General Information of Drug (ID: DMXWOCP)

Drug Name
Ethotoin
Synonyms
Accenon; Ethotoine; Ethotoinum; Etotoina; Peganone; Pegoanone; Abbott brand of ethotoin; Accenon (TN); Ethotoine [INN-French]; Ethotoinum [INN-Latin]; Etotoina [INN-Spanish]; Peganone (TN); Ethotoin [INN:BAN:JAN]; Ethotoin (JAN/USP/INN); (+-)-3-Ethyl-5-phenylhydantoin; 1-Ethyl-2,5-dioxo-4-phenylimidazolidine; 3-Ethyl-5-phenyl-2,4-imidazolidinedione; 3-Ethyl-5-phenylhydantoin; 3-Ethyl-5-phenylimidazolidin-2,4-dione; 3-ethyl-5-phenylimidazolidine-2,4-dione
Indication
Disease Entry ICD 11 Status REF
Complex partial seizure 8A68.0 Approved [1]
Epilepsy with generalized tonic-clonic seizures N.A. Approved [2]
Therapeutic Class
Anticonvulsants
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 204.22
Logarithm of the Partition Coefficient (xlogp) 1
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Half-life
The concentration or amount of drug in body reduced by one-half in 3 - 9 hours [3]
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C11H12N2O2
IUPAC Name
3-ethyl-5-phenylimidazolidine-2,4-dione
Canonical SMILES
CCN1C(=O)C(NC1=O)C2=CC=CC=C2
InChI
InChI=1S/C11H12N2O2/c1-2-13-10(14)9(12-11(13)15)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,12,15)
InChIKey
SZQIFWWUIBRPBZ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3292
ChEBI ID
CHEBI:4888
CAS Number
86-35-1
DrugBank ID
DB00754
TTD ID
D05EPM
ACDINA ID
D00255
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Voltage-gated sodium channel alpha Nav1.5 (SCN5A) TTZOVE0 SCN5A_HUMAN Blocker [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Ethotoin
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Diazepam DM08E9O Moderate Increased metabolism of Ethotoin caused by Diazepam mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [5]
Methsuximide DM6L5VO Moderate Increased metabolism of Ethotoin caused by Methsuximide mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [6]
Tiagabine DMKSQG0 Moderate Increased metabolism of Ethotoin caused by Tiagabine mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [7]
Clonazepam DMTO13J Moderate Increased metabolism of Ethotoin caused by Clonazepam mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [5]
Coadministration of a Drug Treating the Disease Different from Ethotoin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Bepridil DM0RKS4 Moderate Increased metabolism of Ethotoin caused by Bepridil mediated induction of CYP450 enzyme. Angina pectoris [BA40] [8]
Nifedipine DMSVOZT Moderate Increased metabolism of Ethotoin caused by Nifedipine mediated induction of CYP450 enzyme. Angina pectoris [BA40] [8]
Bedaquiline DM3906J Moderate Increased risk of hepatotoxicity by the combination of Ethotoin and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [9]
Halazepam DMPFWO6 Moderate Increased metabolism of Ethotoin caused by Halazepam mediated induction of CYP450 enzyme. Anxiety disorder [6B00-6B0Z] [10]
Oxazepam DMXNZM4 Moderate Increased metabolism of Ethotoin caused by Oxazepam mediated induction of CYP450 enzyme. Anxiety disorder [6B00-6B0Z] [5]
Aminophylline DML2NIB Moderate Increased metabolism of Ethotoin caused by Aminophylline mediated induction of CYP450 enzyme. Asthma [CA23] [11]
Clarithromycin DM4M1SG Moderate Increased metabolism of Ethotoin caused by Clarithromycin mediated induction of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [12]
Troleandomycin DMUZNIG Moderate Increased metabolism of Ethotoin caused by Troleandomycin mediated induction of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [13]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Ethotoin and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [14]
