A substrate of CYP2C19
Related Products
Active Metabolite(s)
21733Nirvanol
Enantiomer(s)
25891(R)-Mephenytoin
Metabolite(s)
16124(±)4-Hydroxymephenytoin
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

(S)-Mephenytoin

Item No. 11913

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5S)-5-ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione
CAS Number
70989-04-7
Synonyms
  • (+)-Mephenytoin
  • (S)-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@@](C2=CC=CC=C2)(CC)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-/m0/s1
InChi Key
GMHKMTDVRCWUDX-LBPRGKRZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $47

    Add

    5 mg

    $116

    Add

    10 mg

    $208

    Add

    25 mg

    $462

    Add
    Product Description

    (S)-Mephenytoin is a substrate of the cytochrome P450 (CYP) isoform CYP2C19, also known as mephenytoin 4-hydroxylase.1 CYP2C19 metabolizes a variety of therapeutic agents, including omeprazole, proguanil, diazepam, propranolol, citalopram, imipramine, and certain barbiturates.2 Genetic defects in CYP2C19 result in poor metabolism of these compounds, and (S)-mephenytoin can be used to screen for such mutations by assaying its metabolites in urine.2,3,4 (S)-Mephenytoin has anticonvulsant activities.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shimada, T., Misono, K.S., and Guengerich, F.P. Human liver microsomal cytochrome P-450 mephenytoin 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. The Journal of Biological Chemisty 261(2), 909-921 (1986).

    2. 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).

    3. Ozawa, S., Soyama, A., Saeki, M., et al. Ethnic differences in genetic polymorphisms of CYP2D6, CYP2C19, CYP3As and MDR1/ABCB1. Drug Metab. Pharmacokinet. 19(2), 83-95 (2004).

    4. 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).

    5. 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).

    Product Citations

    Negoro, R., Tasaka, M., Deguchi, S., et al. Generation of HepG2 cells with high expression of multiple drug-metabolizing enzymes for drug discovery research using a PITCh system. Cells 11(10), 1677 (2022).