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Identification
NameFelbamate
Accession NumberDB00949  (APRD00505)
TypeSmall Molecule
GroupsApproved
Description

Felbamate is an anticonvulsant drug used in the treatment of epilepsy. It is used to treat partial seizures (with and without generalization) in adults and partial and generalized seizures associated with Lennox-Gastaut syndrome in children. It has a weak inhibitory effect on GABA receptor binding sites.

Structure
Thumb
Synonyms
SynonymLanguageCode
2-Phenyl-1,3-propanediol dicarbamateNot AvailableNot Available
Carbamic acid 2-phenyltrimethylene esterNot AvailableNot Available
Carbamic acid 3-carbamoyloxy-2-phenyl-propyl esterNot AvailableNot Available
FelbamateNot AvailableNot Available
FelbamatoNot AvailableNot Available
FelbamatumNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Felbatoltablet400 mgoralMeda Pharmaceuticals Inc.1993-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Felbatoltablet600 mgoralMeda Pharmaceuticals Inc.1993-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Felbatolsuspension600 mg/5mLoralMeda Pharmaceuticals Inc.1993-07-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Felbamatetablet400 mgoralWallace Pharmaceuticals Inc.2011-11-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Felbamatetablet600 mgoralWallace Pharmaceuticals Inc.2011-11-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Felbamatesuspension600 mg/5mLoralWallace Pharmaceuticals Inc.2011-11-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Felbamatesuspension600 mg/5mLoralAmneal Pharmaceuticals2011-12-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Felbamatetablet400 mgoralAmneal Pharmaceuticals2011-09-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Felbamatetablet600 mgoralAmneal Pharmaceuticals2011-09-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Felbamatetablet600 mgoralCarilion Materials Management2011-09-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
FelbamylNot Available
TaloxaNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number25451-15-4
WeightAverage: 238.2399
Monoisotopic: 238.095356946
Chemical FormulaC11H14N2O4
InChI KeyWKGXYQFOCVYPAC-UHFFFAOYSA-N
InChI
InChI=1S/C11H14N2O4/c12-10(14)16-6-9(7-17-11(13)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,12,14)(H2,13,15)
IUPAC Name
3-(carbamoyloxy)-2-phenylpropyl carbamate
SMILES
NC(=O)OCC(COC(N)=O)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor use only in those patients who respond inadequately to alternative treatments and whose epilepsy is so severe that a substantial risk of aplastic anemia and/or liver failure is deemed acceptable in light of the benefits conferred by its use.
PharmacodynamicsFelbamate is an antiepileptic indicated as monotherapy or as an adjunct to other anticonvulsants for the treatment of partial seizures resulting from epilepsy. Receptor-binding studies in vitro indicate that felbamate has weak inhibitory effects on GABA-receptor binding, benzodiazepine receptor binding, and is devoid of activity at the MK-801 receptor binding site of the NMDA receptor-ionophore complex. However, felbamate does interact as an antagonist at the strychnine-insensitive glycine recognition site of the NMDA receptor-ionophore complex.
Mechanism of actionThe mechanism by which felbamate exerts its anticonvulsant activity is unknown, but in animal test systems designed to detect anticonvulsant activity, felbamate has properties in common with other marketed anticonvulsants. In vitro receptor binding studies suggest that felbamate may be an antagonist at the strychnine-insensitive glycine-recognition site of the N-methyl-D-aspartate (NMDA) receptor-ionophore complex. Antagonism of the NMDA receptor glycine binding site may block the effects of the excitatory amino acids and suppress seizure activity. Animal studies indicate that felbamate may increase the seizure threshold and may decrease seizure spread. It is also indicated that felbamate has weak inhibitory effects on GABA-receptor binding, benzodiazepine receptor binding.
Absorption>90%
Volume of distribution
  • 756±82 mL/kg
Protein binding20-36%
Metabolism

