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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
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
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
[Intoxication due to replacement of the precursor methylphenobarbital by phenobarbital].
2006 Apr 29
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.
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 UTC 2023 , Edited by admin on Fri Dec 15 17:52:54 UTC 2023
WHO-ATC N03AA01
Created by admin on Fri Dec 15 17:52:54 UTC 2023 , Edited by admin on Fri Dec 15 17:52:54 UTC 2023
NCI_THESAURUS C67084
Created by admin on Fri Dec 15 17:52:55 UTC 2023 , Edited by admin on Fri Dec 15 17:52:55 UTC 2023
WHO-VATC QN03AA01
Created by admin on Fri Dec 15 17:52:55 UTC 2023 , Edited by admin on Fri Dec 15 17:52:55 UTC 2023
Code System Code Type Description
RXCUI
6758
Created by admin on Fri Dec 15 17:52:55 UTC 2023 , Edited by admin on Fri Dec 15 17:52:55 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB00849
Created by admin on Fri Dec 15 17:52:54 UTC 2023 , Edited by admin on Fri Dec 15 17:52:54 UTC 2023
PRIMARY
DRUG CENTRAL
1696
Created by admin on Fri Dec 15 17:52:54 UTC 2023 , Edited by admin on Fri Dec 15 17:52:54 UTC 2023
PRIMARY
EVMPD
SUB08871MIG
Created by admin on Fri Dec 15 17:52:54 UTC 2023 , Edited by admin on Fri Dec 15 17:52:54 UTC 2023
PRIMARY
CAS
115-38-8
Created by admin on Fri Dec 15 17:52:54 UTC 2023 , Edited by admin on Fri Dec 15 17:52:54 UTC 2023
PRIMARY
MESH
D008618
Created by admin on Fri Dec 15 17:52:55 UTC 2023 , Edited by admin on Fri Dec 15 17:52:55 UTC 2023
PRIMARY
PUBCHEM
8271
Created by admin on Fri Dec 15 17:52:55 UTC 2023 , Edited by admin on Fri Dec 15 17:52:55 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-085-7
Created by admin on Fri Dec 15 17:52:54 UTC 2023 , Edited by admin on Fri Dec 15 17:52:54 UTC 2023
PRIMARY
MERCK INDEX
m7191
Created by admin on Fri Dec 15 17:52:55 UTC 2023 , Edited by admin on Fri Dec 15 17:52:55 UTC 2023
PRIMARY Merck Index
SMS_ID
100000090522
Created by admin on Fri Dec 15 17:52:55 UTC 2023 , Edited by admin on Fri Dec 15 17:52:55 UTC 2023
PRIMARY
HSDB
3579
Created by admin on Fri Dec 15 17:52:54 UTC 2023 , Edited by admin on Fri Dec 15 17:52:54 UTC 2023
PRIMARY
NCI_THESAURUS
C76528
Created by admin on Fri Dec 15 17:52:55 UTC 2023 , Edited by admin on Fri Dec 15 17:52:55 UTC 2023
PRIMARY
CHEBI
6758
Created by admin on Fri Dec 15 17:52:54 UTC 2023 , Edited by admin on Fri Dec 15 17:52:54 UTC 2023
PRIMARY
ChEMBL
CHEMBL45029
Created by admin on Fri Dec 15 17:52:54 UTC 2023 , Edited by admin on Fri Dec 15 17:52:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID4023258
Created by admin on Fri Dec 15 17:52:54 UTC 2023 , Edited by admin on Fri Dec 15 17:52:54 UTC 2023
PRIMARY
INN
2901
Created by admin on Fri Dec 15 17:52:55 UTC 2023 , Edited by admin on Fri Dec 15 17:52:55 UTC 2023
PRIMARY
FDA UNII
5NC67NU76B
Created by admin on Fri Dec 15 17:52:54 UTC 2023 , Edited by admin on Fri Dec 15 17:52:54 UTC 2023
PRIMARY
RS_ITEM_NUM
1386000
Created by admin on Fri Dec 15 17:52:55 UTC 2023 , Edited by admin on Fri Dec 15 17:52:55 UTC 2023
PRIMARY
WIKIPEDIA
METHYLPHENOBARBITAL
Created by admin on Fri Dec 15 17:52:55 UTC 2023 , Edited by admin on Fri Dec 15 17:52:55 UTC 2023
PRIMARY