Trimethadione

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This article is about the drug Tridione. For the content management software Tridion, see SDL plc.
Trimethadione
Trimethadione.svg
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 YesY
ATC code N03AC02
PubChem CID 5576
DrugBank DB00347
ChemSpider 5374 YesY
UNII R7GV3H6FQ4 YesY
KEGG D00392 YesY
ChEMBL CHEMBL695 YesY
Chemical data
Formula C6H9NO3 
Mol. mass 143.141 g/mol
 YesY (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[edit]

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

Chemistry[edit]

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.

Trimethadione synthesis.png

Dimethadione is an active metabolite with anticonvulsant properties, used in determination of intracellular pH. [2]


References[edit]

  1. ^ Teratology and Drug Use During Pregnancy Retrieved January 2007
  2. ^ "dimethadione monograph". Retrieved 19 February 2014. 

External links[edit]