created by admin on Fri Dec 15 17:52:54 GMT 2023 , Edited by admin on Fri Dec 15 17:52:54 GMT 2023
WHO-ATC N03AA01
Created by admin on Fri Dec 15 17:52:54 GMT 2023 , Edited by admin on Fri Dec 15 17:52:54 GMT 2023
NCI_THESAURUS C67084
Created by admin on Fri Dec 15 17:52:55 GMT 2023 , Edited by admin on Fri Dec 15 17:52:55 GMT 2023
WHO-VATC QN03AA01
Created by admin on Fri Dec 15 17:52:55 GMT 2023 , Edited by admin on Fri Dec 15 17:52:55 GMT 2023
Code System Code Type Description
RXCUI
6758
Created by admin on Fri Dec 15 17:52:55 GMT 2023 , Edited by admin on Fri Dec 15 17:52:55 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB00849
Created by admin on Fri Dec 15 17:52:54 GMT 2023 , Edited by admin on Fri Dec 15 17:52:54 GMT 2023
PRIMARY
DRUG CENTRAL
1696
Created by admin on Fri Dec 15 17:52:54 GMT 2023 , Edited by admin on Fri Dec 15 17:52:54 GMT 2023
PRIMARY
EVMPD
SUB08871MIG
Created by admin on Fri Dec 15 17:52:54 GMT 2023 , Edited by admin on Fri Dec 15 17:52:54 GMT 2023
PRIMARY
CAS
115-38-8
Created by admin on Fri Dec 15 17:52:54 GMT 2023 , Edited by admin on Fri Dec 15 17:52:54 GMT 2023
PRIMARY
MESH
D008618
Created by admin on Fri Dec 15 17:52:55 GMT 2023 , Edited by admin on Fri Dec 15 17:52:55 GMT 2023
PRIMARY
PUBCHEM
8271
Created by admin on Fri Dec 15 17:52:55 GMT 2023 , Edited by admin on Fri Dec 15 17:52:55 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-085-7
Created by admin on Fri Dec 15 17:52:54 GMT 2023 , Edited by admin on Fri Dec 15 17:52:54 GMT 2023
PRIMARY
MERCK INDEX
m7191
Created by admin on Fri Dec 15 17:52:55 GMT 2023 , Edited by admin on Fri Dec 15 17:52:55 GMT 2023
PRIMARY Merck Index
SMS_ID
100000090522
Created by admin on Fri Dec 15 17:52:55 GMT 2023 , Edited by admin on Fri Dec 15 17:52:55 GMT 2023
PRIMARY
HSDB
3579
Created by admin on Fri Dec 15 17:52:54 GMT 2023 , Edited by admin on Fri Dec 15 17:52:54 GMT 2023
PRIMARY
NCI_THESAURUS
C76528
Created by admin on Fri Dec 15 17:52:55 GMT 2023 , Edited by admin on Fri Dec 15 17:52:55 GMT 2023
PRIMARY
CHEBI
6758
Created by admin on Fri Dec 15 17:52:54 GMT 2023 , Edited by admin on Fri Dec 15 17:52:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL45029
Created by admin on Fri Dec 15 17:52:54 GMT 2023 , Edited by admin on Fri Dec 15 17:52:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID4023258
Created by admin on Fri Dec 15 17:52:54 GMT 2023 , Edited by admin on Fri Dec 15 17:52:54 GMT 2023
PRIMARY
INN
2901
Created by admin on Fri Dec 15 17:52:55 GMT 2023 , Edited by admin on Fri Dec 15 17:52:55 GMT 2023
PRIMARY
FDA UNII
5NC67NU76B
Created by admin on Fri Dec 15 17:52:54 GMT 2023 , Edited by admin on Fri Dec 15 17:52:54 GMT 2023
PRIMARY
RS_ITEM_NUM
1386000
Created by admin on Fri Dec 15 17:52:55 GMT 2023 , Edited by admin on Fri Dec 15 17:52:55 GMT 2023
PRIMARY
WIKIPEDIA
METHYLPHENOBARBITAL
Created by admin on Fri Dec 15 17:52:55 GMT 2023 , Edited by admin on Fri Dec 15 17:52:55 GMT 2023
PRIMARY
Related Record Type Details
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of PHENOBARBITAL
METABOLITE -> PARENT
Structure of 4-HYDROXYMEPHOBARBITAL
METABOLITE -> PARENT
Related Record Type Details
Structure of PHENOBARBITAL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of MEPHOBARBITAL
ACTIVE MOIETY
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