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MedKoo Cat#: 318188 | Name: Mephenytoin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mephenytoin (racemic) 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.

Chemical Structure

Mephenytoin
Mephenytoin
CAS#50-12-4 (racemic)

Theoretical Analysis

MedKoo Cat#: 318188

Name: Mephenytoin

CAS#: 50-12-4 (racemic)

Chemical Formula: C12H14N2O2

Exact Mass: 218.1055

Molecular Weight: 218.25

Elemental Analysis: C, 66.04; H, 6.47; N, 12.84; O, 14.66

Price and Availability

Size Price Availability Quantity
10mg USD 90.00 Ready to ship
25mg USD 150.00 Ready to ship
50mg USD 250.00 Ready to ship
100mg USD 450.00 Ready to ship
200mg USD 750.00 Ready to ship
1g USD 2,650.00 Ready to ship
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Related CAS #
70989-04-7 (s-isomer) 50-12-4 (racemic)
Synonym
Mephenytoin; Methoin; Mesantoin; Phenantoin; Methylphenetoin; Insulton.
IUPAC/Chemical Name
5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
InChi Key
GMHKMTDVRCWUDX-UHFFFAOYSA-N
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)
SMILES Code
CCC1(C(=O)N(C(=O)N1)C)C2=CC=CC=C2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 218.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Vijayabhaskar V, Srivastava P, Rajagopal S. Breaking the sensitivity limitations of cytochrome P450 oxidation product: dansyl chloride derivatisation of 4-OH mephenytoin, a CYP2C19 metabolite and its application to in vitro CYP inhibition assay. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 May 1;989:27-36. doi: 10.1016/j.jchromb.2015.02.031. Epub 2015 Mar 1. PubMed PMID: 25797720. 2: Wang H, An N, Wang H, Gao Y, Liu D, Bian T, Zhu J, Chen C. Evaluation of the effects of 20 nonsynonymous single nucleotide polymorphisms of CYP2C19 on S-mephenytoin 4'-hydroxylation and omeprazole 5'-hydroxylation. Drug Metab Dispos. 2011 May;39(5):830-7. doi: 10.1124/dmd.110.037549. Epub 2011 Feb 16. PubMed PMID: 21325430. 3: Lee SJ, Kim WY, Kim H, Shon JH, Lee SS, Shin JG. Identification of new CYP2C19 variants exhibiting decreased enzyme activity in the metabolism of S-mephenytoin and omeprazole. Drug Metab Dispos. 2009 Nov;37(11):2262-9. doi: 10.1124/dmd.109.028175. Epub 2009 Aug 6. PubMed PMID: 19661214. 4: Klaassen T, Jetter A, Tomalik-Scharte D, Kasel D, Kirchheiner J, Jaehde U, Fuhr U. Assessment of urinary mephenytoin metrics to phenotype for CYP2C19 and CYP2B6 activity. Eur J Clin Pharmacol. 2008 Apr;64(4):387-98. Epub 2007 Dec 11. PubMed PMID: 18071681. 5: Crespi CL, Chang TK, Waxman DJ. CYP2C19-mediated (S)-mephenytoin 4'-hydroxylation assayed by high-performance liquid chromatography with radiometric detection. Methods Mol Biol. 2006;320:115-9. PubMed PMID: 16719381. 6: Klaassen T, Kasel D, Harlfinger S, Fuhr U. Quantification of mephenytoin and its metabolites 4'-hydroxymephenytoin and nirvanol in human urine using a simple sample processing method. Rapid Commun Mass Spectrom. 2004;18(15):1675-80. PubMed PMID: 15282764. 7: Wang H, Nie YQ, Dai SJ, She QZ, Li YY. [The effect of proton pump inhibitor on intragastric acidity and it relation to S-mephenytoin hydroxylase genetic polymorphism]. Zhonghua Nei Ke Za Zhi. 2003 Nov;42(11):777-80. Chinese. PubMed PMID: 14636465. 8: Prost F, Thormann W. Capillary electrophoresis to assess drug metabolism induced in vitro using single CYP450 enzymes (Supersomes): application to the chiral metabolism of mephenytoin and methadone. Electrophoresis. 