Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:42 UTC |
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HMDB ID | HMDB0014673 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Mephenytoin |
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Description | Mephenytoin, also known as mefenitoina or methylphenetoin, belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. Mephenytoin is a drug which is used for the treatment of refractory partial epilepsy. In humans, mephenytoin is involved in the ibuprofen action pathway. Mephenytoin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Mephenytoin. |
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Structure | CCC1(NC(=O)N(C)C1=O)C1=CC=CC=C1 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) |
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Synonyms | Value | Source |
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DL-Mephenytoin | ChEBI | Mefenitoina | ChEBI | Mephenytoine | ChEBI | Mephenytoinum | ChEBI | Methylphenetoin | ChEBI | Phenylethylmethylhydantoin | ChEBI | Mesantoin | Kegg | Mephentoin | HMDB | Methyl hydantoin | HMDB | 5 Ethyl 3 methyl 5 phenylhydantoin | MeSH, HMDB | 5-Ethyl-3-methyl-5-phenylhydantoin | MeSH, HMDB | Phenetoin, methyl | MeSH, HMDB | Methoin | MeSH, HMDB | Methyl phenetoin | MeSH, HMDB | Phenantoin | MeSH, HMDB | Mefenetoin | MeSH, HMDB |
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Chemical Formula | C12H14N2O2 |
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Average Molecular Weight | 218.2518 |
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Monoisotopic Molecular Weight | 218.105527702 |
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IUPAC Name | 5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione |
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Traditional Name | mephenytoin |
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CAS Registry Number | 50-12-4 |
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SMILES | CCC1(NC(=O)N(C)C1=O)C1=CC=CC=C1 |
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InChI Identifier | 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) |
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InChI Key | GMHKMTDVRCWUDX-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Azolidines |
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Sub Class | Imidazolidines |
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Direct Parent | Phenylhydantoins |
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Alternative Parents | |
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Substituents | - 5-phenylhydantoin
- Phenylimidazolidine
- Alpha-amino acid or derivatives
- N-acyl urea
- Ureide
- Monocyclic benzene moiety
- Benzenoid
- Dicarboximide
- Urea
- Carbonic acid derivative
- Carboxylic acid derivative
- Azacycle
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic nitrogen compound
- Carbonyl group
- Organic oxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 135 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.97 g/L | Not Available | LogP | 1.3 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Mephenytoin,1TMS,isomer #1 | CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C | 1868.6 | Semi standard non polar | 33892256 | Mephenytoin,1TMS,isomer #1 | CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C | 1892.9 | Standard non polar | 33892256 | Mephenytoin,1TMS,isomer #1 | CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C | 2461.0 | Standard polar | 33892256 | Mephenytoin,1TBDMS,isomer #1 | CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C | 2094.5 | Semi standard non polar | 33892256 | Mephenytoin,1TBDMS,isomer #1 | CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C | 2133.2 | Standard non polar | 33892256 | Mephenytoin,1TBDMS,isomer #1 | CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C | 2531.4 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Mephenytoin EI-B (Non-derivatized) | splash10-0f79-2900000000-af8712fc36e2b911e9a8 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Mephenytoin EI-B (Non-derivatized) | splash10-0f79-2900000000-af8712fc36e2b911e9a8 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mephenytoin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ue9-1900000000-76ba03e4694ef29def3b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mephenytoin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mephenytoin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mephenytoin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Mephenytoin LC-ESI-qTof , Positive-QTOF | splash10-0159-3901000000-d726d8591f6fd6b87a0a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Mephenytoin , positive-QTOF | splash10-0159-3901000000-d726d8591f6fd6b87a0a | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mephenytoin 10V, Positive-QTOF | splash10-014i-0490000000-8c8bcd12840df6ae00f2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mephenytoin 20V, Positive-QTOF | splash10-001i-0920000000-360996524b6c1cdc8fe3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mephenytoin 40V, Positive-QTOF | splash10-0ue9-6900000000-5f6a566d2e8972a3e79c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mephenytoin 10V, Negative-QTOF | splash10-014i-0290000000-de9e2d95bc7cf0aea9ac | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mephenytoin 20V, Negative-QTOF | splash10-014i-7590000000-9cb9accf3f7737fa1483 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mephenytoin 40V, Negative-QTOF | splash10-000x-9600000000-a00ec47fefbdc60a200a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mephenytoin 10V, Positive-QTOF | splash10-014i-0190000000-8b9cb11606c241146d8b | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mephenytoin 20V, Positive-QTOF | splash10-00lr-1900000000-a867b49304e4c2814177 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mephenytoin 40V, Positive-QTOF | splash10-014i-6900000000-2fd710ba16d058127ae9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mephenytoin 10V, Negative-QTOF | splash10-014i-0090000000-4f94e1f66d72d6972b8a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mephenytoin 20V, Negative-QTOF | splash10-000i-2900000000-be298ddea23898cbfbc6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mephenytoin 40V, Negative-QTOF | splash10-01ox-6900000000-8676a25532452b4ac29b | 2021-09-24 | Wishart Lab | View Spectrum |
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