Hepatic

SubstrateEnzymesProduct
Felbamate
2-Phenyl-1,3-propanediol monocarbamateDetails
Felbamate
p-HydroxyfelbamateDetails
Felbamate
2-HydroxyfelbamateDetails
2-Phenyl-1,3-propanediol monocarbamate
3-Carbamoyl-2-phenylpropionaldehydeDetails
3-Carbamoyl-2-phenylpropionaldehyde
Not Available
AtropaldehydeDetails
3-Carbamoyl-2-phenylpropionaldehyde
Not Available
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-oneDetails
3-Carbamoyl-2-phenylpropionaldehyde
3-Carbamoyl-2-phenylpropionic acidDetails
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one
5-Phenyl-1,3-oxazinane-2,4-dioneDetails
5-Phenyl-1,3-oxazinane-2,4-dione
Not Available
3-Carbamoyl-2-phenylpropionic acidDetails
Route of eliminationNot Available
Half life20-23 hours
Clearance
  • 26 +/- 3 mL/hr/kg [single 1200 mg dose]
  • 30 +/- 8 mL/hr/kg [multiple daily doses of 3600 mg]
ToxicityLD50=5000 mg/kg (Orally in rats)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9544
Blood Brain Barrier+0.9805
Caco-2 permeable-0.6324
P-glycoprotein substrateNon-substrate0.783
P-glycoprotein inhibitor INon-inhibitor0.9551
P-glycoprotein inhibitor IINon-inhibitor0.932
Renal organic cation transporterNon-inhibitor0.9039
CYP450 2C9 substrateNon-substrate0.9009
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7942
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9184
CYP450 2D6 substrateInhibitor0.7126
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9271
Ames testNon AMES toxic0.7602
CarcinogenicityNon-carcinogens0.8338
BiodegradationNot ready biodegradable0.8068
Rat acute toxicity1.7095 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9872
hERG inhibition (predictor II)Non-inhibitor0.9786
Pharmacoeconomics
Manufacturers
  • Meda pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Suspensionoral600 mg/5mL
Tabletoral400 mg
Tabletoral600 mg
Prices
Unit descriptionCostUnit
Felbatol 600 mg tablet3.1USD tablet
Felbatol 400 mg tablet2.71USD tablet
Felbatol 600 mg/5ml Suspension1.43USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States49786801992-09-262009-09-26
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point151.5 °CPhysProp
water solubilitySlightly soluble in waterNot Available
logP0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.742 mg/mLALOGPS
logP0.56ALOGPS
logP0.68ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.64 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity59.59 m3·mol-1ChemAxon
Polarizability23.52 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS
References
Synthesis ReferenceNot Available
General Reference
  1. Leppik IE, Dreifuss FE, Pledger GW, Graves NM, Santilli N, Drury I, Tsay JY, Jacobs MP, Bertram E, Cereghino JJ, et al.: Felbamate for partial seizures: results of a controlled clinical trial. Neurology. 1991 Nov;41(11):1785-9. Pubmed
External Links
ATC CodesN03AX10
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (47.1 KB)
Interactions
Drug Interactions
Drug
AmobarbitalBarbiturates may decrease the serum concentration of Felbamate. Felbamate may increase the serum concentration of Barbiturates.
AprepitantMay increase the serum concentration of CYP3A4 Substrates.
AripiprazoleCYP3A4 Inducers may decrease the serum concentration of ARIPiprazole.
BosentanMay decrease the serum concentration of CYP3A4 Substrates.
BuprenorphineCNS Depressants may enhance the CNS depressant effect of Buprenorphine.
ButabarbitalBarbiturates may decrease the serum concentration of Felbamate. Felbamate may increase the serum concentration of Barbiturates.
ButalbitalBarbiturates may decrease the serum concentration of Felbamate. Felbamate may increase the serum concentration of Barbiturates.
ButethalMay decrease the serum concentration of Felbamate. Felbamate may increase the serum concentration of Barbiturates.
CarbamazepineCarBAMazepine may decrease the serum concentration of Felbamate. Felbamate may decrease the serum concentration of CarBAMazepine.
ConivaptanMay increase the serum concentration of CYP3A4 Substrates.
DabrafenibMay decrease the serum concentration of CYP3A4 Substrates.
DasatinibMay increase the serum concentration of CYP3A4 Substrates.
DeferasiroxMay decrease the serum concentration of CYP3A4 Substrates.
DesogestrelMay decrease the serum concentration of Contraceptives (Estrogens). Contraceptive failure is possible.
DoxylamineMay enhance the CNS depressant effect of CNS Depressants.
DronabinolMay enhance the CNS depressant effect of CNS Depressants.
DroperidolMay enhance the CNS depressant effect of CNS Depressants.
DrospirenoneMay decrease the serum concentration of Contraceptives (Progestins).
Ethinyl EstradiolMay decrease the serum concentration of Contraceptives (Estrogens). Contraceptive failure is possible.
EthynodiolMay decrease the serum concentration of Contraceptives (Estrogens). Contraceptive failure is possible.
EtonogestrelMay decrease the serum concentration of Contraceptives (Progestins).
FosaprepitantMay increase the serum concentration of CYP3A4 Substrates.
FosphenytoinFelbamate may increase the serum concentration of Fosphenytoin. Fosphenytoin may decrease the serum concentration of Felbamate.
HeptabarbitalMay decrease the serum concentration of Felbamate. Felbamate may increase the serum concentration of Barbiturates.
HexobarbitalMay decrease the serum concentration of Felbamate. Felbamate may increase the serum concentration of Barbiturates.
HydrocodoneCNS Depressants may enhance the CNS depressant effect of Hydrocodone.
HydroxyzineMay enhance the CNS depressant effect of CNS Depressants.
IvacaftorMay increase the serum concentration of CYP3A4 Substrates.
LevonorgestrelMay decrease the serum concentration of Contraceptives (Progestins).
LULICONAZOLEMay increase the serum concentration of CYP3A4 Substrates.
Magnesium SulfateMay enhance the CNS depressant effect of CNS Depressants.
Medroxyprogesterone AcetateMay decrease the serum concentration of Contraceptives (Progestins).
MefloquineMefloquine may diminish the therapeutic effect of Anticonvulsants. Mefloquine may decrease the serum concentration of Anticonvulsants.
MestranolMay decrease the serum concentration of Contraceptives (Estrogens). Contraceptive failure is possible.
MethohexitalBarbiturates may decrease the serum concentration of Felbamate. Felbamate may increase the serum concentration of Barbiturates.
MethotrimeprazineCNS Depressants may enhance the CNS depressant effect of Methotrimeprazine. Methotrimeprazine may enhance the CNS depressant effect of CNS Depressants.
MetyrosineCNS Depressants may enhance the sedative effect of Metyrosine.
MianserinMay diminish the therapeutic effect of Anticonvulsants.
MifepristoneMay increase the serum concentration of CYP3A4 Substrates.
MirtazapineCNS Depressants may enhance the CNS depressant effect of Mirtazapine.
MitotaneMay decrease the serum concentration of CYP3A4 Substrates.
NabiloneMay enhance the CNS depressant effect of CNS Depressants.
NorelgestrominMay decrease the serum concentration of Contraceptives (Estrogens). Contraceptive failure is possible.
NorethindroneMay decrease the serum concentration of Contraceptives (Progestins).
NorgestimateMay decrease the serum concentration of Contraceptives (Progestins).
OrlistatMay decrease the serum concentration of Anticonvulsants.
OrphenadrineCNS Depressants may enhance the CNS depressant effect of Orphenadrine.
PentobarbitalBarbiturates may decrease the serum concentration of Felbamate. Felbamate may increase the serum concentration of Barbiturates.
PerampanelMay enhance the CNS depressant effect of CNS Depressants.
PhenobarbitalFelbamate may increase the serum concentration of PHENobarbital. PHENobarbital may decrease the serum concentration of Felbamate.
PhenytoinMay increase the serum concentration of Phenytoin. Phenytoin may decrease the serum concentration of Felbamate.
PramipexoleCNS Depressants may enhance the sedative effect of Pramipexole.
PrimidoneMay increase serum concentrations of the active metabolite(s) of Primidone. Specifically, phenobarbital concentrations may increase. Primidone may decrease the serum concentration of Felbamate.
RopiniroleCNS Depressants may enhance the sedative effect of ROPINIRole.
RotigotineCNS Depressants may enhance the sedative effect of Rotigotine.
RufinamideMay enhance the adverse/toxic effect of CNS Depressants. Specifically, sleepiness and dizziness may be enhanced.
SaxagliptinCYP3A4 Inducers may decrease the serum concentration of Saxagliptin.
SecobarbitalBarbiturates may decrease the serum concentration of Felbamate. Felbamate may increase the serum concentration of Barbiturates.
SiltuximabMay decrease the serum concentration of CYP3A4 Substrates.
SimeprevirMay increase the serum concentration of CYP3A4 Substrates.
SuvorexantCNS Depressants may enhance the CNS depressant effect of Suvorexant.
TapentadolMay enhance the CNS depressant effect of CNS Depressants.
ThalidomideCNS Depressants may enhance the CNS depressant effect of Thalidomide.
TocilizumabMay decrease the serum concentration of CYP3A4 Substrates.
UlipristalFelbamate may decrease the serum concentration of Ulipristal.
Valproic AcidMay increase the serum concentration of Valproic Acid and Derivatives.
ZolpidemCNS Depressants may enhance the CNS depressant effect of Zolpidem.
Food Interactions
  • Taking it after a meal may reduce the incidence of adverse effects.

