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phenytoin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antiepileptics, hydantoin derivatives	2152	57-41-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: fenitoin sodium diphenylhydantoinate phenytoin diphantoin diphenylan diphenylhydantoin phenytoine phenytoinum phenytoin sodium	An anticonvulsant that is used to treat a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. The mechanism of therapeutic action is not clear, although several cellular actions have been described including effects on ion channels, active transport, and general membrane stabilization. The mechanism of its muscle relaxant effect appears to involve a reduction in the sensitivity of muscle spindles to stretch. Phenytoin has been proposed for several other therapeutic uses, but its use has been limited by its many adverse effects and interactions with other drugs. Molecular weight: 252.27 Formula: C15H12N2O2 CLOGP: 2.08 LIPINSKI: 0 HAC: 4 HDO: 2 TPSA: 58.20 ALOGS: -3.55 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

fenitoin
sodium diphenylhydantoinate
phenytoin
diphantoin
diphenylan
diphenylhydantoin
phenytoine
phenytoinum
phenytoin sodium

An anticonvulsant that is used to treat a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. The mechanism of therapeutic action is not clear, although several cellular actions have been described including effects on ion channels, active transport, and general membrane stabilization. The mechanism of its muscle relaxant effect appears to involve a reduction in the sensitivity of muscle spindles to stretch. Phenytoin has been proposed for several other therapeutic uses, but its use has been limited by its many adverse effects and interactions with other drugs.

Molecular weight: 252.27
Formula: C15H12N2O2
CLOGP: 2.08
LIPINSKI: 0
HAC: 4
HDO: 2
TPSA: 58.20
ALOGS: -3.55
ROTB: 2

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.30	g	O
0.30	g	P

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	90 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	2 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	19.82 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
t_half (Half-life)	16.80 hours	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.43 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.37 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.13 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.03 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
Jan. 6, 1953	FDA	PARKE DAVIS

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Seizure	2182.26	11.54	1249	40386	131385	63316002
Anticonvulsant drug level increased	736.28	11.54	176	41459	1341	63446046
Status epilepticus	667.52	11.54	281	41354	14952	63432435
Toxicity to various agents	549.64	11.54	740	40895	246510	63200877
Drug reaction with eosinophilia and systemic symptoms	535.94	11.54	312	41323	33524	63413863
Ataxia	527.82	11.54	238	41397	14957	63432430
Anticonvulsant drug level decreased	469.20	11.54	118	41517	1134	63446253
Generalised tonic-clonic seizure	463.31	11.54	269	41366	28747	63418640
Drug interaction	447.91	11.54	645	40990	228486	63218901
Nystagmus	384.26	11.54	147	41488	6073	63441314

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Seizure	1924.40	12.77	1284	37793	103573	34814281
Anticonvulsant drug level increased	734.29	12.77	198	38879	1418	34916436
Status epilepticus	719.51	12.77	328	38749	12286	34905568
Nystagmus	705.43	12.77	246	38831	4469	34913385
Toxicity to various agents	588.72	12.77	905	38172	199457	34718397
Ataxia	579.08	12.77	291	38786	13562	34904292
Drug reaction with eosinophilia and systemic symptoms	570.44	12.77	391	38686	32621	34885233
Anticonvulsant drug level decreased	530.13	12.77	141	38936	951	34916903
Anticonvulsant drug level above therapeutic	457.78	12.77	114	38963	568	34917286
Generalised tonic-clonic seizure	354.22	12.77	246	38831	20928	34896926

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Seizure	2516.75	11.13	1713	66264	187121	79489290
Status epilepticus	1166.73	11.13	521	67456	24520	79651891
Anticonvulsant drug level increased	1130.21	11.13	292	67685	2361	79674050
Drug reaction with eosinophilia and systemic symptoms	1080.51	11.13	676	67301	63568	79612843
Nystagmus	1049.46	11.13	373	67604	9531	79666880
Ataxia	1046.51	11.13	483	67494	24556	79651855
Toxicity to various agents	1000.91	11.13	1492	66485	420048	79256363
Anticonvulsant drug level decreased	676.03	11.13	182	67795	1752	79674659
Drug interaction	666.88	11.13	1234	66743	413949	79262462
Anticonvulsant drug level above therapeutic	653.50	11.13	160	67817	1011	79675400

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N03AB02	NERVOUS SYSTEM ANTIEPILEPTICS ANTIEPILEPTICS Hydantoin derivatives
ATC	N03AB52	NERVOUS SYSTEM ANTIEPILEPTICS ANTIEPILEPTICS Hydantoin derivatives
CHEBI has role	CHEBI:35623	anticonvulsants
CHEBI has role	CHEBI:38633	sodium channel blockers
CHEBI has role	CHEBI:50905	teratogeno
CHEBI has role	CHEBI:88188	allergenic drug
FDA EPC	N0000175753	Anti-epileptic Agent
FDA MoA	N0000185507	Cytochrome P450 2C9 Inducers
FDA MoA	N0000185607	Cytochrome P450 2C19 Inducers
FDA MoA	N0000187063	Cytochrome P450 2C8 Inducers

