Compound: phenytoin
SMILES: O=C1NC(=O)C(N1)(c2ccccc2)c3ccccc3
InChIKey: CXOFVDLJLONNDW-UHFFFAOYSA-N
Synonyms: phenytoin, 5,5-DIPHENYLHYDANTOIN, 57-41-0, Diphenylhydantoin, 5,5-diphenylimidazolidine-2,4-dione, Phenytoine, Zentropil, Lepitoin, Diphantoin, Dilabid, Epamin, Dihydantoin, Diphenylan, Dihycon, Sodanton, Diphedan, Fenitoina, Fenylepsin, Hidantal, Lehydan, Di-Hydan, Denyl, Eptal, Diphenylhydatanoin, Auranile, Dantinal, Dantoinal, Dantoine, Difetoin, Difhydan, Dilantine, Dillantin, Dintoina, Diphedal, Diphenin, Diphenine, Diphentyn, Ditoinate, Elepsindon, Enkelfel, Epifenyl, Epihydan, Epilantin, Fenytoine, Hidantilo, Hidantina, Hidantomin, Hydantal, Idantoil, Idantoin, Kessodanten, Phanantin, Phanatine, Phenatoine, Phentoin, Phentytoin, Ritmenal, Silantin, Sodantoin, Solantin, Sylantoic, Thilophenyl, Zentronal, Danten, Dintoin, Epelin, Epinat, Epised, Fentoin, Lepsin, Saceril, Sanepil, Hidan, Ekko, Ictalis simple, Toin unicelles, 5,5-Diphenyl-2,4-imidazolidinedione, Om-Hydantoine, Dantoinal klinos, Di-Lan, Di-Phetine, Epdantoine simple, Gerot-epilan-D, Hidantina vitoria, Comitoina, Epilan-D, Neosidantoina, Novantoina, Causoin, Hidantina senosian, Hydantol, Minetoin, Convul, Ekko capsules, Neos-Hidantoina, Om hidantoina simple, Phenytoinum, TOIN, 2,4-Imidazolidinedione, 5,5-diphenyl-, Dilantin-125, Diphentoin, Epanutin, Hydantin, Comital, Solantoin, Solantyl, 5,5-Dwufenylohydantoina, Eptoin, DILANTIN-30, Citrullamon, 5,5-Diphenylimidazolidin-2,4-dione, Hydantoin, 5,5-diphenyl-, 5,5-Diphenyl-imidazolidine-2,4-dione, NCI-C55765, CHEBI:8107, NSC-8722, DTXSID8020541, 6158TKW0C5, DTXCID60541, Fenitoin, 5,5-diphenyltetrahydro-1H-2,4-imidazoledione, SM-88 COMPONENT PHENYTOIN, Dilantin Infatabs, 5,5-di(phenyl)imidazolidine-2,4-dione, Phenytoin Infatabs, RefChem:861853, N03AB02, 200-328-6, Epilan, Fenantoin, Dilantin, Aleviatin, Hydantoinal, Difenin, Labopal, Oxylan, Dilantin acid, Phenhydanin, Sinergina, Sodanthon, Iphenylhydantoin, Phenytoin-Gerot, Difenilhidantoina, Fenytoin Dak, Didan TDC 250, Epdantoin Simple, Phenytoin AWD, Epilan D, Diphenat, Hindatal, Fenitoina [INN-Spanish], Phenytoine [INN-French], Phenytoinum [INN-Latin], Difenilhidantoina [Spanish], Diphenylhydantoine [French], Fenantoin Mn Pharma, Diphenylhydantoine, Di-Lan (VAN), Diphenylhydantoin (VAN), DPH (VAN), 5,5-diphenyl hydantoin, 5,5-Diphenylhydantoin (IUPAC), 5,5-Dwufenylohydantoina [Polish], CCRIS 515, MFCD00005264, AI3-52498, Dilantin (TN), Novophenytoin, MLS000069789, Citrulliamon, Phenitoin, Fenidantoin s, Epasmir 5, NCGC00021139-03, SMR000059026, Fenidantoin "s", 5,5-DIPHENYLHYDANTOIN-D5 98 ATOM % D, Epasmir "5", Didan-tdc-250, CAS-57-41-0, phenytoin (PHN), 5,5-diphenyl-1,3-diazolidine-2,4-dione, component of Mebroin, fenidantoin ''s'', epasmir ''5'', 5,5-Diphenylhydantoin (phenytoin), NSC 8722, EINECS 200-328-6, Phenythoin, UNII-6158TKW0C5, Phenantoin;, Fenantoin;, Fenytoine;, Phenhydan;, SR-01000075211, Epanutin;, Fenitoin;, Pyoredol;, Epsolin;, IFLab1_000214, Pentran;, Phenytoin