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

Stem definitionDrug idCAS RN
3534 106308-44-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • rufinamide
  • inovelon
  • banzel
  • CGP-33101
  • CGP 33101
The precise mechanism(s) by which rufinamide exerts its antiepileptic effect is unknown. The results of in vitro studies suggest that the principal mechanism of action of rufinamide is modulation of the activity of sodium channels and, in particular, prolongation of the inactive state of the channel.
  • Molecular weight: 238.20
  • Formula: C10H8F2N4O
  • CLOGP: 0.51
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 1
  • TPSA: 73.80
  • ALOGS: -2.57
  • ROTB: 3
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1.40 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.03 mg/mL Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine) 1 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 191.92 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 85 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
fu (Fraction unbound in plasma) 0.75 % Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 0.753 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.411 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 89.743 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 2.286 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 68.480 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 82.980 % High 1
herg hERG pIC50 4.021 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 1.282 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 2.965 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 68.080 % High 1
kinase-safety-class ACVR2B,AXL,CAMK2D,CDK5,CDK9,EIF2AK3,ERBB2,GRK2,ITK,MAPK7,PDK1,PDK2,PDK4,PRKDC 14
kinase-selectivity-class AXL,GRK2 2
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 2.427 High 1
mh-clint Mouse hepatocyte intrinsic clearance 1.143 High 1
mppb Mouse plasma protein binding (% unbound) 72.770 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 2.254 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 81.120 % High 1
rh-clint Rat hepatocyte intrinsic clearance 1.766 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 96.730 % High 1
rppb Rat plasma protein binding (% unbound) 73.770 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 862.979 uM High 1

Approvals:

DateAgencyCompanyOrphan
Jan. 16, 2007 EMA Eisai Ltd
Nov. 14, 2008 FDA EISAI INC

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
Seizure 364.08 55.34 119 1181 152510 90474637
Drug resistance 242.16 55.34 61 1239 30388 90596759
Multiple-drug resistance 155.30 55.34 33 1267 7743 90619404
Drug ineffective 127.35 55.34 124 1176 1384174 89242973
Status epilepticus 97.81 55.34 27 1273 18847 90608300
Stillbirth 79.70 55.34 19 1281 7424 90619723
Atonic seizures 57.55 55.34 10 1290 806 90626341

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
Seizure 254.88 49.44 113 1545 120448 42499229
Multiple-drug resistance 178.63 49.44 44 1614 7278 42612399
Status epilepticus 167.56 49.44 49 1609 15529 42604148
Tonic convulsion 130.23 49.44 26 1632 1633 42618044
Drug ineffective 96.30 49.44 119 1539 630078 41989599
Epilepsy 93.75 49.44 36 1622 26135 42593542
Petit mal epilepsy 89.23 49.44 22 1636 3628 42616049
Somnolence 82.70 49.44 57 1601 141048 42478629
Treatment failure 69.21 49.44 38 1620 62586 42557091
Aggression 63.58 49.44 32 1626 44131 42575546

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
Seizure 353.62 43.19 149 2569 221036 110365545
Status epilepticus 260.47 43.19 73 2645 31498 110555083
Multiple-drug resistance 243.59 43.19 58 2660 13177 110573404
Drug resistance 214.75 43.19 72 2646 56302 110530279
Tonic convulsion 161.82 43.19 32 2686 3042 110583539
Epilepsy 141.12 43.19 62 2656 100147 110486434
Drug ineffective 132.97 43.19 173 2545 1520367 109066214
Somnolence 131.97 43.19 85 2633 297364 110289217
Petit mal epilepsy 112.80 43.19 28 2690 7519 110579062
Generalised tonic-clonic seizure 80.65 43.19 35 2683 54645 110531936
Off label use 77.57 43.19 134 2584 1500051 109086530
Aggression 71.64 43.19 33 2685 59177 110527404
Drug interaction 68.23 43.19 72 2646 500111 110086470
Myoclonic epilepsy 66.47 43.19 15 2703 2676 110583905
Atonic seizures 60.63 43.19 12 2706 1142 110585439
Seizure cluster 58.20 43.19 11 2707 822 110585759
Stillbirth 49.80 43.19 13 2705 4251 110582330
Anticonvulsant drug level increased 49.79 43.19 12 2706 2846 110583735
Fanconi syndrome 47.31 43.19 12 2706 3507 110583074
Behaviour disorder 43.37 43.19 14 2704 9633 110576948

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N03AF03 NERVOUS SYSTEM
ANTIEPILEPTICS
ANTIEPILEPTICS
Carboxamide derivatives
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
MeSH PA D061567 Voltage-Gated Sodium Channel Blockers
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35623 anticonvulsant

Related Drugs by ATC class:

N03AF Carboxamide derivatives 3 drugs
carbamazepineeslicarbazepine acetateoxcarbazepine

