Paramethadione

Paramethadione

Systematic (IUPAC) name
(RS)-5-ethyl-3,5-dimethyl-oxazolidine-2,4-dione
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	US: D (Evidence of risk)
Pharmacokinetic data
Protein binding	Not significant
Identifiers
CAS Number	115-67-3
ATC code	N03AC01
PubChem	CID 8280
IUPHAR/BPS	7261
DrugBank	DB00617 Y
ChemSpider	7979 Y
UNII	Z615FRW64N Y
KEGG	D00495 Y
ChEMBL	CHEMBL1100 Y
Chemical data
Formula	C7H11NO3
Molar mass	157.167 g/mol
Chirality	1 : 1 mixture (racemate)
SMILES O=C1N(C(=O)OC1(C)CC)C
InChI InChI=1S/C7H11NO3/c1-4-7(2)5(9)8(3)6(10)11-7/h4H2,1-3H3 Y Key:VQASKUSHBVDKGU-UHFFFAOYSA-N Y
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Paramethadione is an anticonvulsant in the oxazolidinedione class. It is associated with fetal trimethadione syndrome, which is also known as paramethadione syndrome.^[1]

Chemistry

Paramethadione, 5-ethyl-3,5-dimethyloxazolidine-2,4-dione, differs from trimethadione only in the substitution of one methyl group with an ethyl group. It is synthesized in a completely analogous manner, except that it comes from 2-hydroxy-2-methylbutyric acid instead of 2-hydroxyisobutyric acid.

• M.A. Spielman, U.S. Patent 2,575,693 (1951).

References

External links

• DDB 33106

• Hoffman, D; Chun A (1975). "Paramethadione and metabolite serum levels in humans after a single oral paramethadione dose". J Pharm Sci 64 (10): 1702–1703. doi:10.1002/jps.2600641027. PMID 1185541.