An enantiomer of mephenytoin
Related Products
Active Metabolite(s)
21733Nirvanol
Enantiomer(s)
11913(S)-Mephenytoin
Metabolite(s)
16124(±)4-Hydroxymephenytoin
Technical Support & Resources

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Product Categories

Product Type

Biochemicals

Research Area

Xenobiotic Metabolism
Cytochrome P450s
CYP2C9
CYP2C19

(R)-Mephenytoin

Item No. 25891

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5R)-5-ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione
CAS Number
71140-51-7
Synonyms
  • (–)-Mephenytoin
  • (R)-5-ethyl-3-methyl-5-Phenylhydantoin
Molecular Formula
C12H14N2O2
Formula Weight
218.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 15 mg/ml
SMILES
O=C1[C@@](CC)(C2=CC=CC=C2)NC(N1C)=O
InChi Code
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)/t12-/m1/s1
InChi Key
GMHKMTDVRCWUDX-GFCCVEGCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Product Description

    (R)-Mephenytoin is the (R) enantiomer of the anticonvulsant mephenytoin.1 (R)-Mephenytoin can be demethylated by the cytochrome P450 (CYP) isoform CYP2C9 to form the active metabolite 5-ethyl-5-phenylhydantoin (nirvanol).2,3 The ratio of (S)-mephenytoin (Item No. 11913) to (R)-mephenytoin in urine following administration of the racemic mixture has been used to detect polymorphisms in drug metabolism by CYP2C19, as only (S)-mephenytoin is a substrate of CYP2C19.4,5,2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Meier, U.T., Kronbach, T., and Meyer, U.A. Assay of mephenytoin metabolism in human liver microsomes by high-performance liquid chromatography. Anal. Biochem. 151(2), 286-291 (1985).

    2. Lewis, D.F., Dickins, M., Weaver, R.J., et al. Molecular modelling of human CYP2C subfamily enzymes CYP2C9 and CYP2C19: Rationalization of substrate specificity and site-directed mutagenesis experiments in the CYP2C subfamily. Xenobiotica. 28(3), 235-268 (1998).

    3. Wong, P.T.H., Tan, S.F., and Lee, H.S. N-demethylation of methyl and dimethyl derivatives of phenytoin and their anticonvulsant activities in mice. Jpn. J. Pharmacol. 48(4), 473-478 (1988).

    4. Ferguson, R.J., de Morais, S.M., Benhamou, S., et al. A new genetic defect in human CYP2C19: Mutation of the initiation codon is responsible for poor metabolism of S-mephenytoin. J. Pharmacol. Exp. Ther. 284(1), 356-361 (1998).

    5. Guttendorf, R.J., Britto, M., Blouin, R.A., et al. Rapid screening for polymorphisms in dextromethorphan and mephenytoin metabolism. Br. J. Clin. Pharmacol. 29(4), 373-380 (1990).