General Information of Drug (ID: DR1025)
Drug Name
Mephenytoin
Synonyms
Mefenitoina; Mephenetoinum; Mephenytoine; Mephenytoinum; Mesantoin; Mesdontoin; Mesontoin; Methoin; Methyl hydantoin; Methylphenetoin; Metydan; Phenantoin; Phenylethylmethylhydantoin; Sacerno; Sedantional; Sedantoin; Sedantoinal; Triantoin; Epiazin; Epilan; Fenantoin; Gerot-epilan; Insulton; MEPHENYTOIN; mephentoin; (+/-)-Mephenytoin; (S)-Mephenytoin; 3-Ethylnirvanol; 3-Methyl-5,5-phenylethylhydantoin; 3-Methyl-5-ethyl-5-phenylhydantoin; 5-Ethyl-3-methyl-5-phenylhydantoin; 5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 218.25 Topological Polar Surface Area 49.4
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
4060
PubChem SID
92176 ; 220439 ; 4359670 ; 7847441 ; 7872066 ; 8150040 ; 8152547 ; 10524271 ; 11336112 ; 11361351 ; 11364388 ; 11366950 ; 11369512 ; 11374646 ; 11377674 ; 11462323 ; 11467136 ; 11468256 ; 11486824 ; 11492908 ; 11495308 ; 14773490 ; 29217682 ; 29223171 ; 46508677 ; 47291207 ; 47662362 ; 47959838 ; 47959839 ; 48035210 ; 48185062 ; 48416216 ; 49698809 ; 49703443 ; 49977224 ; 49977225 ; 50111722 ; 53789258 ; 56463168 ; 57322121 ; 79894519 ; 85788588 ; 92126062 ; 92308878 ; 92714624 ; 99302025 ; 103224438 ; 103914622 ; 104305314 ; 121363733
ChEBI ID
CHEBI:6757
CAS Number
50-12-4
TTD Drug ID
D07RGW
Formula
C12H14N2O2
Canonical SMILES
CCC1(C(=O)N(C(=O)N1)C)C2=CC=CC=C2
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)
InChIKey
GMHKMTDVRCWUDX-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
4'-hydroxymephenytoin DM018102 N. A. Oxidation - Hydroxylation 1 [9]
Nirvanol DM015360
1810905
Oxidation - Demethylation 1 [9] , [10]
Mephenytoin Metabolite M3 DM018103 N. A. Conjugation - Glucuronidation 2 [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009969 Mephenytoin 4'-hydroxymephenytoin Oxidation - Hydroxylation CYP2C19 [9]
MR009971 Mephenytoin Nirvanol Oxidation - Demethylation CYP2C9 ... [9], [10]
MR009970 4'-hydroxymephenytoin Mephenytoin Metabolite M3 Conjugation - Glucuronidation Unclear [9]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[5]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[7]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[7]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[8]
⏷ Show the Full List of 9  DME(s)
References
1 Mephenytoin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Comparison of (S)-mephenytoin and proguanil oxidation in vitro: contribution of several CYP isoforms. Br J Clin Pharmacol. 1999 Aug;48(2):158-67.
3 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
4 Cytochrome P450 metabolic dealkylation of nine N-nitrosodialkylamines by human liver microsomes. Carcinogenesis. 1996 Sep;17(9):2029-34.
5 Evidence that CYP2C19 is the major (S)-mephenytoin 4'-hydroxylase in humans. Biochemistry. 1994 Feb 22;33(7):1743-52.
6 Ethnic differences in genetic polymorphisms of CYP2D6, CYP2C19, CYP3As and MDR1/ABCB1. Drug Metab Pharmacokinet. 2004 Apr;19(2):83-95.
7 Species differences in stereoselective metabolism of mephenytoin by cytochrome P450 (CYP2C and CYP3A). J Pharmacol Exp Ther. 1993 Jan;264(1):89-94.
8 Cytochromes P450 mediating the N-demethylation of amitriptyline. Br J Clin Pharmacol. 1997 Feb;43(2):137-44.
9 Quantification of mephenytoin and its metabolites 4'-hydroxymephenytoin and nirvanol in human urine using a simple sample processing method
10 Relation of in vivo drug metabolism to stereoselective fetal hydantoin toxicology in mouse: evaluation of mephenytoin and its metabolite, nirvanol

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