Drug Information

General Information
Drug ID
DR00431
Drug Name
Phenytoin
Synonyms
2,4-Imidazolidinedione, 5,5-diphenyl-(9CI); 2-hydroxy-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one; 5,5-DIPHENYLHYDANTOIN; 5,5-Diphenyl-2,4-imidazolidinedione; 5,5-Diphenyl-imidazolidine-2,4-dione; 5,5-Diphenylhydantoin (IUPAC); 5,5-Diphenylhydantoin (phenytoin); 5,5-Diphenylimidazolidin-2,4-dione; 5,5-Dwufenylohydantoina; 5,5-Dwufenylohydantoina [Polish]; 5,5-diphenylimidazolidine-2,4-dione; Aleviatin; Antisacer; Auranile; CL12003; Causoin; Citrullamon; Citrulliamon; Comital; Comitoina; Component of Mebroin; Convul; D 4007; D4007_SIGMA; DILANTIN-30; DPH (VAN); Danten; Dantinal; Dantoinal; Dantoinal klinos; Dantoine; Denyl; Di-Hydan; Di-Lan; Di-Lan (VAN); Di-Phetine; Didan TDC 250; Didan-tdc-250; Difenilhidantoina; Difenilhidantoina [Spanish]; Difenin; Difetoin; Difhydan; Dihycon; Dihydan toin; Dihydantoin; Dilabid; Dilantin; Dilantin (TN); Dilantin Infatabs (TN); Dilantin Kapseals (TN); Dilantin acid; Dilantin-125; Dilantine; Dillantin; Dintoin; Dintoina; Diphantoin; Diphedal; Diphedan; Diphenat; Diphenin; Diphenine; Diphentoin; Diphentyn; Diphenylan; Diphenylhydantoin; Diphenylhydantoin (VAN); Diphenylhydantoine; Diphenylhydantoine [French]; Diphenylhydatanoin; Ditoinate; Ekko; Ekko capsules; Elepsi ndon; Elepsindon; Enkelfel; Epamin; Epanutin; Epanutin (TN); Epasmir (5); Epasmir 5; Epdantoin Simple; Epdantoine simple; Epelin; Epifenyl; Epihydan; Epilan D; Epilan-D; Epilantin; Epinat; Epised; Eptal; Eptoin; Eptoin (TN); Extended Phenytoin Sodium; Fen toin; Fenantoin Mn Pharma; Fenidantoin (s); Fenidantoin s; Fenitoin; Fenitoina; Fenitoina [INN-Spanish]; Fentoin; Fenylepsin; Fenytoin Dak; Fenytoine; Gerot-epilan-D; Hidan; Hidantal; Hidantilo; Hidantina; Hidantina senosian; Hidantina vitoria; Hidantomin; Hindatal; Hydantal; Hydantin; Hydantoin, 5,5-diphenyl-(8CI); Hydantoinal; Hydantol; IFLab1_000214; Ictalis simp le; Ictalis simple; Idantoil; Idantoin; Iphenylhydantoin; Kessodanten; Labopal; Lehydan; Lepitoin; Lepsin; Minetoin; Neos-Hidantoina; Neosidantoina; Novantoina; Novophenytoin; Om hidantoina simple; Om-Hydantoine; Oxylan; PHENYTEK; PHENYTOIN (5,5-DIPHENYLHYDANTOIN); PHENYTOIN SODIUM, EXTENDED; Phanantin; Phanatine; Phenat ine; Phenatine; Phenatoine; Phenhydan; Phenhydanin; Phenitoin; Phentoin; Phentytoin; Phenytek (TN); Phenytex; Phenytoin (JP15/USP/INN); Phenytoin (PHN); Phenytoin AWD; Phenytoin [USAN:INN:BAN:JAN]; Phenytoin-Gerot; Phenytoine; Phenytoine [INN-French]; Phenytoinum; Phenytoinum [INN-Latin]; Ritmenal; Saceril; Sanepil; Silantin; Sinergina; Sodanthon; Sodantoin; Sodanton; Sodium Diphenylhydantoinate; Solantin; Solantoin; Solantyl; Sylantoic;TOIN; Taco sal; Tacosal; Thilophenyl; Toin unicelles; Zentronal; Zentropil
Drug Type
Small molecular drug
Indication Seizures following neurosurgery [ICD11:8A6Z] Approved [1]
Therapeutic Class
Anticonvulsants
Structure
3D MOL 2D MOL
Formula
C15H12N2O2
Canonical SMILES
C1=CC=C(C=C1)C2(C(=O)NC(=O)N2)C3=CC=CC=C3
InChI
InChI=1S/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)
InChIKey
CXOFVDLJLONNDW-UHFFFAOYSA-N
CAS Number
CAS 57-41-0
Pharmaceutical Properties Molecular Weight 252.27 Topological Polar Surface Area 58.2
Heavy Atom Count 19 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
XLogP
2.5
PubChem CID
1775
PubChem SID
10527886 ,10589150 ,11111069 ,11335682 ,11353793 ,11360921 ,11363999 ,11366561 ,11369123 ,11371880 ,11374526 ,11377285 ,11461893 ,11485017 ,11489097 ,11490706 ,11492799 ,11494919 ,11532994 ,14847761 ,17389903 ,17404941 ,24278370 ,26068808 ,26753026 ,26753027 ,26753028 ,29220975 ,3136997 ,4284342 ,46508847 ,47588955 ,47736431 ,47736432 ,47795039 ,48168464 ,48184955 ,48243361 ,48413692 ,48416427 ,48422573 ,5171921 ,592179 ,596082 ,74340 ,7847578 ,7980312 ,8151275 ,841957 ,9647
ChEBI ID
CHEBI:8107
TTD Drug ID
D0E4DW
DT(s) Transporting This Drug MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [2]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [3]
P-GP Transporter Info P-glycoprotein 1 Substrate [4]
References
1 Phenytoin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Evaluation of transport of common antiepileptic drugs by human multidrug resistance-associated proteins (MRP1, 2 and 5) that are overexpressed in pharmacoresistant epilepsy. Neuropharmacology. 2010 Jun;58(7):1019-32.
3 Upregulation of brain expression of P-glycoprotein in MRP2-deficient TR(-) rats resembles seizure-induced up-regulation of this drug efflux transporter in normal rats. Epilepsia. 2007 Apr;48(4):631-45.
4 The transport of antiepileptic drugs by P-glycoprotein. Adv Drug Deliv Rev. 2012 Jul;64(10):930-42.

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