Targets

1. Glutamate receptor ionotropic, NMDA 2B

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 2B Q13224 Details

References:

  1. Kleckner NW, Glazewski JC, Chen CC, Moscrip TD: Subtype-selective antagonism of N-methyl-D-aspartate receptors by felbamate: insights into the mechanism of action. J Pharmacol Exp Ther. 1999 May;289(2):886-94. Pubmed
  2. Harty TP, Rogawski MA: Felbamate block of recombinant N-methyl-D-aspartate receptors: selectivity for the NR2B subunit. Epilepsy Res. 2000 Mar;39(1):47-55. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  4. Chang HR, Kuo CC: Molecular determinants of the anticonvulsant felbamate binding site in the N-methyl-D-aspartate receptor. J Med Chem. 2008 Mar 27;51(6):1534-45. Epub 2008 Feb 27. Pubmed
  5. Luszczki JJ, Danysz W, Czuczwar SJ: Interactions of MRZ 2/576 with felbamate, lamotrigine, oxcarbazepine and topiramate in the mouse maximal electroshock-induced seizure model. Pharmacology. 2008;81(3):259-65. Epub 2008 Feb 4. Pubmed

2. Glutamate receptor ionotropic, NMDA 3A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 3A Q8TCU5 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

3. Glutamate receptor ionotropic, NMDA 2A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 2A Q12879 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Enzymes

1. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Williams DA, Foye WO, Lemke TL. Foye’s principles of medicinal chemistry. Lippincott Williams & Wilkins; 2002.
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inducer

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12