Levomilnacipran DMV26S8 Moderate Antagonize the effect of Ethotoin when combined with Levomilnacipran. Chronic pain [MG30] [15]
Anisindione DM2C48U Moderate Increased metabolism of Ethotoin caused by Anisindione mediated induction of CYP450 enzyme. Coagulation defect [3B10] [16]
Olopatadine DMKMWQG Moderate Additive CNS depression effects by the combination of Ethotoin and Olopatadine. Conjunctiva disorder [9A60] [17]
Mivacurium DM473VD Moderate Increased metabolism of Ethotoin caused by Mivacurium mediated induction of CYP450 enzyme. Corneal disease [9A76-9A78] [18]
Pancuronium DMB0VY8 Moderate Increased metabolism of Ethotoin caused by Pancuronium mediated induction of CYP450 enzyme. Corneal disease [9A76-9A78] [18]
Tubocurarine DMBZIVP Moderate Increased metabolism of Ethotoin caused by Tubocurarine mediated induction of CYP450 enzyme. Corneal disease [9A76-9A78] [13]
Oxtriphylline DMLHSE3 Moderate Increased metabolism of Ethotoin caused by Oxtriphylline mediated induction of CYP450 enzyme. Cough [MD12] [19]
Mycophenolic acid DMRBMAU Minor Increased plasma concentration of Ethotoin and Mycophenolic acid due to competitive binding of plasma proteins. Crohn disease [DD70] [20]
Ethanol DMDRQZU Moderate Additive CNS depression effects by the combination of Ethotoin and Ethanol. Cystitis [GC00] [13]
Vilazodone DM4LECQ Moderate Antagonize the effect of Ethotoin when combined with Vilazodone. Depression [6A70-6A7Z] [15]
Vortioxetine DM6F1PU Moderate Antagonize the effect of Ethotoin when combined with Vortioxetine. Depression [6A70-6A7Z] [15]
Milnacipran DMBFE74 Moderate Antagonize the effect of Ethotoin when combined with Milnacipran. Depression [6A70-6A7Z] [15]
Escitalopram DMFK9HG Moderate Antagonize the effect of Ethotoin when combined with Escitalopram. Depression [6A70-6A7Z] [15]
Desvenlafaxine DMHD4PE Moderate Antagonize the effect of Ethotoin when combined with Desvenlafaxine. Depression [6A70-6A7Z] [15]
Esketamine DMVU687 Moderate Additive CNS depression effects by the combination of Ethotoin and Esketamine. Depression [6A70-6A7Z] [13]
Cannabidiol DM0659E Moderate Increased risk of hepatotoxicity by the combination of Ethotoin and Cannabidiol. Epileptic encephalopathy [8A62] [21]
Itraconazole DMCR1MV Moderate Increased metabolism of Ethotoin caused by Itraconazole mediated induction of CYP450 enzyme. Fungal infection [1F29-1F2F] [13]
Miconazole DMPMYE8 Moderate Decreased metabolism of Ethotoin caused by Miconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [22]
Ketoconazole DMPZI3Q Moderate Increased metabolism of Ethotoin caused by Ketoconazole mediated induction of CYP450 enzyme. Fungal infection [1F29-1F2F] [13]
Isoniazid DM5JVS3 Moderate Decreased metabolism of Ethotoin caused by Isoniazid mediated inhibition of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [13]
Rifampin DMA8J1G Moderate Increased metabolism of Ethotoin caused by Rifampin mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [23]
Brentuximab vedotin DMWLC57 Moderate Increased risk of hepatotoxicity by the combination of Ethotoin and Brentuximab vedotin. Hodgkin lymphoma [2B30] [24]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Ethotoin and Mipomersen. Hyper-lipoproteinaemia [5C80] [25]
Teriflunomide DMQ2FKJ Major Increased risk of hepatotoxicity by the combination of Ethotoin and Teriflunomide. Hyper-lipoproteinaemia [5C80] [26]
BMS-201038 DMQTAGO Major Increased risk of hepatotoxicity by the combination of Ethotoin and BMS-201038. Hyper-lipoproteinaemia [5C80] [27]