RS, Phenytoin CRS, Fenidantoin 's', HSDB 3160, Di-Hydan;, Episar (Salt/Mix), Epasmir '5', Aladdin (Salt/Mix), Alepsin (Salt/Mix), Epsolin (Salt/Mix), Phenytoin (Lepitoin), Phenytoin (Standard), Tacosal (Salt/Mix), Phenytoin [USAN:USP:INN:BAN:JAN], Antisacer (Salt/Mix), Epdantoin (Salt/Mix), Epileptin (Salt/Mix), Hydantoin,5-diphenyl-, Spectrum_001105, Fenigramon (Salt/Mix), Citrullamon (Salt/Mix), Opera_ID_394, PHENYTOIN [INN], PHENYTOIN [JAN], 2, 5,5-diphenyl-, PHENYTOIN [MI], CHEMBL16, PHENYTOIN [HSDB], PHENYTOIN [IARC], PHENYTOIN [USAN], Spectrum2_001281, Spectrum3_000890, Spectrum4_000984, Spectrum5_001369, Lopac-D-4007, PHENYTOIN [VANDF], Epitope ID:117723, PHENYTOIN [MART.], D 4007, PHENYTOIN [USP-RS], PHENYTOIN [WHO-DD], PHENYTOIN [WHO-IP], SCHEMBL3440, BIDD:PXR0090, Lopac0_000329, Lopac0_000378, Oprea1_373280, BSPBio_001437, KBioGR_001387, KBioSS_001585, MLS001074087, MLS002454401, BIDD:GT0625, DivK1c_000507, Soluble phenytoin (Salt/Mix), SPBio_001281, Phenytoin (JP18/USP/INN), Phenytoin, 1mg/ml in Methanol, GTPL2624, orb1310151, orb3025200, PHENYTOIN [ORANGE BOOK], 2-hydroxy-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one, PHENYTOIN [EP MONOGRAPH], PHENYTOIN [USP IMPURITY], SCHEMBL11836878, HY-B0448R, KBio1_000507, KBio2_001585, KBio2_004153, KBio2_006721, KBio3_001780, PHENYTOIN [USP MONOGRAPH], WLN: T5MVMV EHJ ER& ER, 5,5-Diphenylhydantoin, >=99%, NINDS_000507, Phenytoin 1.0 mg/ml in Methanol, HMS1412J16, HMS1694O05, HMS1791H19, HMS1989H19, HMS2089E11, HMS2236J06, HMS3261K17, HMS3402H19, HMS3657O03, HMS5081O17, PHENYTOINUM [WHO-IP LATIN], SMSSF-0000406, HY-B0448, Hydantoin, 5,5-diphenyl- (8CI), MSK10317, Tox21_110861, Tox21_202299, Tox21_300281, Tox21_500378, AC-376, BDBM50003655, BDBM50101816, EBC-04217, Phenytoin for system suitability CRS, s2525, SBB057224, STK058029, STK182871, STL454130, PHENYTOIN COMPONENT OF SM-88, AKOS000416887, AKOS003245432, Tox21_110861_1, CCG-104011, CCG-221682, DB00252, FD22484, LP00378, Phenytoin 1000 microg/mL in Methanol, IDI1_000507, IDI1_008433, NCGC00015342-01, NCGC00015342-02, NCGC00015342-03, NCGC00015342-04, NCGC00015342-05, NCGC00015342-06, NCGC00015342-07, NCGC00015342-08, NCGC00015342-09, NCGC00015342-10, NCGC00015342-11, NCGC00015342-12, NCGC00021139-01, NCGC00021139-02, NCGC00021139-04, NCGC00021139-05, NCGC00021139-06, NCGC00021139-07, NCGC00021139-08, NCGC00021139-09, NCGC00021139-10, NCGC00021139-11, NCGC00091492-01, NCGC00091492-02, NCGC00091492-03, NCGC00091492-04, NCGC00091492-05, NCGC00093810-01, NCGC00093810-02, NCGC00254135-01, NCGC00259848-01, NCGC00261063-01, 5,5-?Diphenyl-?2,4-?imidazolidinedione, DA-56808, imidazolidine-2,4-dione, 5,5-diphenyl-, 5,5-Diphenyl-1H-imidazolidine-2,4-dione, D0894, EU-0100378, NS00010290, ST45024762, SW203757-2, EN300-16818, C07443, D00512, E76094, 2,4-Imidazolidinedione, 