Felbamate

Base Information

• Chemical Name: Felbamate
• CAS No.: 25451-15-4
• Molecular Formula: C11H14N2O4
• Molecular Weight: 238.243
• Hs Code.: 2924296000
• European Community (EC) Number: 247-001-4
• NSC Number: 759866
• UNII: X72RBB02N8
• DSSTox Substance ID: DTXSID9023041
• Nikkaji Number: J50.906J
• Wikipedia: Felbamate
• Wikidata: Q421301
• NCI Thesaurus Code: C47530
• RXCUI: 24812
• Pharos Ligand ID: T5XG6NK31BLB
• Metabolomics Workbench ID: 43208
• ChEMBL ID: CHEMBL1094
• Mol file: 25451-15-4.mol

Synonyms:(3-Carbamoyloxy-2-phenyl-propyl) carbamate;2 Phenyl 1,3 propanediol dicarbamate;2-phenyl-1,3-propanediol dicarbamate;ADD 03055;ADD-03055;ADD03055;felbamate;Felbamyl;Felbatol;Taloxa;W 554;W-554;W554

Chemical Property of Felbamate

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.36E-10mmHg at 25°C
• Melting Point: 148-150 °C
• Refractive Index: 1.558
• Boiling Point: 511.9 °C at 760 mmHg
• PKA: 12.99±0.50(Predicted)
• Flash Point: 288.4 °C
• PSA: 104.64000
• Density: 1.275 g/cm³
• LogP: 2.36140
• Storage Temp.: Store at RT
• Solubility.: alcohol: soluble
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 238.09535693
• Heavy Atom Count: 17
• Complexity: 246

Purity/Quality:

99%, ^*data from raw suppliers

Felbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Anticonvulsants
• Canonical SMILES: C1=CC=C(C=C1)C(COC(=O)N)COC(=O)N
• Recent ClinicalTrials: Population Pharmacokinetics of Antiepileptic in Pediatrics
• Description: Felbamate, characterized by its low toxicity and wide margin of safety, is efficacious in treating refractory patients with generalized tonic-clonic and complex partial seizures as monotherapy and adjunctive therapy.It has also been demonstrated to have a neuroprotective effect in cerebral ischemia and hypoxia. It has been suggested that the mechanism of its anticonvulsant activity is possibly through an interaction with the strychnineinsensitive receptor site on the NMDA receptor complex.
• Biological Functions: Felbamate (Felbatol) was introduced with the expectation that it would become a major drug in the treatment of epilepsy. Felbamate exhibited few manifestations of serious toxicity in early clinical trials. Soon after its introduction, however, it became apparent that its use was associated with a high incidence of aplastic anemia. Consequently, felbamate is indicated only for patients whose epilepsy is so severe that the risk of aplastic anemia is considered acceptable. While its mechanism of action has not been clearly established, felbamate shows some activity as an inhibitor of voltage-dependent sodium channels in a manner similar to that of phenytoin and carbamazepine. Felbamate also interacts at the strychnine-insensitive glycine recognition site on the NMDA receptor– ionophore complex.Whether this effect is important to its anticonvulsant activity is not clear.
• Clinical Use: Felbamate is a dicarbamate that is structurally similar to the antianxiety drug meprobamate. It was approved by the U.S. FDA for antiseizure use in 1993. Following the occurrence of rare cases of aplastic anemia and of severe hepatotoxicity associated with the use of felbamate during early 1994, however, a black box warning was added to the drug's package insert). Despite this, felbamate continues to be used in many patients, although not as a first-line treatment. These toxicity effects may be attributed to the formation of toxic metabolites. Although felbamate use is now uncommon, it is used for severe refractory seizures, either partial, myoclonic, or atonic, or in Lennox-Gastaut syndrome

Technology Process of Felbamate

There total 11 articles about Felbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

→ felbamate (25451-15-4)

Guidance literature:

In methanol; water; at 2 - 70 ℃; for 2.25h; Purification / work up;

Reference yield: 82.0%

2-fluoro-2-phenyl-1,3-propanediol (211506-14-8) → felbamate (25451-15-4)

Guidance literature:

Reference yield: 78.0%

2-phenylpropane-1, 3-diol (1570-95-2) + 1,1'-carbonyldiimidazole (530-62-1) + 2-fluoro-2-phenyl-1,3-propanediol (211506-14-8) → Fluorofelbamate (726-99-8) + Fluoro monocarbamate felbamate (288302-42-1) + 2-phenyl-1,3-propanediol monocarbamate (25451-53-0) + felbamate (25451-15-4)

Guidance literature:

2-phenylpropane-1, 3-diol; 1,1'-carbonyldiimidazole; 2-fluoro-2-phenyl-1,3-propanediol; In tetrahydrofuran;

With ammonium carbonate; In tetrahydrofuran; for 38 - 72h; Molecular sieve;

upstream raw materials:

2-phenylpropane-1, 3-diol

urethane

2-phenyl-1,3-propanediol monocarbamate

1,1'-carbonyldiimidazole

Refernces

• 1、 Pe?a-López, Miguel,Neumann, Helfried,Beller, Matthias. "Iron-catalyzed reaction of urea with alcohols and amines: A safe alternative for the synthesis of primary carbamates". . p. 2233 - 2238. Retrieved 2017/07/25.
• 2、 -. "FELBAMATE WITH IMPROVED BULK DENSITY". Page/Page column 3-4. . Retrieved 2009/05/28.