felbamate Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
tranquillizers, propanediol and pentanediol derivatives 1140 25451-15-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • felbamate
  • felbamyl
  • felbatol
A PEGylated phenylcarbamate derivative that acts as an antagonist of NMDA RECEPTORS. It is used as an anticonvulsant, primarily for the treatment of SEIZURES in severe refractory EPILEPSY.
  • Molecular weight: 238.24
  • Formula: C11H14N2O4
  • CLOGP: 0.50
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 104.64
  • ALOGS: -2.51
  • ROTB: 7

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
2.40 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.70 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 45 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 251.84 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
July 29, 1993 FDA MEDA PHARMS

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 181.73 55.45 68 696 129441 53218861
Laryngeal stenosis 78.47 55.45 13 751 793 53347509
Unmasking of previously unidentified disease 71.04 55.45 12 752 823 53347479
Electrocardiogram ST segment elevation 69.53 55.45 15 749 3774 53344528
Tachycardia 64 55.45 31 733 108181 53240121
Cardiotoxicity 59.75 55.45 15 749 7284 53341018
Drug reaction with eosinophilia and systemic symptoms 59.55 55.45 21 743 32779 53315523
Electrocardiogram repolarisation abnormality 59.01 55.45 11 753 1323 53346979
Electrocardiogram QRS complex prolonged 58.13 55.45 14 750 5728 53342574
Systolic dysfunction 57.82 55.45 11 753 1476 53346826

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 295.05 54.77 103 639 103751 32409033
Generalised tonic-clonic seizure 71.19 54.77 24 718 20615 32492169
Drug ineffective 62.14 54.77 58 684 383419 32129365
Benzodiazepine drug level decreased 55.31 54.77 7 735 35 32512749

Pharmacologic Action:

SourceCodeDescription
ATC N03AX10 NERVOUS SYSTEM
ANTIEPILEPTICS
ANTIEPILEPTICS
Other antiepileptics
FDA PE N0000008486 Decreased Central Nervous System Disorganized Electrical Activity
CHEBI has role CHEBI:35623 antiepileptic
CHEBI has role CHEBI:63726 neuroprotective agents
MeSH PA D000927 Anticonvulsants
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018691 Excitatory Amino Acid Antagonists
MeSH PA D018377 Neurotransmitter Agents
FDA EPC N0000175753 Anti-epileptic Agent

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Epilepsy indication 84757009 DOID:1826
Lennox-Gastaut syndrome indication 230418006
Simple partial seizure indication 117891000119100
Suicidal thoughts contraindication 6471006
Torsades de pointes contraindication 31722008
Depressive disorder contraindication 35489007
Hepatic failure contraindication 59927004
Kidney disease contraindication 90708001 DOID:557
Prolonged QT interval contraindication 111975006
Liver function tests abnormal contraindication 166603001
Disease of blood AND/OR blood-forming organ contraindication 191124002 DOID:74
Disease of liver contraindication 235856003 DOID:409
Aplastic anemia contraindication 306058006 DOID:12449
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001
Porphyria contraindication 418470004
Congenital long QT syndrome contraindication 442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.24 acidic
pKa2 13.84 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
Glutamate receptor ionotropic, NMDA 2A Ion channel ANTAGONIST DRUGBANK CHEMBL
Glutamate receptor ionotropic, NMDA 2B Ion channel ANTAGONIST IC50 4.28 WOMBAT-PK CHEMBL

External reference:

IDSource
4020832 VUID
N0000148344 NUI
D00536 KEGG_DRUG
4020832 VANDF
C0060135 UMLSCUI
CHEBI:4995 CHEBI
CHEMBL1094 ChEMBL_ID
DB00949 DRUGBANK_ID
D000078328 MESH_DESCRIPTOR_UI
3331 PUBCHEM_CID
5686 INN_ID
5473 IUPHAR_LIGAND_ID
X72RBB02N8 UNII
224900 RXNORM
185493 MMSL
3074 MMSL
4715 MMSL
d03170 MMSL
004277 NDDF
371387009 SNOMEDCT_US
96194006 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Felbatol HUMAN PRESCRIPTION DRUG LABEL 1 0037-0430 TABLET 400 mg ORAL NDA 31 sections
Felbatol HUMAN PRESCRIPTION DRUG LABEL 1 0037-0431 TABLET 600 mg ORAL NDA 31 sections
Felbatol HUMAN PRESCRIPTION DRUG LABEL 1 0037-0442 SUSPENSION 600 mg ORAL NDA 31 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 0121-0891 SUSPENSION 600 mg ORAL ANDA 33 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 10135-601 TABLET 400 mg ORAL ANDA 28 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 10135-602 TABLET 600 mg ORAL ANDA 28 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 16714-775 SUSPENSION 600 mg ORAL ANDA 33 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 47781-627 TABLET 400 mg ORAL ANDA 32 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 47781-630 TABLET 600 mg ORAL ANDA 32 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 51525-0430 TABLET 400 mg ORAL NDA authorized generic 31 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 51525-0431 TABLET 600 mg ORAL NDA authorized generic 31 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 51525-0442 SUSPENSION 600 mg ORAL NDA authorized generic 31 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 51672-4172 SUSPENSION 600 mg ORAL ANDA 33 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 51672-4185 TABLET 400 mg ORAL ANDA 34 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 51672-4186 TABLET 600 mg ORAL ANDA 34 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 62559-730 TABLET 400 mg ORAL ANDA 31 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 62559-731 TABLET 600 mg ORAL ANDA 31 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 63629-1937 TABLET 400 mg ORAL ANDA 31 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 63629-1944 TABLET 600 mg ORAL ANDA 31 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 65162-686 SUSPENSION 600 mg ORAL ANDA 16 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 65162-734 TABLET 400 mg ORAL ANDA 15 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 65162-735 TABLET 600 mg ORAL ANDA 15 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 66689-825 SUSPENSION 600 mg ORAL ANDA 22 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 68151-4474 TABLET 600 mg ORAL ANDA 15 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 70771-1077 TABLET 400 mg ORAL ANDA 1 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 70771-1078 TABLET 600 mg ORAL ANDA 1 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 72578-056 TABLET 400 mg ORAL ANDA 27 sections
Felbamate HUMAN PRESCRIPTION DRUG LABEL 1 72578-057 TABLET 600 mg ORAL ANDA 27 sections