Compound: MEPHENYTOIN
SMILES: O=C1N(C(=O)C(N1)(c2ccccc2)CC)C
InChIKey: GMHKMTDVRCWUDX-UHFFFAOYSA-N
Synonyms: MEPHENYTOIN, 50-12-4, Mesantoin, Methoin, Methylphenetoin, 5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione, Methyl hydantoin, Phenylethylmethylhydantoin, 3-Ethylnirvanol, Mephenytoinum, Mefenitoina, Mephenytoine, Mephenetoinum, 5-Ethyl-3-methyl-5-phenylhydantoin, 2,4-Imidazolidinedione, 5-ethyl-3-methyl-5-phenyl-, NSC-34652, 3-Methyl-5,5-phenylethylhydantoin, 3-Methyl-5-ethyl-5-phenylhydantoin, 5-Ethyl-3-methyl-5-phenylimidazolidin-2,4-dione, CHEBI:6757, DTXSID9023257, R420KW629U, NSC34652, Mefenetoin, Methyl Phenetoin, Phenetoin, Methyl, 4-ethyl-2-hydroxy-1-methyl-4-phenyl-4,5-dihydro-1H-imidazol-5-one, (+-)-Mephenytoin, 5 Ethyl 3 Methyl 5 Phenylhydantoin, RefChem:55581, DTXCID003257, N03AB04, 200-012-8, Phenantoin, Epiazin, Insulton, Sedantoin, Sedantoinal, Triantoin, Metydan, Sacerno, Mesontoin, mephentoin, (+/-)-Mephenytoin, rac-Mephenytoin, 5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione, Hydantoin, 5-ethyl-3-methyl-5-phenyl-, 5-Ethyl-5-fenyl-3-methylhydantoin, 5-Ethyl-3-methyl-5-phenyl-2,4(3H,5H)-imidazoledione, l-Mephenytoin, 3-Methyl-5,5-ethylphenylhydantoin, MFCD00022407, Mesdontoin, Gerot-epilan, Sedantional, (-)-5-Ethyl-3-methyl-5-phenylhydantoin, Mefenitoina [INN-Spanish], Mephenytoine [INN-French], Mephenytoinum [INN-Latin], 5-ethyl-3-methyl-5-phenyl-imidazolidine-2,4-dione, Mesantoin (TN), HSDB 3581, 5-Ethyl-5-fenyl-3-methylhydantoin [Czech], SR-05000001478, Mephenytoin (USP/INN), EINECS 200-012-8, NSC 34652, BRN 0017282, 50-12-4 (racemic), UNII-R420KW629U, (+-)-5-Ethyl-3-methyl-5-phenylhydantoin, ()-Mephenytoin, Mephenytoin [USAN:USP:INN:BAN], 3-Methyl-5, 5-ethylphenylhydantoin, l-3-Methyl-5-ethyl-5-phenylhydantoin, Mephenytoin (Standard), Mephenytoin Impurity 3, Spectrum_001494, MEPHENYTOIN [MI], Prestwick0_001108, Prestwick1_001108, Prestwick2_001108, Prestwick3_001108, Spectrum4_001094, MEPHENYTOIN [INN], ETHYLMETHYLHYDANTOIN, MEPHENYTOIN [HSDB], MEPHENYTOIN [USAN], CHEMBL861, Epitope ID:768766, MEPHENYTOIN [VANDF], MEPHENYTOIN [MART.], Oprea1_289074, SCHEMBL21766, BSPBio_001216, KBioGR_001508, KBioSS_001974, MEPHENYTOIN [WHO-DD], MLS002154157, DivK1c_000937, SPBio_003088, BPBio1_001338, GTPL7223, orb1306310, orb1306367, orb3141271, NIOSH/MU2276000, HMS502O19, HY-B1184R, KBio1_000937, KBio2_001974, KBio2_004542, KBio2_007110, (+/-)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione, MEPHENYTOIN [ORANGE BOOK], NINDS_000937, 2,4-Imidazolidinedione, 5-ethyl-3-methyl-5-phenyl-, (+-)-, GLXC-27003, HMS1571M18, HMS2089J22, HMS2098M18, HMS2230E21, HMS3369F15, HMS3715M18, MEPHENYTOIN [USP IMPURITY], 2, 5-ethyl-3-methyl-5-phenyl-, AAA05012, HY-B1184, Mephenytoin 1.0 mg/ml in Methanol, BDBM50103593, EBC-06030, EX-A15165, WLN: T5MVNV EHJ C1 E2 ER, AKOS015962176, CCG-213191, CS-4793, DB00532, IDI1_000937, NCGC00165924-01, NCGC00165924-02, AC-15964, AS-56694, DA-55346, SMR001233457, SY129591, DB-055496, (+/-)-5-Ethyl-3-methyl-5-phenylhydantoin, AB00052368, MU22760000, NS00008986, (.+/-.)-5-Ethyl-3-methyl-5-phenylhydantoin, BIM-0051837.0001, D00375, EN300-697588, AB00052368-07, AB00052368_08, Hydantoin, 5-ethyl-3-methyl-5-phenyl-, (-)-, 5-Ethyl-3-methyl-5-phenyl-2,5H)-imidazoledione, Q1175385, SR-05000001478-1, SR-05000001478-3, 2, 4-Imidazolidinedione, 5-ethyl-3-methyl-5-phenyl-, BRD-A83937277-001-03-0, BRD-A83937277-001-10-5, Z53843610, (S)-(+)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione, 2,4-IMIDAZOLIDINEDIONE, 5-ETHYL-3-METHYL-5-PHENYL-, (+/-)-
Theoretical properties:
molecular_formula: C12H14N2O2
molecular_weight: 218.25 g/mol
exact_mass: 218.105527694 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 16
topological_polar_surface_area: 49.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
Descriptions:
pubchem: Mephenytoin is 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. It has a role as an anticonvulsant.
chebi: 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.
chembl: MEPHENYTOIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Mephenytoin (marketed as Mesantoin by Novartis) 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.