Levamlodipine DM92S6N Moderate Increased metabolism of Ethotoin caused by Levamlodipine mediated induction of CYP450 enzyme. Hypertension [BA00-BA04] [8]
Felodipine DMOSW35 Moderate Increased metabolism of Ethotoin caused by Felodipine mediated induction of CYP450 enzyme. Hypertension [BA00-BA04] [28]
Triazolam DMETYK5 Moderate Increased metabolism of Ethotoin caused by Triazolam mediated induction of CYP450 enzyme. Insomnia [7A00-7A0Z] [5]
Quazepam DMY4D87 Moderate Increased metabolism of Ethotoin caused by Quazepam mediated induction of CYP450 enzyme. Insomnia [7A00-7A0Z] [5]
Estazolam DMZGXUM Moderate Increased metabolism of Ethotoin caused by Estazolam mediated induction of CYP450 enzyme. Insomnia [7A00-7A0Z] [5]
Remimazolam DMLVSYX Moderate Increased metabolism of Ethotoin caused by Remimazolam mediated induction of CYP450 enzyme. Labour/delivery anaesthesia complication [JB0C] [10]
Hydroxychloroquine DMSIVND Moderate Antagonize the effect of Ethotoin when combined with Hydroxychloroquine. Malaria [1F40-1F45] [13]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Ethotoin and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [29]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Ethotoin and Idelalisib. Mature B-cell leukaemia [2A82] [30]
Allopregnanolone DMNLHAC Moderate Additive CNS depression effects by the combination of Ethotoin and Allopregnanolone. Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z] [31]
Lasmiditan DMXLVDT Moderate Additive CNS depression effects by the combination of Ethotoin and Lasmiditan. Migraine [8A80] [32]
Thalidomide DM70BU5 Moderate Additive CNS depression effects by the combination of Ethotoin and Thalidomide. Multiple myeloma [2A83] [17]
Ocrelizumab DMEZ2KH Moderate Additive immunosuppressive effects by the combination of Ethotoin and Ocrelizumab. Multiple sclerosis [8A40] [33]
Apraclonidine DMO4PVE Moderate Additive CNS depression effects by the combination of Ethotoin and Apraclonidine. Optic nerve disorder [9C40] [34]
Buprenorphine DMPRI8G Major Additive CNS depression effects by the combination of Ethotoin and Buprenorphine. Pain [MG30-MG3Z] [35]
Dexamethasone DMMWZET Moderate Increased metabolism of Ethotoin caused by Dexamethasone mediated induction of CYP450 enzyme. Rheumatoid arthritis [FA20] [36]
Leflunomide DMR8ONJ Major Increased risk of hepatotoxicity by the combination of Ethotoin and Leflunomide. Rheumatoid arthritis [FA20] [26]
Methylprednisolone DM4BDON Moderate Increased metabolism of Ethotoin caused by Methylprednisolone mediated induction of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [36]
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Ethotoin and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [21]
Prednisolone DMQ8FR2 Moderate Increased metabolism of Ethotoin caused by Prednisolone mediated induction of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [36]
Disulfiram DMCL2OK Moderate Decreased metabolism of Ethotoin caused by Disulfiram mediated inhibition of CYP450 enzyme. Substance abuse [6C40] [37]
Pipecuronium DM5F84A Moderate Increased metabolism of Ethotoin caused by Pipecuronium mediated induction of CYP450 enzyme. Tonus and reflex abnormality [MB47] [13]
⏷ Show the Full List of 56 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Stearic acid E00079 5281 Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Carboxymethylcellulose sodium E00621 Not Available Adsorbent; Binding agent; Disintegrant; Emulsifying agent; Suspending agent; Viscosity-controlling agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Ethotoin 250 mg tablet 250 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7183).
