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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:mephenytoin
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Accession:CHEBI:6757 term browser browse the term
Definition:An imidazolidine-2,4-dione (hydantoin) in which the imidazolidine nucleus carries a methyl group at N-3 and has ethyl and phenyl substituents at C-5. An anticonvulsant, it is no longer available in the USA or the UK but is still studied largely because of its interesting hydroxylation polymorphism.
Synonyms:exact_synonym: 5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
 related_synonym: DL-Mephenytoin;   Formula=C12H14N2O2;   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;   SMILES=CCC1(C(=O)N(C(=O)N1)C)C2=CC=CC=C2;   mefenitoina;   mephenytoine;   mephenytoinum;   methylphenetoin;   phenylethylmethylhydantoin
 alt_id: CHEBI:91914
 xref: CAS:50-12-4;   Drug_Central:1695;   KEGG:D00375;   LINCS:LSM-1852
 xref_mesh: MESH:D008617
 xref: PMID:11422005;   PMID:15282764;   PMID:25797720;   PMID:29438107;   Reaxys:17282;   Wikipedia:Mephenytoin


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mephenytoin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 decreases activity ISO Mephenytoin results in decreased activity of CYP1B1 protein CTD PMID:18420780 NCBI chr 6:2,308,179...2,316,739
Ensembl chr 6:2,307,808...2,316,722
JBrowse link
G Cyp2b1 cytochrome P450, family 2, subfamily b, polypeptide 1 decreases activity ISO Mephenytoin results in decreased activity of CYP2B10 protein CTD PMID:18420780 NCBI chr 7:99,142,431...99,183,540
Ensembl chr 7:99,142,450...99,181,783
JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 decreases methylation
increases metabolic processing
multiple interactions
decreases activity
ISO CYP2B6 protein results in decreased methylation of Mephenytoin
CYP2B6 protein results in increased metabolism of Mephenytoin
Mephenytoin inhibits the reaction [[isoimperatorin co-treated with NADP] results in decreased activity of CYP2B6 protein]; Mephenytoin inhibits the reaction [CYP2B6 protein results in decreased ethylation of 7-ethoxy-4-trifluoromethylcoumarin]; Mephenytoin inhibits the reaction [CYP2B6 protein results in increased chemical synthesis of 7-hydroxy-4-trifluoromethylcoumarin]
Mephenytoin results in decreased activity of CYP2B6 protein
CTD PMID:9241656 PMID:12433797 PMID:12464242 PMID:25500267 NCBI chr 1:83,163,103...83,236,615
Ensembl chr 1:83,163,079...83,236,615
JBrowse link
G Cyp2c6v1 cytochrome P450, family 2, subfamily C, polypeptide 6, variant 1 multiple interactions
increases metabolic processing
increases oxidation
affects hydroxylation
affects metabolic processing
increases hydroxylation
decreases activity
ISO 4-amino-2-phenoxymethanesulfonanilide inhibits the reaction [CYP2C19 protein results in increased oxidation of Mephenytoin]; [CYP2C19 protein results in increased metabolism of Mephenytoin] which results in increased chemical synthesis of 4-hydroxymephenytoin; [Mephenytoin results in decreased activity of CYP2C19 protein] which results in decreased degradation of vanoxerine; Fluoxetine inhibits the reaction [CYP2C19 protein results in increased hydroxylation of Mephenytoin]; Fluoxetine inhibits the reaction [CYP2C19 protein results in increased metabolism of Mephenytoin]; GH1 protein inhibits the reaction [CYP2C19 protein results in increased metabolism of Mephenytoin]; Lansoprazole inhibits the reaction [CYP2C19 protein results in increased hydroxylation of Mephenytoin]; Mephenytoin inhibits the reaction [CYP2C19 protein results in increased metabolism of 4,5-dihydropyrazole-1,5-dicarboxylic acid 1-((4-chlorophenyl)-amide) 5-(2-oxo-2H-(1,3')bipyridinyl-6'-yl)-amide]; Omeprazole inhibits the reaction [CYP2C19 protein results in increased hydroxylation of Mephenytoin]; Omeprazole inhibits the reaction [CYP2C19 protein results in increased metabolism of Mephenytoin]; Pantoprazole inhibits the reaction [CYP2C19 protein results in increased hydroxylation of Mephenytoin]; perfluorooctane sulfonic acid inhibits the reaction [CYP2C19 protein results in increased oxidation of Mephenytoin]; rabeprazole-thioether inhibits the reaction [CYP2C19 protein results in increased hydroxylation of Mephenytoin]; Resveratrol inhibits the reaction [CYP2C19 protein results in increased metabolism of Mephenytoin]; sitaxsentan inhibits the reaction [CYP2C19 protein results in increased metabolism of Mephenytoin]; Ticlopidine inhibits the reaction [CYP2C19 protein results in increased hydroxylation of Mephenytoin]; Ticlopidine inhibits the reaction [CYP2C19 protein results in increased metabolism of Mephenytoin]; Tranylcypromine inhibits the reaction [CYP2C19 protein results in increased metabolism of Mephenytoin]; ursolic acid inhibits the reaction [CYP2C19 protein results in increased metabolism of Mephenytoin]; zafirlukast inhibits the reaction [CYP2C19 protein results in increased metabolism of Mephenytoin]
CYP2C19 gene SNP affects the hydroxylation of Mephenytoin; CYP2C19 protein affects the hydroxylation of Mephenytoin
CYP2C19 protein affects the metabolism of Mephenytoin
CTD PMID:3577206 PMID:9170147 PMID:11502731 PMID:11907490 PMID:12401345 PMID:12433797 PMID:12464242 PMID:12467917 PMID:12569440 PMID:12637241 PMID:15043991 PMID:15155557 PMID:15258107 PMID:15370959 PMID:15618748 PMID:15860655 PMID:16049126 PMID:16124035 PMID:17267297 PMID:17418993 PMID:17478480 PMID:18979093 PMID:19053182 PMID:19697924 PMID:21915887 PMID:21964418 PMID:22652334 PMID:23721565 PMID:23850985 PMID:25084468 PMID:28119166 PMID:28762043 PMID:29445054 NCBI chr 1:147,713,879...147,814,410
Ensembl chr 1:147,713,892...147,888,007
JBrowse link
G Cyp2c79 cytochrome P450, family 2, subfamily c, polypeptide 79 decreases activity ISO Mephenytoin results in decreased activity of CYP2C29 protein CTD PMID:18420780 NCBI chr 1:147,236,480...147,307,988 JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 decreases activity ISO Mephenytoin results in decreased activity of CYP2E1 protein CTD PMID:18420780 NCBI chr 1:213,511,892...213,522,195
Ensembl chr 1:213,511,874...213,535,542
JBrowse link
G Gh1 growth hormone 1 multiple interactions ISO GH1 protein inhibits the reaction [CYP2C19 protein results in increased metabolism of Mephenytoin] CTD PMID:11907490 NCBI chr10:94,486,204...94,488,181
Ensembl chr10:94,486,205...94,488,180
JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 multiple interactions ISO Mephenytoin binds to and results in increased activity of NR1I2 protein CTD PMID:15039302 NCBI chr11:65,022,100...65,058,546
Ensembl chr11:65,022,100...65,058,545
JBrowse link

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                anticonvulsant 15171
                  mephenytoin 8
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                                    diazolidine 588
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                                        imidazolidinone 479
                                          imidazolidine-2,4-dione 458
                                            mephenytoin 8
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