fosphenytoin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
antiepileptics, hydantoin derivatives 1247 93390-81-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • fosphenytoin
  • cerebyx
  • fosphenytoin sodium
  • fosphenytoin sodium hydrate
  • Molecular weight: 362.28
  • Formula: C16H15N2O6P
  • CLOGP: 0.81
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 3
  • TPSA: 116.17
  • ALOGS: -3.40
  • ROTB: 5
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.45 g P

ADMET properties:

PropertyValueReference
Vd (Volume of distribution) 0.06 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.05 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.16 hours Lombardo F, Berellini G, Obach RS
S (Water solubility) 142 mg/mL Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Bocci G, Oprea TI, Benet LZ
BA (Bioavailability) 0 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AKT3,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GRK3,GSK3B,IGF1R,ITK,JAK1,JAK2,JAK3,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAPK10,MAPK12,MAPK7,MAPK9,MAPKAPK2,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ZAP70 55
kinase-selectivity-class AURKA,AXL,BRAF,CDK4,CDK9,DDR1,EPHB4,ERBB2,GRK2,MAP2K6,MAPK7,PAK4,PDK4,PIK3CD,PRKDC,SIK2,STK33,SYK,TEK,ZAP70 20
pfas-class PFAS structural alert (1 = True, 0 = False) 0

Approvals:

DateAgencyCompanyOrphan
Aug. 5, 1996 FDA PARKE DAVIS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug ineffective 306.10 47.98 275 2345 1384023 89241804
Multiple-drug resistance 237.29 47.98 53 2567 7723 90618104
Status epilepticus 172.38 47.98 49 2571 18825 90607002
Myocardial depression 148.42 47.98 24 2596 609 90625218
Macroglossia 113.47 47.98 20 2600 859 90624968
Drug ineffective for unapproved indication 111.92 47.98 49 2571 66595 90559232
Cardiac arrest 107.92 47.98 55 2565 104880 90520947
Off label use 107.53 47.98 144 2476 1102108 89523719
Oropharyngeal oedema 79.45 47.98 13 2607 355 90625472
Atrioventricular block 71.98 47.98 21 2599 8794 90617033
Seizure 71.34 47.98 48 2572 152581 90473246
Acquired macroglossia 63.45 47.98 10 2610 214 90625613
Laryngeal stenosis 62.69 47.98 13 2607 1326 90624501
Hepatic function abnormal 52.59 47.98 26 2594 46262 90579565
Drug reaction with eosinophilia and systemic symptoms 48.52 47.98 24 2596 42734 90583093

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug ineffective 198.56 36.54 204 2141 629993 41988997
Status epilepticus 188.01 36.54 58 2287 15520 42603470
Multiple-drug resistance 113.02 36.54 33 2312 7289 42611701
Seizure 66.35 36.54 54 2291 120507 42498483
Drug ineffective for unapproved indication 56.96 36.54 34 2311 46129 42572861
Rhabdomyolysis 47.22 36.54 37 2308 77982 42541008
Haemodynamic instability 44.73 36.54 19 2326 12538 42606452
Nystagmus 44.18 36.54 15 2330 5381 42613609
Off label use 43.95 36.54 103 2242 638232 41980758
Cardiac arrest 40.15 36.54 39 2306 109281 42509709
Anticonvulsant drug level below therapeutic 39.93 36.54 9 2336 708 42618282
Hypotension 38.31 36.54 58 2287 257573 42361417

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug ineffective 457.84 35.34 429 4327 1520111 109064432
Status epilepticus 332.32 35.34 100 4656 31471 110553072
Multiple-drug resistance 225.10 35.34 61 4695 13174 110571369
Drug ineffective for unapproved indication 136.59 35.34 73 4683 102765 110481778
Myocardial depression 128.75 35.34 23 4733 709 110583834
Cardiac arrest 120.19 35.34 85 4671 196668 110387875
Off label use 110.75 35.34 215 4541 1499970 109084573
Seizure 109.07 35.34 84 4672 221101 110363442
Macroglossia 101.16 35.34 21 4735 1440 110583103
Nystagmus 77.41 35.34 26 4730 11551 110572992
Oropharyngeal oedema 71.24 35.34 13 4743 452 110584091
Anticonvulsant drug level below therapeutic 70.64 35.34 15 4741 1147 110583396
Drug reaction with eosinophilia and systemic symptoms 65.69 35.34 42 4714 82053 110502490
Propofol infusion syndrome 63.62 35.34 16 4740 2573 110581970
Hepatic function abnormal 62.46 35.34 42 4714 89253 110495290
Rhabdomyolysis 62.03 35.34 47 4709 120354 110464189
Hypotension 61.91 35.34 93 4663 523756 110060787
Bradycardia 59.50 35.34 51 4705 155466 110429077
Acquired macroglossia 57.68 35.34 10 4746 258 110584285
Laryngeal stenosis 56.97 35.34 13 4743 1385 110583158
Atrioventricular block 53.83 35.34 22 4734 16855 110567688
Anticonvulsant drug level above therapeutic 47.50 35.34 11 4745 1251 110583292
Respiratory depression 46.04 35.34 24 4732 31977 110552566
Anticonvulsant drug level increased 43.11 35.34 12 4744 2846 110581697
Blood pressure decreased 42.49 35.34 37 4719 115054 110469489
Drug interaction 40.48 35.34 75 4681 500108 110084435
Altered state of consciousness 40.03 35.34 27 4729 57599 110526944
Electrocardiogram QRS complex prolonged 38.22 35.34 16 4740 13005 110571538