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

DiseaseRelationSNOMED_IDDOID
Lennox-Gastaut syndrome indication 230418006
Atypical absence seizure off-label use 23374007
Atonic seizure off-label use 42365007
Absence seizure off-label use 79631006
Suicidal thoughts contraindication 6471006
Depressive disorder contraindication 35489007
Hepatic failure contraindication 59927004
Shortened QT interval contraindication 77867006
Leukopenia contraindication 84828003 DOID:615
Disease of liver contraindication 235856003 DOID:409
Renal dialysis contraindication 265764009
Breastfeeding (mother) contraindication 413712001




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.56 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 alpha subunit Ion channel BLOCKER CHEMBL CHEMBL
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 6.46 CHEMBL

External reference:

IDSource
4025270 VUID
N0000179367 NUI
D05775 KEGG_DRUG
4025270 VANDF
C0213404 UMLSCUI
CHEBI:134966 CHEBI
CHEMBL1201754 ChEMBL_ID
DB06201 DRUGBANK_ID
129228 PUBCHEM_CID
C079703 MESH_SUPPLEMENTAL_RECORD_UI
7470 IUPHAR_LIGAND_ID
7387 INN_ID
WFW942PR79 UNII
69036 RXNORM
158992 MMSL
24915 MMSL
340515 MMSL
d07069 MMSL
012301 NDDF
429802008 SNOMEDCT_US
429835003 SNOMEDCT_US
WFW942PR79 INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Rufinamide HUMAN PRESCRIPTION DRUG LABEL 1 0054-0425 TABLET, FILM COATED 200 mg ORAL ANDA 26 sections
Rufinamide HUMAN PRESCRIPTION DRUG LABEL 1 0054-0426 TABLET, FILM COATED 400 mg ORAL ANDA 26 sections
Rufinamide HUMAN PRESCRIPTION DRUG LABEL 1 0054-0528 SUSPENSION 40 mg ORAL ANDA 27 sections
Rufinamide HUMAN PRESCRIPTION DRUG LABEL 1 31722-598 TABLET, FILM COATED 200 mg ORAL ANDA 25 sections
Rufinamide HUMAN PRESCRIPTION DRUG LABEL 1 31722-599 TABLET, FILM COATED 400 mg ORAL ANDA 25 sections
Rufinamide HUMAN PRESCRIPTION DRUG LABEL 1 31722-688 SUSPENSION 40 mg ORAL ANDA 25 sections
RUFINAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 42571-391 TABLET 200 mg ORAL ANDA 26 sections
RUFINAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 42571-392 TABLET 400 mg ORAL ANDA 26 sections
RUFINAMIDE Human Prescription Drug Label 1 59651-563 SUSPENSION 40 mg ORAL ANDA 27 sections
Rufinamide Human Prescription Drug Label 1 59651-616 TABLET, FILM COATED 200 mg ORAL ANDA 26 sections
Rufinamide Human Prescription Drug Label 1 59651-617 TABLET, FILM COATED 400 mg ORAL ANDA 26 sections
Rufinamide HUMAN PRESCRIPTION DRUG LABEL 1 60687-824 SUSPENSION 40 mg ORAL ANDA 26 sections
Banzel HUMAN PRESCRIPTION DRUG LABEL 1 62856-582 TABLET, FILM COATED 200 mg ORAL NDA 32 sections
Banzel HUMAN PRESCRIPTION DRUG LABEL 1 62856-583 TABLET, FILM COATED 400 mg ORAL NDA 32 sections
Banzel HUMAN PRESCRIPTION DRUG LABEL 1 62856-584 SUSPENSION 40 mg ORAL NDA 32 sections
Rufinamide Human Prescription Drug Label 1 67877-673 SUSPENSION 40 mg ORAL ANDA 23 sections
Rufinamide HUMAN PRESCRIPTION DRUG LABEL 1 68180-797 SUSPENSION 40 mg ORAL ANDA 26 sections
RUFINAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 68180-802 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections
RUFINAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 68180-803 TABLET, FILM COATED 200 mg ORAL ANDA 26 sections
RUFINAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 68180-804 TABLET, FILM COATED 400 mg ORAL ANDA 26 sections
rufinamide HUMAN PRESCRIPTION DRUG LABEL 1 68462-713 TABLET, FILM COATED 200 mg ORAL ANDA 24 sections
rufinamide HUMAN PRESCRIPTION DRUG LABEL 1 68462-714 TABLET, FILM COATED 400 mg ORAL ANDA 24 sections
Rufinamide HUMAN PRESCRIPTION DRUG LABEL 1 69452-223 SUSPENSION 40 mg ORAL ANDA 28 sections
Rufinamide Human Prescription Drug Label 1 72205-038 SUSPENSION 40 mg ORAL ANDA 23 sections
Rufinamide HUMAN PRESCRIPTION DRUG LABEL 1 72603-261 SUSPENSION 40 mg ORAL ANDA 25 sections