2 Ethotoin FDA Label
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
5 Backman JT, Olkkola KT, Ojala M, Laaksovirta H, Neuvonen PJ "Concentrations and effects of oral midazolam are greatly reduced in patients treated with carbamazepine or phenytoin." Epilepsia 37 (1996): 253-7. [PMID: 8598183]
6 Browne TR, Feldman RG, Buchanan RA, et al. "Methsuximide for complex partial seizures: efficacy, toxicity, clinical pharmacology, and drug interactions." Neurology 33 (1983): 414-8. [PMID: 6403891]
7 Product Information. Gabitril (tiagabine). Abbott Pharmaceutical, Abbott Park, IL.
8 Ahmad S "Nifedipine-phenytoin interaction." J Am Coll Cardiol 3 (1984): 1582. [PMID: 6425385]
9 Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
10 Murphy A, Wilbur K "Phenytoin-diazepam interaction." Ann Pharmacother 37 (2003): 659-63. [PMID: 12708941]
11 Crowley JJ, Cusack BJ, Jue SG, et al "Cigarette smoking and theophylline metabolism: effects of phenytoin." Clin Pharmacol Ther 42 (1987): 334-40. [PMID: 3621789]
12 Bachmann K, Schwartz JI, Forney RB Jr, Jauregui L "Single dose phenytoin clearance during erythromycin treatment." Res Commun Chem Pathol Pharmacol 46 (1984): 207-17. [PMID: 6515115]
13 Cerner Multum, Inc. "Australian Product Information.".
14 Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
15 Belcastro V, Costa C, Striano P "Levetiracetam-associated hyponatremia." Seizure 17 (2008): 389-90. [PMID: 18584781]
16 Koch-Weser J, Sellers EM "Drug interactions with coumarin anticoagulants (first of two parts)." N Engl J Med 285 (1971): 487-98. [PMID: 4397794]
17 Warrington SJ, Ankier SI, Turner P "Evaluation of possible interactions between ethanol and trazodone or amitriptyline." Neuropsychobiology 15 (1986): 31-7. [PMID: 3725002]
18 Liberman BA, Norman P, Hardy BG "Pancuronium-phenytoin interaction: a case of decreased duration of neuromuscular blockade." Int J Clin Pharmacol Ther Toxicol 26 (1988): 371-4. [PMID: 3220609]
19 Miller M, Cosgriff J, Kwong T, Morken DA "Influence of phenytoin on theophylline clearance." Clin Pharmacol Ther 35 (1984): 666-9. [PMID: 6713777]
20 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
21 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
22 Rolan PE, Somogyi AA, Drew MJ, et al "Phenytoin intoxication during treatment with parenteral miconazole." Br Med J (Clin Res Ed) 287 (1983): 1760. [PMID: 6416579]
23 Abajo FJ "Phenytoin interaction with rifampicin." Br Med J 297 (1988): 1048. [PMID: 3142625]
24 Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
25 Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
26 Canadian Pharmacists Association.
27 Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
28 Bahls FH, Ozuna J, Ritchie DE "Interactions between calcium channel blockers and the anticonvulsants carbamazepine and phenytoin." Neurology 41 (1991): 740-2. [PMID: 2027492]
29 Bodmer M, Sulz M, Stadlmann S, Droll A, Terracciano L, Krahenbuhl S "Fatal liver failure in an adult patient with acute lymphoblastic leukemia following treatment with L-asparaginase." Digestion 74 (2006): epub. [PMID: 16988508]
30 Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
31 Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
32 Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
33 Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
34 Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA.
35 Sekar M, Mimpriss TJ "Buprenorphine, benzodiazepines and prolonged respiratory depression." Anaesthesia 42 (1987): 567-8. [PMID: 3592200]
36 Frey BM, Frey FJ "Phenytoin modulates the pharmacokinetics of prednisolone and the pharmacodynamics of prednisolone as assessed by the inhibition of the mixed lymphocyte reaction in humans." Eur J Clin Invest 14 (1984): 1-6. [PMID: 6230241]
37 Brown CG, Kaminsky MJ, Feroli ER, Gurley HT "Delirium with phenytoin and disulfiram administration." Ann Emerg Med 12 (1983): 310-3. [PMID: 6625283]