CAS 25451-15-4|felbamate

Introduction：Basic information about CAS 25451-15-4|felbamate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. felbamate BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles46
8. Synonyms

Common Name	felbamate
CAS Number	25451-15-4	Molecular Weight	238.240
Density	1.3±0.1 g/cm3	Boiling Point	511.9±50.0 °C at 760 mmHg
Molecular Formula	C₁₁H₁₄N₂O₄	Melting Point	148-1500C
MSDS	ChineseUSA	Flash Point	288.4±26.4 °C
Symbol	GHS02, GHS06, GHS08	Signal Word	Danger

Names

Name	felbamate
Synonym	More Synonyms

felbamate BiologicalActivity

Description	Felbamate (FBM) is a potent nonsedative anticonvulsant whose clinical effect may be related to the inhibition of N-methyl-D-aspartate (NMDA) .Target: NMDA ReceptorFelbamate (marketed under the brand name Felbatol by MedPointe) is an anti-epileptic 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. However, an increased risk of potentially fatal aplastic anemia and/or liver failure limit the drugs usage to severe refractory epilepsy.Felbamate has been proposed to a unique dual mechanism of action as a positive modulator of GABAA receptors and as a blocker of NMDA receptors, particularly isoforms containing the NR2B subunit. Although it is clear that felbamate does cause pharmacological inhibition of NMDA receptor of relevance of NMDA receptor blockade as a strategy for the treatment of human epilepsy has been questioned. Therefore, the importance of the effects of felbamate on NMDA receptors to its therapeutic action in epilepsy is uncertain.
Related Catalog	Signaling Pathways >>Membrane Transporter/Ion Channel >>iGluRSignaling Pathways >>Neuronal Signaling >>iGluRResearch Areas >>Neurological Disease
References	[1]. Kuo CC, et al. Use-dependent inhibition of the N-methyl-D-aspartate currents by felbamate: a gating modifier with selective binding to the desensitized channels. Mol Pharmacol. 2004 Feb;65(2):370-80. [2]. Harty TP, et al. Felbamate block of recombinant N-methyl-D-aspartate receptors: selectivity for the NR2B subunit. Epilepsy Res. 2000 Mar;39(1):47-55.

Description

Felbamate (FBM) is a potent nonsedative anticonvulsant whose clinical effect may be related to the inhibition of N-methyl-D-aspartate (NMDA) .Target: NMDA ReceptorFelbamate (marketed under the brand name Felbatol by MedPointe) is an anti-epileptic 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. However, an increased risk of potentially fatal aplastic anemia and/or liver failure limit the drugs usage to severe refractory epilepsy.Felbamate has been proposed to a unique dual mechanism of action as a positive modulator of GABAA receptors and as a blocker of NMDA receptors, particularly isoforms containing the NR2B subunit. Although it is clear that felbamate does cause pharmacological inhibition of NMDA receptor of relevance of NMDA receptor blockade as a strategy for the treatment of human epilepsy has been questioned. Therefore, the importance of the effects of felbamate on NMDA receptors to its therapeutic action in epilepsy is uncertain.

Related Catalog

Signaling Pathways >>Membrane Transporter/Ion Channel >>iGluRSignaling Pathways >>Neuronal Signaling >>iGluRResearch Areas >>Neurological Disease

References

[1]. Kuo CC, et al. Use-dependent inhibition of the N-methyl-D-aspartate currents by felbamate: a gating modifier with selective binding to the desensitized channels. Mol Pharmacol. 2004 Feb;65(2):370-80.

[2]. Harty TP, et al. Felbamate block of recombinant N-methyl-D-aspartate receptors: selectivity for the NR2B subunit. Epilepsy Res. 2000 Mar;39(1):47-55.

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Boiling Point	511.9±50.0 °C at 760 mmHg
Melting Point	148-1500C
Molecular Formula	C₁₁H₁₄N₂O₄
Molecular Weight	238.240
Flash Point	288.4±26.4 °C
Exact Mass	238.095352
PSA	104.64000
LogP	1.20
Vapour Pressure	0.0±1.3 mmHg at 25°C
Index of Refraction	1.559
InChIKey	WKGXYQFOCVYPAC-UHFFFAOYSA-N
SMILES	NC(=O)OCC(COC(N)=O)c1ccccc1
Storage condition	Store at RT
Water Solubility	alcohol: soluble

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TZ1070000

CHEMICAL NAME :: 1,3-Propanediol, 2-phenyl-, dicarbamate

CAS REGISTRY NUMBER :: 25451-15-4

BEILSTEIN REFERENCE NO. :: 3345236

LAST UPDATED :: 199806

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C11-H14-N2-O4

MOLECULAR WEIGHT :: 238.27

WISWESSER LINE NOTATION :: ZVO1YR&1OVZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 140 mg/kg

TOXIC EFFECTS :: Behavioral - sleep

REFERENCE :: PECAE5 Pediatric Emergency Care. (Williams & Wilkins, 428 E. Preston St., Baltimore, MD 21202) V.1- 1985- Volume(issue)/page/year: 11,369,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 1296 mg/kg/18D-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Gastrointestinal - other changes Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: PHPYDQ Pharmacotherapy (Carlisle, MA). (Pharmacotherapy Pub., Inc., 112 School St., Carlisle, MA 01741) V.1- 1981- Volume(issue)/page/year: 15,260,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 11,931,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 11,931,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 12,462,1969

Safety Information

Symbol	GHS02, GHS06, GHS08
Signal Word	Danger
Hazard Statements	H225-H301 + H311 + H331-H370
Precautionary Statements	P210-P260-P280-P301 + P310-P311
Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR	UN1230 - class 3 - PG 2 - Methanol
WGK Germany	2
RTECS	TZ1070000
HS Code	2924299090

Customs

HS Code	2924299090
Summary	2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles46

Pediatric super-refractory status epilepticus treated with allopregnanolone.

Ann. Neurol. 76(6) , 911-5, (2014)

Super-refractory status epilepticus is a life-threatening condition. Resistance to benzodiazepine and barbiturate treatment for this disorder is thought to be due to internalization of synaptic γ-amin...

Enhanced glutamatergic transmission reduces the anticonvulsant potential of lamotrigine but not of felbamate against tonic-clonic seizures.

Pharmacol. Rep. 59(4) , 462-6, (2007)

The efficacy of lamotrigine and felbamate against maximal electroshock (MES)-induced seizures was assessed under conditions mimicking the pharmacoresistance associated with an increased excitatory neu...

Behavioral and cognitive effects of anti-epileptic drugs.

Discov. Med. 9(45) , 138-44, (2010)

Anti-epileptic drugs (AEDs) have a variety of mechanisms of action which are reflected through different anticonvulsant activities and behavioral effects. Two categories of AEDs are considered based o...

Synonyms

Felbatol

3-propanediol dicarbamate

EINECS 247-001-4

Felbamatum

Felbamato

1,3-Propanediol,2-phenyl-,dicarbamate

1,3-bis-carbamoyloxy-2-phenyl-propane

1,3-Bis-carbamoyloxy-2-phenyl-propan

MFCD00865296

2-Phenyl-1,3-propanediyl dicarbamate

felbamate

Felbamyl

(3-carbamoyloxy-2-phenylpropyl) carbamate

Carbamic acid,2-phenyltrimethylene ester

1,3-Propanediol, 2-phenyl-, dicarbamate

Taloxa

2-Phenylpropane-1,3-diyl dicarbamate

2-phenyl-1,3-propanediol dicarbamate

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