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Felbamate

CAS No.
25451-15-4
Chemical Name:
Felbamate
Synonyms
W-554;Talox;Taloxa;Felbamyl;felbatol;felbamato;ADD-03055;FELBAMATE;Sch-54388;Felbanmate
CBNumber:
CB6689427
Molecular Formula:
C11H14N2O4
Molecular Weight:
238.24
MDL Number:
MFCD00865296
MOL File:
25451-15-4.mol
Last updated:2023-07-21 14:17:16

Felbamate Properties

Melting point 148-1500C
Boiling point 511.9±50.0 °C(Predicted)
Density 1.275±0.06 g/cm3(Predicted)
Flash point 9℃
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility alcohol: soluble
pka 12.99±0.50(Predicted)
form Solid
color White
BCS Class 2
CAS DataBase Reference 25451-15-4(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII X72RBB02N8
ATC code N03AX10
NIST Chemistry Reference Felbamate(25451-15-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS02,GHS06,GHS08
Signal word  Danger
Hazard statements  H225-H301+H311+H331-H370
Precautionary statements  P210-P260-P280-P301+P310-P311
RIDADR  UN1230 - class 3 - PG 2 - Methanol
WGK Germany  2
RTECS  TZ1070000
HS Code  2924296000
Toxicity LD50 i.p. in mice: 4000 mg/kg (Ludwig et al.)

Felbamate price More Price(35)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich F-029 Felbamate solution 2.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? 25451-15-4 1mL $146 2024-03-01 Buy
Sigma-Aldrich 1269312 Felbamate United States Pharmacopeia (USP) Reference Standard 25451-15-4 250mg $1530 2024-03-01 Buy
Cayman Chemical 18000 Felbamate ≥98% 25451-15-4 5mg $44 2024-03-01 Buy
Cayman Chemical 18000 Felbamate ≥98% 25451-15-4 10mg $74 2024-03-01 Buy
Sigma-Aldrich F0778 Felbamate 25451-15-4 10mg $155 2024-03-01 Buy
Product number Packaging Price Buy
F-029 1mL $146 Buy
1269312 250mg $1530 Buy
18000 5mg $44 Buy
18000 10mg $74 Buy
F0778 10mg $155 Buy

Felbamate Chemical Properties,Uses,Production

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.

Chemical Properties

White Powder. Solubility in water 0.33 mg/mL, in ethanol 5.0 mg/mL, and in DMF 333.4 mg/mL.

Originator

Carter-Wallace (U.S.A.)

Uses

Antiepileptic, structurally similar to meprobamate.

Definition

ChEBI: The bis(carbamate ester) of 2-phenylpropane-1,3-diol. An anticonvulsant, it is used in the treatment of epilepsy.

brand name

Felbatol

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.

Hazard

Low toxicity by ingestion. Human systemic effects.

Biological Activity

Anticonvulsant, acting as an antagonist at the NMDA-associated glycine binding site.

Biochem/physiol Actions

Anticonvulsant agent that is an allosteric antagonist at the NR2B subunit of the NMDA glutamate receptor; also has γ-aminobutyric acid (GABAA) receptor agonist properties.

Mechanism of action

Gabapentin is a water-soluble amino acid originally designed to be a GABA-mimetic analogue capable of penetrating the CNS. Surprisingly, it has no direct GABA-mimetic activity, nor is it active on sodium channels. The mechanism of action remains unknown, although it has been suggested that gabapentin may alter the metabolism or release of GABA. Gabapentin raises brain GABA levels in patients with epilepsy. Recent studies have demonstrated gabapentin binding to calcium channels in a manner that can be allosterically modulated.
Gabapentin is indicated as an adjunct for use against partial seizures with or without secondary generalization, in patients older than 12 years, and as adjunct for the treatment of partial seizures in children 3 to 12 years of age. It also is approved for the treatment of postherpetic neuralgia.

Pharmacokinetics

The pharmacokinetic properties for gabapentin generally are favorable, with a bioavailability of 60% when given in low doses and somewhat less when given at higher doses because of saturable intestinal uptake by the L-amino-acid transporter. The L-amino-acid transporter is very susceptible to substrate saturation (low Km value). Its absorption and distribution into the CNS appears to be dependent on this amino acid transporter. Following the administration of an oral dose, gabapentin reaches peak plasma concentration in 2 to 3 hours. Additionally, it exhibits linear pharmacokinetics. Moreover, it is not extensively metabolized, nor is it an inducer of hepatic metabolizing enzymes. The elimination of unmetabolized gabapentin occurs by the renal route. Although its therapeutic range is not well characterized, gabapentin has a broad therapeutic index. This implies that a wide range of doses can be used, based on individual patient needs, without significant limitation because of dose-dependent side effects. Protein binding is negligible. Its elimination half-life of 5 to 7 hours is not affected by the dose or by other drugs, and its short half-life necessitates multiple daily administration.

