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Details

Stereochemistry ACHIRAL
Molecular Formula C9H14N2O3
Molecular Weight 198.2194
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHARBITAL

SMILES

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

InChI

InChIKey=FWJKNZONDWOGMI-UHFFFAOYSA-N
InChI=1S/C9H14N2O3/c1-4-9(5-2)6(12)10-8(14)11(3)7(9)13/h4-5H2,1-3H3,(H,10,12,14)

HIDE SMILES / InChI
Methbarbital is a barbiturate anticonvulsant, discovered by Merck in 1905. It was introduced to market for treatment of epolepsy by Abbott in 1952, and discontinued in 1990.

Originator

Curator's Comment:: # Merck

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
GEMONIL

Approved Use

Long-acting barbiturate that is demethylated to barbital in the liver; has broad-spectrum anticonvulsant action, but used mainly to treat myoclonic spasms in infants.
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
Effects of barbiturates on human platelet aggregation differ depending on their chemical structures.
2003 Aug
Evaluation of pyridine-3-carboxylic acid as a drug carrier by utilizing multivariate methods, structure property correlations, and pattern recognition techniques.
2004
A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs.
2009
Monitoring antiepileptic drugs: a level-headed approach.
2009 Jun
Patents

Patents

Sample Use Guides

Metharbital is administered orally. Effective dose, causing a reduction in seizure score by 225, is 110 mg.
Route of Administration: Oral
In Vitro Use Guide
The binding of [3H]DHP (dihydropicrotoainin) to rat brain membrane fragments was measured by a centrifugation assay. Assay condition involved incubating 1-3 mg of protein at 0° for 15 min with 63 nM [3H]DHP with or without a given concentration of barbiturate in a total incubation medium of 2 ml. Following incubation, the vials were centrifuged, supernatant discarded, pellets rapidly rinsed, solubilized and prepared for counting as previously described (26) . Specific binding was obtained by subtracting from the total radioactivity in the pellet the background, i .e . the amount not displaced by high concentrations (0.1 mM) of unlabeled DHP. Metharbital inhibits binding of [3H]DHP to GABAA receptor with IC50 of 10 uM.
Name Type Language
METHARBITAL
INN   JAN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
METHARBITAL [INN]
Common Name English
2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5,5-DIETHYL-1-METHYL-
Systematic Name English
NSC-27156
Code English
METHARBITONE
Brand Name English
METHARBITAL [MART.]
Common Name English
5,5-DIETHYL-1-METHYLBARBITURIC ACID
Systematic Name English
METHARBITAL [VANDF]
Common Name English
METHARBITAL CIII
USP-RS  
Common Name English
METHARBITAL [WHO-DD]
Common Name English
METHARBITAL [ORANGE BOOK]
Common Name English
METHARBITAL [JAN]
Common Name English
GEMONIL
Brand Name English
METHARBITAL [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67084
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
WHO-VATC QN03AA30
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
WHO-ATC N03AA30
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
Code System Code Type Description
WIKIPEDIA
METHARBITAL
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
MESH
C084822
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
MERCK INDEX
M7303
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY Merck Index
IUPHAR
7230
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
RXCUI
6825
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY RxNorm
EPA CompTox
50-11-3
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
INN
2
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-011-2
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
DRUG CENTRAL
1740
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
DRUG BANK
DB00463
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
FDA UNII
02OS7K758T
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
CAS
50-11-3
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
ChEMBL
CHEMBL450
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
PUBCHEM
4099
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
NCI_THESAURUS
C66113
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY
EVMPD
SUB08841MIG
Created by admin on Sat Jun 26 13:07:49 UTC 2021 , Edited by admin on Sat Jun 26 13:07:49 UTC 2021
PRIMARY