5,5-diphenyl- (9CI), AB00374253-10, AB00374253-11, AB00374253_13, F358172, Q410400, SR-01000003141, doi:10.14272/CXOFVDLJLONNDW-UHFFFAOYSA-N.1, SR-01000003141-8, SR-01000075211-2, BRD-K55930204-001-02-7, BRD-K55930204-001-20-9, BRD-K55930204-236-11-0, BRD-K55930204-236-23-5, BRD-K55930204-236-24-3, Z56786458, 4-hydroxy-5,5-diphenyl-1,5-dihydro-2H-imidazol-2-one, F0020-1370, F0081-0306, Phenytoin, European Pharmacopoeia (EP) Reference Standard, Phenytoin, United States Pharmacopeia (USP) Reference Standard, Phenytoin, Pharmaceutical Secondary Standard; Certified Reference Material, Phenytoin for system suitability, European Pharmacopoeia (EP) Reference Standard, InChI=1/C15H12N2O2/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,16,17,18,19
Theoretical properties:
molecular_formula: C15H12N2O2
molecular_weight: 252.27 g/mol
exact_mass: 252.089877630 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 19
topological_polar_surface_area: 58.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Needles (alcohol)
color: Needles (alcohol)
odor: Odorless
melting_point: 563 to 568 °F (NTP, 1992)
solubility: less than 0.1 mg/mL at 66 °F (NTP, 1992)
Descriptions:
pubchem: Diphenylhydantoin (Phenytoin) can cause cancer and developmental toxicity according to an independent committee of scientific and health experts.
chebi: A imidazolidine-2,4-dione that consists of hydantoin bearing two phenyl substituents at position 5.
chembl: PHENYTOIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Phenytoin (PHT), sold under the brand name Dilantin among others, is an anti-seizure medication. It is useful for the prevention of tonic-clonic seizures (also known as grand mal seizures) and focal seizures, but not absence seizures. The intravenous form, fosphenytoin, is used for status epilepticus that does not improve with benzodiazepines.  It may also be used for certain heart arrhythmias or neuropathic pain. It can be taken intravenously or by mouth. The intravenous form generally begins working within 30 minutes and is effective for roughly 24 hours. Blood levels can be measured to determine the proper dose.
Common side effects include nausea, stomach pain, loss of appetite, poor coordination, increased hair growth, and enlargement of the gums. Potentially serious side effects include sleepiness, self harm, liver problems, bone marrow suppression, low blood pressure, toxic epidermal necrolysis, and atrophy of the cerebellum. There is evidence that use during pregnancy results in abnormalities in the baby.  It appears to be safe to use when breastfeeding. Alcohol may interfere with the medication's effects.
Phenytoin was first made in 1908 by the German chemist Heinrich Biltz and found useful for seizures in 1936. It is on the World Health Organization's List of Essential Medicines. Phenytoin is available as a generic medication.  In 2020, it was the 260th most commonly prescribed medication in the United States, with more than 1 million prescriptions.