3-(carbamoyloxy)-2-phenylpropyl carbamate

• ChemBase ID: 825
• Molecular Formular: C11H14N2O4
• Molecular Mass: 238.23986
• Monoisotopic Mass: 238.09535694
• SMILES: O(CC(c1ccccc1)COC(=O)N)C(=O)N
• Canonical SMILES: NC(=O)OCC(c1ccccc1)COC(=O)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)
• InChIKey: WKGXYQFOCVYPAC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(carbamoyloxy)-2-phenylpropyl carbamate
• IUPAC Traditional name: felbatol; felbamate
• Brand Name: Felbamyl; Felbatol; Taloxa
• Synonyms: 2-Phenyl-1,3-propanedioldicarbamate; Carbamic Acid 2-Phenyltrimethylene Ester; ADD-03055; W-554; Felbamyl; Felbatol; Taloxa; 2-Phenyl-1,3-propanediol dicarbamate; Felbamate; Felbamate; 3-(carbamoyloxy)-2-phenylpropyl carbamate

Database IDs

• CAS Number: 25451-15-4
• EC Number: 247-001-4
• MDL Number: MFCD00865296
• PubChem SID: 46506375; 160964288; 24277968
• PubChem CID: 3331
• CHEBI ID: 4995
• ATC CODE: N03AX10
• CHEMBL: 1094
• Chemspider ID: 3214
• DrugBank ID: DB00949
• KEGG ID: D00536
• Unique Ingredient Identifier: X72RBB02N8
• Wikipedia Title: Felbamate
• Medline Plus: a606011

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.982562
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.67956793
• LogD (pH = 7.4): 0.67956793
• Log P: 0.67956793
• Molar Refractivity: 59.5868 cm^3
• Polarizability: 23.403934 Å^3
• Polar Surface Area: 104.64 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.56
• LOG S: -2.51
• Solubility (Water): 7.42e-01 g/l

PROPERTIES

Physical Property

• Solubility: alcohol: soluble; Dimethyl Sulfoxide; Dimethylformamide; Slightly soluble in water; Water
• Apperance: White Powder
• Melting Point: 148-150°C
• Hydrophobicity(logP): 0.3; 0.497

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: TZ1070000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others
• Admin Routes: Oral
• Bioavailability: > 90%
• Half Life: 20-23 hours
• Metabolism: Hepatic
• Legal Status: Unscheduled
• Pregnancy Category: C (USA)
• Gene Information: human ... GRIN2B(2904)

Product Information

• Purity: 95%
• Salt Data: Free Base

DETAILS

DrugBank - DB00949

• Drug Groups: approved
• 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.
• Indication: For 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.
• Pharmacology: Felbamate 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.
• Toxicity: LD₅₀=5000 mg/kg (Orally in rats)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: >90%
• Half Life: 20-23 hours
• Protein Binding: 20-36%
• Distribution: * 756±82 mL/kg
• Clearance: * 26 +/- 3 mL/hr/kg [single 1200 mg dose]; * 30 +/- 8 mL/hr/kg [multiple daily doses of 3600 mg]
• References: 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: Wikipedia; RxList; Drugs.com

Sigma Aldrich - F0778

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.

Toronto Research Chemicals - F231000

Antiepileptic, structurally similar to meprobamate.

REFERENCES

• 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
• Swinyard, E.A., et al.: Epilepsia, 27, 27 (1986)
• Remmel, R.P., et al.: Ther. Drug Monit., 12, 90 (1986)
• Sofia, R.D., et al.: Epilepsy Res. Suppl., 3, 103 (1986)