DIMETHADIONE

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 Search

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

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b9322f58-ffcc-4831-5381-93a535b49a09 | https://www.ncbi.nlm.nih.gov/pubmed/12027905 | https://www.ncbi.nlm.nih.gov/pubmed/8925801 | https://www.ncbi.nlm.nih.gov/pubmed/2545161 | https://www.ncbi.nlm.nih.gov/pubmed/26465006 | https://www.ncbi.nlm.nih.gov/pubmed/26311034 | https://www.ncbi.nlm.nih.gov/pubmed/26375719 | https://www.ncbi.nlm.nih.gov/pubmed/6604142

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated T-type calcium channel 19 Target ID: CHEMBL2362995 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8925801 \| https://www.ncbi.nlm.nih.gov/pubmed/2545161 \| https://www.ncbi.nlm.nih.gov/pubmed/26465006	Blocker 555
HERG 99 Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12027905	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dravet syndrome 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26465006	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In Utero Exposure to a Cardiac Teratogen Causes Reversible Deficits in Postnatal Cardiovascular Function, But Altered Adaptation to the Burden of Pregnancy.	2015-11	26311034
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.	2014-12-04	25446330
In utero dimethadione exposure causes postnatal disruption in cardiac structure and function in the rat.	2014-12	25239635
Alterations in mouse embryo intracellular pH by DMO during culture impair implantation and fetal growth.	2010-08	20615756
Acidic and basic solutions dissolve protein plugs made of lithostathine complicating choledochal cyst/pancreaticobiliary maljunction.	2009-07	18989781
Review of levetiracetam, with a focus on the extended release formulation, as adjuvant therapy in controlling partial-onset seizures.	2009	19777068
Glucose loading precipitates focal lactic acidosis in the vulnerable medial thalamus of thiamine-deficient rats.	2008-03	18034292
Polytherapy with hERG-blocking antiepileptic drugs: increased risk for embryonic cardiac arrhythmia and teratogenicity.	2007-08	17584909
Embryonic cardiac arrhythmia and generation of reactive oxygen species: common teratogenic mechanism for IKr blocking drugs.	2007-07	17570632
Pharmacological evidence that stalk cell differentiation involves increases in the intracellular Ca(2+) and H(+) concentrations in Dictyostelium discoideum.	2007-04	17394603
Thoracic skeletal defects and cardiac malformations: a common epigenetic link?	2006-12	17315248
Interactive effects of cadmium and all-trans-retinoic acid on the induction of forelimb ectrodactyly in C57BL/6 mice.	2006-01	16369952
Discriminative power of an assay for automated in vitro screening of teratogens.	2004-08	15130609
Disruption of bovine oocytes and preimplantation embryos by urea and acidic pH.	2003-04	12741544
Embryonic arrhythmia by inhibition of HERG channels: a common hypoxia-related teratogenic mechanism for antiepileptic drugs?	2002-05	12027905
Selection of test chemicals for the ECVAM international validation study on in vitro embryotoxicity tests. European Centre for the Validation of Alternative Methods.	2002-04-25	11971754
The clinical importance of the trimethadione tolerance test as a method for quantitative assessment of hepatic functional reserve in patients with biliary atresia.	2001-12	11722678
Na(+)-dependent pH regulation by the amitochondriate protozoan parasite Giardia intestinalis.	2001-08-03	11297564
Altering intracellular pH disrupts development and cellular organization in preimplantation hamster embryos.	2001-06	11369617
Trimethadione N-demethylation by rat liver CYP2E1 in vitro.	1996-07	8865369

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:51:01 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:01 GMT 2025`
Record UNII	ALU9NPM703
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DIMETHADIONE

Official Name

English

AC 1198

Preferred 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

DIMETHADIONE [MI]

Common Name

English

Code System Code Type Description

CAS

695-53-4