Trimethadione: Difference between revisions

Trimethadione
Clinical data
Trade names	Tridione
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	X;
Routes of; administration	Oral
ATC code	N03AC02 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	High
Metabolism	Demethylated to dimethadione
Elimination half-life	12–24 hours (trimethadione); 6–13 days (dimethadione)
Excretion	Renal
Identifiers
	IUPAC name 3,5,5-trimethyl-1,3-oxazolidine-2,4-dione;
CAS Number	127-48-0 ;
PubChem CID	5576;
DrugBank	DB00347 ;
ChemSpider	5374 ;
UNII	R7GV3H6FQ4;
KEGG	D00392 ;
ChEMBL	ChEMBL695 ;
CompTox Dashboard (EPA)	DTXSID9021396 ;
ECHA InfoCard	100.004.406
Chemical and physical data
Formula	C6H9NO3
Molar mass	143.141 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:IRYJRGCIQBGHIV-UHFFFAOYSA-N ;
	(verify)

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Revision as of 02:17, 20 February 2014

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.

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

References

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

J.S.H. Davies, W. Hook, U.S. patent 2,559,011 (1951).
M.A. Spielman, U.S. patent 2,575,692 (1951).
Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/ja01236a005, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/ja01236a005 instead.

External links

MedlinePlus DrugInfo medmaster-a601127
Diseases Database (DDB): 30479

This anticonvulsant-related article is a stub. You can help Wikipedia by expanding it.

[1] Teratology and Drug Use During Pregnancy Retrieved January 2007

[dimethadione_chemistry-2] "dimethadione monograph". Retrieved 19 February 2014.

[1]

[2]

@@ Line 60: / Line 60: @@
 <ref name="dimethadione chemistry">{{cite web | url=http://www.drugfuture.com/chemdata/dimethadione.html | title=dimethadione monograph | accessdate=19 February 2014}}</ref>
-*J.S.H. Davies, W. Hook, {{US Patent|2559011}} (1951).
-*M.A. Spielman, {{US Patent|2575692}} (1951).
-*{{Cite doi|10.1021/ja01236a005}}
 ==References==
 {{Reflist}}
+*J.S.H. Davies, W. Hook, {{US Patent|2559011}} (1951).
+*M.A. Spielman, {{US Patent|2575692}} (1951).
+*{{Cite doi|10.1021/ja01236a005}}
 ==External links==