Felbamate

Title: Felbamate
CAS Registry Number: 25451-15-4
CAS Name: 2-Phenyl-1,3-propanediol dicarbamate
Additional Names: carbamic acid 2-phenyltrimethylene ester
Manufacturers' Codes: ADD-03055; W-554
Trademarks: Felbamyl (Wallace); Felbatol (Carter-Wallace); Taloxa (Schering-Plough)
Molecular Formula: C11H14N2O4
Molecular Weight: 238.24
Percent Composition: C 55.46%, H 5.92%, N 11.76%, O 26.86%
Literature References: Antiepileptic, structurally similar to meprobamate, q.v. Prepn: F. M. Berger, B. J. Ludwig, US 2884444 (1959 to Carter); B. J. Ludwig et al., J. Med. Chem. 12, 462 (1969). Use in treatment of epileptic seizures: R. D. Sofia, US 4978680 (1990 to Carter-Walace). HPLC determn in plasma: R. P. Remmel et al., Ther. Drug Monit. 12, 90 (1990). Pharmacology: E. A. Swinyard et al., Epilepsia 27, 27 (1986). Metabolism in animals: J. T. Yang et al., Drug Metab. Dispos. 19, 1126 (1991). Penetration of blood brain barrier: E. M. Cornford et al., Epilepsia 33, 944 (1992). Clinical pharmacokinetics: A. J. Wilensky et al., ibid. 26, 602 (1985). Clinical trial in refractory partial seizures: E. Faught et al., Neurology 43, 688 (1993). Efficacy in childhood epileptic encephalopathy (Lennox-Gastaut syndrome): F. J. Ritter et al., N. Engl. J. Med. 328, 29 (1993). Review of pharmacology, toxicology and clinical evaluation: R. D. Sofia et al., Epilepsy Res. Suppl. 3, 103-108 (1991).
Properties: White, odorless powder, mp 151-152°. Sparingly sol in water, methanol, ethanol, acetone and chloroform; freely sol in DMSO, 1-methyl-2-pyrrolidinone and DMF. LD50 i.p. in mice: 4000 mg/kg (Ludwig et al.).
Melting point: mp 151-152°
Toxicity data: LD50 i.p. in mice: 4000 mg/kg (Ludwig et al.)
Therap-Cat: Anticonvulsant.
Keywords: Anticonvulsant.
Felbinac Felinine Felodipine Fenadiazole Fenalamide

Felbamate
Felbamate.svg
Systematic (IUPAC) name
(3-carbamoyloxy-2-phenylpropyl) carbamate
Clinical data
Trade names Felbatol
AHFS/Drugs.com monograph
MedlinePlus a606011
Pregnancy cat. C (USA)
Legal status Unscheduled
Routes Oral
Pharmacokinetic data
Bioavailability > 90%
Metabolism Hepatic
Half-life 20-23 hours
Excretion  ?
Identifiers
CAS number 25451-15-4 YesY
ATC code N03AX10
PubChem CID 3331
DrugBank DB00949
ChemSpider 3214 YesY
UNII X72RBB02N8 YesY
KEGG D00536 YesY
ChEBI CHEBI:4995 YesY
ChEMBL CHEMBL1094 YesY
Chemical data
Formula C11H14N2O4 
Mol. mass 238.24
 YesY (what is this?)  (verify)

Felbamate (marketed under the brand name Felbatol by MedPointe) is an anti-epileptic drug [1] used in the treatment of epilepsy. It is used to treat partial seizures [2][3] (with and without generalization) in adults and partial and generalized seizures associated with Lennox-Gastaut syndrome in children. However, an increased risk of potentially fatal aplastic anemia and/or liver failure limit the drugs usage to severe refractory epilepsy.