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

Side effects

Adverse effects of gabapentin are uncommon and not serious. The CNS effects include mild to moderate sedation, fatigue, ataxia, headache, dizziness, and diplopia. Gabapentin may exacerbate myoclonus, but the effect is mild and does not require discontinuance of the drug. It has been associated with the development of neuropsychiatric adverse events in children.
Drug interactions are infrequent with gabapentin. It does not induce hepatic metabolizing enzymes, nor do other AEDs affect its metabolism and elimination. Antacids may decrease absorption. Gabapentin dosage may need to be decreased in patients with renal disease or in the elderly.

Synthesis

The synthesis of felbamate was first published in 1959. 2-Phenyl-1,3-propanediole is reacted with ethylcarbamate to yield felbamate.

Veterinary Drugs and Treatments

Felbamate is an anticonvulsant agent that may useful for treating seizure disorders (especially complex partial seizures) in dogs. A potential advantage of felbamate therapy is that when used alone or in combination with phenobarbital and/or bromides, it does not appear to cause additive sedation.

Metabolism

Although the metabolism of felbamate has not been fully characterized, felbamate is esterase hydrolyzed to its monocarbamate metabolite, 2-phenyl-1,3-propanediol monocarbamate, which subsequently is oxidized via aldehyde dehydrogenase to its major human metabolite 3-carbamoyl-2-phenylpropionic acid. Other metabolites include the p-hydroxy and mercapturic acid metabolites of felbamate, which have been identified in human urine. Felbamate is a substrate for CYP2C19, with minor activity for CYP3A4 and CYP2E1. Thompson et al. has provided evidence for the formation of the reactive metabolite, 3-carbamoyl-2-phenylpropionaldehyde (CBMA), from the alcohol oxidation of 2-phenyl-1,3-propanediol monocarbamate. CBMA then undergoes spontaneous elimination to another reactive intermediate, 2-phenylpropenal (more commonly known as atropaldehyde), which is proposed to play a role in the development of toxicity during felbamate therapy. CBMA or a further product has been shown to provoke an immune response in mice. Evidence for in vivo atropaldehyde formation was confirmed with the identification of its mercapturic acid conjugates in human urine after felbamate administration. This is consistent with the hypothesis that atropaldehyde reacts rapidly with thiol nucleophiles, such as glutathione, to form mercapturates. More recently, a fluorine analogue of felbamate was synthesized in which the benzylic C2 hydrogen of the propane chain was replaced with fluorine, preventing the formation of atropaldehyde and confirming that the acidic benzylic hydrogen plays a pivotal role in its formation. This analogue is presently undergoing drug development. Felbamate administration exhibited linear kinetics, with a half-life of 20 to 23 hours in the absence of enzyme-inducing AEDs. Approximately 50% of an oral dose of felbamate is excreted unchanged.

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View Lastest Price from Felbamate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Felbamate USP/EP/BP pictures 2021-07-23 Felbamate USP/EP/BP
25451-15-4
US $1.10 / g 1g 99.9% 100 Tons min Dideu Industries Group Limited
felbamate pictures 2019-07-10 felbamate
25451-15-4
US $8.80 / KG 1KG 97%-99% 100kg Career Henan Chemical Co
  • felbamate pictures
  • felbamate
    25451-15-4
  • US $8.80 / KG
  • 97%-99%
  • Career Henan Chemical Co

Felbamate Spectrum

1,3-Propanediol, 2-phenyl-, dicarbamate (3-aminocarbonyloxy-2-phenyl-propyl) carbamate (3-carbamoyloxy-2-phenylpropyl) carbamate carbamic acid (3-carbamoyloxy-2-phenyl-propyl) ester Felbamate (250 mg) 3-propanediol,2-phenyl-dicarbamate ADD-03055 carbamicacid,2-phenyltrimethyleneester felbamato 1,3-Propanediol,2-phenyl-, 1,3-dicarbaMate 1,3-Propanediol, 2-phenyl-, dicarbamate (8CI,9CI) Felbamyl Taloxa W-554 FELBAMATE felbatol Felbanmate FELBAMATE (2-PHENYL-1,3-PROPANEDIOL DICA FELBAMATE 99.0% 2-PhenyltrimethyleneEster Talox 2-phenylpropane-1,3-diyl dicarbamate 2-PHENYL-1,3-PROPANEDIOL DICARBAMATE Dicarbamic acid 2-phenyltrimethylene ester Sch-54388 Felbamate solution Felbamate, 98.0+ % (HPLC) Felbamate USP/EP/BP Felbamate (W-554 FelbamateQ: What is Felbamate Q: What is the CAS Number of Felbamate Q: What is the storage condition of Felbamate Q: What are the applications of Felbamate Felbamate (1269312) R)-Daurisoline Felbamate (3-carbamoyloxy-2-phenylpropyl) carbamate 25451-15-4 23824 Heterocyclic Compounds Glutamate receptor Intermediates & Fine Chemicals Pharmaceuticals Inhibitors