U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Description

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.

CNS Activity

Originator

Stoughton, R.W.
1
Curator's Comment: reference retrieved from www.drugfuture.com/chemdata/dimethadione.html

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
537
Blocker
537
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Trimethadione N-demethylation by rat liver CYP2E1 in vitro.
1996 Jul
Altering intracellular pH disrupts development and cellular organization in preimplantation hamster embryos.
2001 Jun
Disruption of bovine oocytes and preimplantation embryos by urea and acidic pH.
2003 Apr
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
Review of levetiracetam, with a focus on the extended release formulation, as adjuvant therapy in controlling partial-onset seizures.
2009
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
Maternal rat serum concentrations of dimethadione do not explain intra-litter differences in the incidence of dimethadione-induced birth defects, including novel findings in foetal lung.
2014 Dec 4
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

In Vivo Use Guide
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
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
ACTIVE MOIETY
Structure of DIMETHADIONE
PARENT (METABOLITE ACTIVE)
Structure of TRIMETHADIONE
PARENT (METABOLITE TOXIC)
Structure of CHLOROFORM
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966