Structure via PubChem · Public domain (PubChem)
mephenytoin
Sign in to saveAlso known as MES204, Mesantoin®
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.
Chemical data
- Formula
- C12H14N2O2
- Molecular weight
- 218.25 g/mol
- IUPAC name
- 5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
- SMILES
- CCC1(C(=O)N(C(=O)N1)C)C2=CC=CC=C2
- InChIKey
- GMHKMTDVRCWUDX-UHFFFAOYSA-N
- XLogP
- 1.5
- Polar surface area
- 49.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1946
- Admin. routes
- oral
- Indications
- epilepsy
via ChEMBL · EBI
Research
1,086 papers- Mephenytoin: a reappraisal.Epilepsia · 1976
- Genetic polymorphism of mephenytoin metabolism.Progress in clinical and biological research · 1986
- Hydroxylation polymorphisms of debrisoquine and mephenytoin in European populations.European journal of clinical pharmacology · 1990
- Polymorphism in stereoselective hydroxylations of mephenytoin and hexobarbital by Japanese liver samples in relation to cytochrome P-450 human-2 (IIC9).Xenobiotica; the fate of foreign compounds in biological systems · 1992
- Mephenytoin and sparteine pharmacogenetics in Canadian Caucasians.Clinical pharmacology and therapeutics · 1984
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 218.106
- Has use
- medication
Show 6 more facts
- chemical formula
- C₁₂H₁₄N₂O₂
- medical condition treated
- temporal lobe epilepsy
- canonical SMILES
- CCC1(C(=O)N(C(=O)N1)C)C2=CC=CC=C2
- defined daily dose
- 0.4
- subject has role
- anticonvulsant agent
- Commons category
- Mephenytoin
Sources (6)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
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.
Excerpted from Wikipedia’s “mephenytoin” article, available under the CC BY-SA 4.0 licence.