Trimethadione

Trimethadione

Systematic (IUPAC) name
3,5,5-trimethyl-1,3-oxazolidine-2,4-dione
Clinical data
Trade names	Tridione
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy cat.	X
Legal status	℞ Prescription only
Routes	Oral
Pharmacokinetic data
Bioavailability	High
Metabolism	Demethylated to dimethadione
Half-life	12–24 hours (trimethadione) 6–13 days (dimethadione)
Excretion	Renal
Identifiers
CAS number	127-48-0 Y
ATC code	N03AC02
PubChem	CID 5576
DrugBank	DB00347
ChemSpider	5374 Y
UNII	R7GV3H6FQ4 Y
KEGG	D00392 Y
ChEMBL	CHEMBL695 Y
Chemical data
Formula	C6H9NO3
Mol. mass	143.141 g/mol
SMILES O=C1N(C(=O)OC1(C)C)C
InChI InChI=1S/C6H9NO3/c1-6(2)4(8)7(3)5(9)10-6/h1-3H3 Y Key:IRYJRGCIQBGHIV-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

Trimethadione is an oxazolidinedione anticonvulsant. It is most commonly used to treat epileptic conditions that are resistant to other treatments.

Fetal trimethadione syndrome

If administered during pregnancy, fetal trimethadione syndrome may result causing facial dysmorphism (short upturned nose, slanted eyebrows), cardiac defects, intrauterine growth retardation (IUGR), and mental retardation. The fetal loss rate while using trimethadione has been reported to be as high as 87%.^[1]

Chemistry

Trimethadione, 3,5,5-trimethyloxazolidine-2,4-dione, may be synthesized by methylating 5,5-trimethyloxazolidine-2,4-dione with dimethylsulfate. Starting 5,5-trimethyloxazolidine-2,4-dione is in turn synthesized by the cyclocondensation of the ester of 2-hydroxyisobutyric acid with urea.

• J.S.H. Davies, W. Hook, U.S. Patent 2,559,011 (1951).
• M.A. Spielman, U.S. Patent 2,575,692 (1951).
• Spielman, M. A. (1944). Journal of the American Chemical Society 66 (8): 1244–1245. doi:10.1021/ja01236a005. 

References

External links

• MedlinePlus DrugInfo medmaster-a601127
• DDB 30479