Misplaced Pages

Revision as of 18:31, 7 November 2011

Mephenytoin

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a611020
Routes of administration	Oral
ATC code	N03AB04 (WHO)
Pharmacokinetic data
Elimination half-life	7 hours
Identifiers
IUPAC name 5-ethyl-3-methyl-5-phenyl-imidazolidine-2,4-dione
CAS Number	50-12-4
PubChem CID	4060
DrugBank	DB00532
ChemSpider	3920
UNII	R420KW629U
KEGG	D00375
ChEMBL	ChEMBL861
CompTox Dashboard (EPA)	DTXSID9023257
ECHA InfoCard	100.000.012
Chemical and physical data
Formula	C12H14N2O2
Molar mass	218.252 g·mol
3D model (JSmol)	Interactive image
SMILES O=C2N(C(=O)NC2(c1ccccc1)CC)C
InChI InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16) Key:GMHKMTDVRCWUDX-UHFFFAOYSA-N
(verify)

Mephenytoin (marketed as Mesantoin by Novartis) is a hydantoin, used as an anticonvulsant. It was introduced approximately 10 years after phenytoin, in the late 1940s. The significant metabolite of mephenytoin is nirvanol (5-ethyl-5-phenylhydantoin), which was the first hydantoin (briefly used as a hypnotic). However, nirvanol is quite toxic and mephenytoin was only considered after other less toxic anticonvulsants had failed. It can cause potentially fatal blood dyscrasia in 1% of patients.

Mephenytoin is no longer available in the US or the UK. It is still studied largely because of its interesting hydroxylation polymorphism.

References

• The Treatment of Epilepsy edited by S. D. Shorvon, David R. Fish, Emilio Perucca, W. Edwin Dodson. Blackwell Publishing. 2004. ISBN 0-632-06046-8
• The Medical Treatment of Epilepsy by Stanley R Resor. Published by Marcel Dekker (1991). ISBN 0-8247-8549-5.
• The Comparative Toxicogenomics Database: Mephenytoin

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

• v
• t
• e

• Anticonvulsants
• Hydantoins
• Anticonvulsant stubs