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Details

Stereochemistry ACHIRAL
Molecular Formula C5H7NO3
Molecular Weight 129.114
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMETHADIONE

SMILES

CC1(C)OC(=O)NC1=O

InChI

InChIKey=JYJFNDQBESEHJQ-UHFFFAOYSA-N
InChI=1S/C5H7NO3/c1-5(2)3(7)6-4(8)9-5/h1-2H3,(H,6,7,8)

HIDE SMILES / InChI

Molecular Formula C5H7NO3
Molecular Weight 129.114
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Dimethadione (5,5-dimethyl-2,4-oxazolidinedione) is the N-demethylated metabolite of the anticonvulsant trimethadione. Dimethadione is considered to be a blocker of T-type calcium channel. Dimethadione also inhibits a specific potassium channel (Ikr) in HERG-transfected cells. It exerts teratogenic effect especially congenital heart defects. Dimethadione can be used for the measurement of regional tissue pH using positron emission tomography.

Originator

Curator's Comment: reference retrieved from www.drugfuture.com/chemdata/dimethadione.html

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Trimethadione N-demethylation by rat liver CYP2E1 in vitro.
1996 Jul
The clinical importance of the trimethadione tolerance test as a method for quantitative assessment of hepatic functional reserve in patients with biliary atresia.
2001 Dec
Altering intracellular pH disrupts development and cellular organization in preimplantation hamster embryos.
2001 Jun
Selection of test chemicals for the ECVAM international validation study on in vitro embryotoxicity tests. European Centre for the Validation of Alternative Methods.
2002 Mar-Apr
Disruption of bovine oocytes and preimplantation embryos by urea and acidic pH.
2003 Apr
Thoracic skeletal defects and cardiac malformations: a common epigenetic link?
2006 Dec
Polytherapy with hERG-blocking antiepileptic drugs: increased risk for embryonic cardiac arrhythmia and teratogenicity.
2007 Aug
Embryonic cardiac arrhythmia and generation of reactive oxygen species: common teratogenic mechanism for IKr blocking drugs.
2007 Jul
Glucose loading precipitates focal lactic acidosis in the vulnerable medial thalamus of thiamine-deficient rats.
2008 Mar
Acidic and basic solutions dissolve protein plugs made of lithostathine complicating choledochal cyst/pancreaticobiliary maljunction.
2009 Jul
Alterations in mouse embryo intracellular pH by DMO during culture impair implantation and fetal growth.
2010 Aug
In utero dimethadione exposure causes postnatal disruption in cardiac structure and function in the rat.
2014 Dec
In Utero Exposure to a Cardiac Teratogen Causes Reversible Deficits in Postnatal Cardiovascular Function, But Altered Adaptation to the Burden of Pregnancy.
2015 Nov

Sample Use Guides

To generate rats with resolved congenital heart defects, pregnant rats were administered distilled water or dimethadione [300 mg/kg b.i.d. on gestation day (gd) 9 and 10] and pups delivered naturally. In order to detect both pancreatic excretion of dimethadione (DMO), a weak organic acid, and the effect of pancreatic DMO on secretin-stimulated pancreatic secretion, DMO was given intravenously to dogs with pancreatic fistulae at a dose of 50, 100 and 200 mg/kg.
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:13:51 GMT 2023
Edited
by admin
on Fri Dec 15 15:13:51 GMT 2023
Record UNII
ALU9NPM703
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIMETHADIONE
INN   MI   USAN  
USAN   INN  
Official Name English
AC-1198
Code English
NSC-30152
Code English
NORTRIMETHADIONE
Common Name English
DIMETHADIONE [USAN]
Common Name English
BAY-1400Z
Code English
5,5-Dimethyl-2,4-oxazolidinedione
Systematic Name English
DMO
Code English
2,4-OXAZOLIDINEDIONE, 5,5-DIMETHYL-
Systematic Name English
dimethadione [INN]
Common Name English
BAX-1400Z
Code English
BAX 1400Z
Code English
EUPRACTONE
Common Name English
AC 1198
Code English
DIMETHADIONE [MI]
Common Name English
Code System Code Type Description
CAS
695-53-4
Created by admin on Fri Dec 15 15:13:51 GMT 2023 , Edited by admin on Fri Dec 15 15:13:51 GMT 2023
PRIMARY
SMS_ID
100000082641
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
EVMPD
SUB07170MIG
Created by admin on Fri Dec 15 15:13:51 GMT 2023 , Edited by admin on Fri Dec 15 15:13:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID2020478
Created by admin on Fri Dec 15 15:13:51 GMT 2023 , Edited by admin on Fri Dec 15 15:13:51 GMT 2023
PRIMARY
ChEMBL
CHEMBL1099
Created by admin on Fri Dec 15 15:13:51 GMT 2023 , Edited by admin on Fri Dec 15 15:13:51 GMT 2023
PRIMARY
NCI_THESAURUS
C171703
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
PUBCHEM
3081
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
ECHA (EC/EINECS)
211-781-4
Created by admin on Fri Dec 15 15:13:51 GMT 2023 , Edited by admin on Fri Dec 15 15:13:51 GMT 2023
PRIMARY
MESH
D004114
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
INN
1130
Created by admin on Fri Dec 15 15:13:51 GMT 2023 , Edited by admin on Fri Dec 15 15:13:51 GMT 2023
PRIMARY
MERCK INDEX
m4505
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY Merck Index
FDA UNII
ALU9NPM703
Created by admin on Fri Dec 15 15:13:51 GMT 2023 , Edited by admin on Fri Dec 15 15:13:51 GMT 2023
PRIMARY
NSC
30152
Created by admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
PRIMARY
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Dimethadione has anticonvulsant activity and has been used clinically in the treatment of petit mal epilepsy.
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