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N03AB05 NERVOUS SYSTEM
ANTIEPILEPTICS
ANTIEPILEPTICS
Hydantoin derivatives
FDA PE N0000008486 Decreased Central Nervous System Disorganized Electrical Activity
MeSH PA D000927 Anticonvulsants
MeSH PA D002317 Cardiovascular Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D026941 Sodium Channel Blockers
MeSH PA D049990 Membrane Transport Modulators
CHEBI has role CHEBI:35623 anticonvulsant
FDA EPC N0000175753 Anti-epileptic Agent

Related Drugs by ATC class:

N03AB Hydantoin derivatives 4 drugs
amino(diphenylhydantoin) valeric acidethotoinmephenytoinphenytoin

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

DiseaseRelationSNOMED_IDDOID
Epilepsy indication 84757009 DOID:1826
Status epilepticus indication 230456007 DOID:1824
Epilepsy characterized by intractable complex partial seizures indication 442481002
Seizures in Neurosurgery indication
Alcoholism contraindication 7200002
Hyperphosphatemia contraindication 20165001 DOID:0050459
Complete atrioventricular block contraindication 27885002
Lymphadenopathy contraindication 30746006
Torsades de pointes contraindication 31722008
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Stokes-Adams syndrome contraindication 46935006
Sinus bradycardia contraindication 49710005
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:557
Prolonged QT interval contraindication 111975006
Hypoalbuminemia contraindication 119247004
Pancytopenia contraindication 127034005 DOID:12450
Second degree atrioventricular block contraindication 195042002
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Granulocytopenic disorder contraindication 417672002
Congenital long QT syndrome contraindication 442917000
HLA-B 1502 Positive Status contraindication




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 0.77 acidic
pKa2 5.83 acidic
pKa3 8.0 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Sodium channel protein type 5 subunit alpha Ion channel BLOCKER DRUGBANK CHEMBL

External reference:

IDSource
4024030 VUID
N0000022035 NUI
D02096 KEGG_DRUG
92134-98-0 SECONDARY_CAS_RN
4020973 VANDF
4024030 VANDF
C0244656 UMLSCUI
CHEBI:5165 CHEBI
CHEMBL1201336 ChEMBL_ID
DB01320 DRUGBANK_ID
CHEMBL919 ChEMBL_ID
C043114 MESH_SUPPLEMENTAL_RECORD_UI
56339 PUBCHEM_CID
7190 IUPHAR_LIGAND_ID
6484 INN_ID
B4SF212641 UNII
134860 RXNORM
117573 MMSL
4767 MMSL
6028 MMSL
d04041 MMSL
006181 NDDF
006182 NDDF
108397000 SNOMEDCT_US
372484000 SNOMEDCT_US
386843000 SNOMEDCT_US
B4SF212641 INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
CEREBYX HUMAN PRESCRIPTION DRUG LABEL 1 0069-5471 INJECTION, SOLUTION 50 mg INTRAVENOUS NDA 27 sections
CEREBYX HUMAN PRESCRIPTION DRUG LABEL 1 0069-5474 INJECTION, SOLUTION 50 mg INTRAVENOUS NDA 27 sections
CEREBYX HUMAN PRESCRIPTION DRUG LABEL 1 0069-6001 INJECTION, SOLUTION 50 mg INTRAVENOUS NDA 29 sections
Fosphenytoin Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0143-9782 INJECTION, SOLUTION 50 mg INTRAMUSCULAR ANDA 26 sections
Fosphenytoin Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0143-9788 INJECTION, SOLUTION 50 mg INTRAMUSCULAR ANDA 26 sections
Fosphenytoin Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0641-6136 INJECTION 50 mg INTRAMUSCULAR ANDA 26 sections
Fosphenytoin Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0641-6137 INJECTION 50 mg INTRAMUSCULAR ANDA 26 sections
Fosphenytoin Sodium HUMAN PRESCRIPTION DRUG LABEL 1 25021-798 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 31 sections
Fosphenytoin HUMAN PRESCRIPTION DRUG LABEL 1 63323-403 INJECTION, SOLUTION 50 mg INTRAMUSCULAR ANDA 31 sections
Fosphenytoin Sodium HUMAN PRESCRIPTION DRUG LABEL 1 65162-998 INJECTION 50 mg INTRAMUSCULAR ANDA 18 sections
Fosphenytoin Sodium HUMAN PRESCRIPTION DRUG LABEL 1 65162-999 INJECTION 50 mg INTRAMUSCULAR ANDA 18 sections
Fosphenytoin sodium Human Prescription Drug Label 1 68083-460 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 26 sections
Fosphenytoin sodium Human Prescription Drug Label 1 68083-461 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 26 sections
Fosphenytoin sodium HUMAN PRESCRIPTION DRUG LABEL 1 68462-621 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 25 sections
Fosphenytoin sodium HUMAN PRESCRIPTION DRUG LABEL 1 68462-622 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 25 sections
Fosphenytoin sodium HUMAN PRESCRIPTION DRUG LABEL 1 68462-945 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 25 sections