2003 Aug;24(15):2577-87. PubMed PMID: 12900870. 9: Jansson B, Simonsson US, Ashton M. Simultaneous enantiospecific separation and quantitation of mephenytoin and its metabolites nirvanol and 4'-hydroxymephenytoin in human plasma by liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 5;791(1-2):179-91. PubMed PMID: 12798178. 10: He N, Yan FX, Huang SL, Wang W, Xiao ZS, Liu ZQ, Zhou HH. CYP2C19 genotype and S-mephenytoin 4'-hydroxylation phenotype in a Chinese Dai population. Eur J Clin Pharmacol. 2002 Apr;58(1):15-8. Epub 2002 Feb 22. PubMed PMID: 11956668. 11: Zhou HH. CYP2C19 genotype determines enzyme activity and inducibility of S-mephenytoin hydroxylase. Clin Chim Acta. 2001 Nov;313(1-2):203-8. Review. PubMed PMID: 11694260. 12: Eap CB, Bondolfi G, Zullino D, Bryois C, Fuciec M, Savary L, Jonzier-Perey M, Baumann P. Pharmacokinetic drug interaction potential of risperidone with cytochrome p450 isozymes as assessed by the dextromethorphan, the caffeine, and the mephenytoin test. Ther Drug Monit. 2001 Jun;23(3):228-31. PubMed PMID: 11360030. 13: Hadama A, Ieiri I, Morita T, Kimura M, Urae A, Irie S, Kaneda T, Mamiya K, Tashiro N, Higuchi S, Otsubo K. P-hydroxylation of phenobarbital: relationship to (S)-mephenytoin hydroxylation (CYP2C19) polymorphism. Ther Drug Monit. 2001 Apr;23(2):115-8. PubMed PMID: 11294510. 14: Yao TW, Zeng S, Wang TW, Chen SQ. Phenotype analysis of cytochrome P450 2C19 in Chinese subjects with mephenytoin S/R enantiomeric ratio in urine measured by chiral GC. Biomed Chromatogr. 2001 Feb;15(1):9-13. PubMed PMID: 11180294. 15: Laine K, Tybring G, Bertilsson L. No sex-related differences but significant inhibition by oral contraceptives of CYP2C19 activity as measured by the probe drugs mephenytoin and omeprazole in healthy Swedish white subjects. Clin Pharmacol Ther. 2000 Aug;68(2):151-9. PubMed PMID: 10976546. 16: Xie HG, Kim RB, Stein CM, Wilkinson GR, Wood AJ. Genetic polymorphism of (S)-mephenytoin 4'-hydroxylation in populations of African descent. Br J Clin Pharmacol. 1999 Sep;48(3):402-8. Erratum in: Br J Clin Pharmacol 2001 Sep;52(3):343. PubMed PMID: 10510153; PubMed Central PMCID: PMC2014331. 17: Coller JK, Somogyi AA, Bochner F. Comparison of (S)-mephenytoin and proguanil oxidation in vitro: contribution of several CYP isoforms. Br J Clin Pharmacol. 1999 Aug;48(2):158-67. PubMed PMID: 10417492; PubMed Central PMCID: PMC2014289. 18: Herrlin K, Massele AY, Jande M, Alm C, Tybring G, Abdi YA, Wennerholm A, Johansson I, Dahl ML, Bertilsson L, Gustafsson LL. Bantu Tanzanians have a decreased capacity to metabolize omeprazole and mephenytoin in relation to their CYP2C19 genotype. Clin Pharmacol Ther. 1998 Oct;64(4):391-401. PubMed PMID: 9797796. 19: Ibeanu GC, Goldstein JA, Meyer U, Benhamou S, Bouchardy C, Dayer P, Ghanayem BI, Blaisdell J. Identification of new human CYP2C19 alleles (CYP2C19*6 and CYP2C19*2B) in a Caucasian poor metabolizer of mephenytoin. J Pharmacol Exp Ther. 1998 Sep;286(3):1490-5. PubMed PMID: 9732415. 20: Feng HJ, Huang SL, Wang W, Zhou HH. The induction effect of rifampicin on activity of mephenytoin 4'-hydroxylase related to M1 mutation of CYP2C19 and gene dose. Br J Clin Pharmacol. 1998 Jan;45(1):27-9. PubMed PMID: 9489590; PubMed Central PMCID: PMC1873992.