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Tonic-clonic seizure	indication	54200006
Epilepsy	indication	84757009	DOID:1826
Bipolar disorder in remission	indication	85248005
Localization-related epilepsy	indication	230381009	DOID:2234
Lennox-Gastaut syndrome	indication	230418006
Status epilepticus	indication	230456007	DOID:1824
Motor cortex epilepsy	indication	267592003
Tonic-clonic epilepsy	indication	352818000	DOID:7725
Epilepsy characterized by intractable complex partial seizures	indication	442481002
Simple partial seizure	indication	117891000119100

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🐶 Veterinary Drug Use

Species	Use	Relation
Dogs	Euthanasia	Indication

🐶 Veterinary products

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Product	Applicant	Ingredients
Beuthanasia-D Special	Intervet Inc.	2
Euthanasia-III Solution	Med-Pharmex Inc.	2
Euthasol	Virbac AH Inc.	2
Pentobarbital Sodium and Phenytoin Sodium	Akorn Animal Health Inc.	2

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Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	7.8	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Sodium channel protein type 9 subunit alpha	Ion channel	Q15858	SCN9A_HUMAN	BLOCKER			CHEMBL	CHEMBL
Sodium channel protein type 5 subunit alpha	Ion channel	Q14524	SCN5A_HUMAN	BLOCKER			WOMBAT-PK	CHEMBL
Sodium channel protein type 1 subunit alpha	Ion channel	P35498	SCN1A_HUMAN	BLOCKER			CHEMBL	CHEMBL
Sodium channel protein type 2 subunit alpha	Ion channel	Q99250	SCN2A_HUMAN	BLOCKER	IC50	4.90	IUPHAR	CHEMBL
Sodium channel protein type 3 subunit alpha	Ion channel	Q9NY46	SCN3A_HUMAN	BLOCKER			CHEMBL	CHEMBL
Sodium channel protein type 4 subunit alpha	Ion channel	P35499	SCN4A_HUMAN	BLOCKER	Ki	4.62	CHEMBL	CHEMBL
Sodium channel protein type 8 subunit alpha	Ion channel	Q9UQD0	SCN8A_HUMAN	BLOCKER			CHEMBL	CHEMBL
Nuclear receptor subfamily 1 group I member 3	Nuclear hormone receptor	Q14994	NR1I3_HUMAN				WOMBAT-PK
Sodium channel alpha subunits; brain (Types I, II, III)	Ion channel		SCN1A_RAT SCN2A_RAT SCN3A_RAT		IC50	4.40	CHEMBL
Sodium channel protein type 2 subunit alpha	Ion channel		SCN2A_RAT		IC50	4.66	CHEMBL

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External reference:

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ID	Source
001617	NDDF
001619	NDDF
1366	MMSL
1775	PUBCHEM_CID
2624	IUPHAR_LIGAND_ID
387220006	SNOMEDCT_US
387416005	SNOMEDCT_US
4017856	VUID
4017856	VANDF
4017857	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Dilantin	HUMAN PRESCRIPTION DRUG LABEL	1	0071-0369	CAPSULE	100 mg	ORAL	ANDA	28 sections
Dilantin	HUMAN PRESCRIPTION DRUG LABEL	1	0071-0369	CAPSULE	100 mg	ORAL	ANDA	28 sections
Dilantin	HUMAN PRESCRIPTION DRUG LABEL	1	0071-0369	CAPSULE	100 mg	ORAL	ANDA	28 sections
Dilantin	HUMAN PRESCRIPTION DRUG LABEL	1	0071-3740	CAPSULE	30 mg	ORAL	ANDA	28 sections
Dilantin	HUMAN PRESCRIPTION DRUG LABEL	1	0071-3740	CAPSULE	30 mg	ORAL	ANDA	28 sections
Dilantin	HUMAN PRESCRIPTION DRUG LABEL	1	0071-3740	CAPSULE	30 mg	ORAL	ANDA	28 sections
Dilantin Infatabs	HUMAN PRESCRIPTION DRUG LABEL	1	0071-0007	TABLET, CHEWABLE	50 mg	ORAL	ANDA	27 sections
Dilantin Infatabs	HUMAN PRESCRIPTION DRUG LABEL	1	0071-0007	TABLET, CHEWABLE	50 mg	ORAL	ANDA	27 sections
Dilantin-125	HUMAN PRESCRIPTION DRUG LABEL	1	0071-2214	SUSPENSION	125 mg	ORAL	NDA	28 sections
Dilantin-125	HUMAN PRESCRIPTION DRUG LABEL	1	0071-2214	SUSPENSION	125 mg	ORAL	NDA	28 sections

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