Home > Compound List > Compound details
25451-15-4 molecular structure
click picture or here to close

3-(carbamoyloxy)-2-phenylpropyl carbamate

ChemBase ID: 825
Molecular Formular: C11H14N2O4
Molecular Mass: 238.23986
Monoisotopic Mass: 238.09535694
SMILES and InChIs

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

Cite this record

CBID:825 http://www.chembase.cn/molecule-825.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
25451-15-4
EC Number
247-001-4
MDL Number
MFCD00865296
PubChem SID
24277968
46506375
160964288
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.982562  H Acceptors
H Donor LogD (pH = 5.5) 0.67956793 
LogD (pH = 7.4) 0.67956793  Log P 0.67956793 
Molar Refractivity 59.5868 cm3 Polarizability 23.403934 Å3
Polar Surface Area 104.64 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.56  LOG S -2.51 
Solubility (Water) 7.42e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
alcohol: soluble expand Show data source
Dimethyl Sulfoxide expand Show data source
Dimethylformamide expand Show data source
Slightly soluble in water expand Show data source
Water expand Show data source
Apperance
White Powder expand Show data source
Melting Point
148-150°C expand Show data source
Hydrophobicity(logP)
0.3 expand Show data source
0.497 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
TZ1070000 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Target
Others expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
> 90% expand Show data source
Half Life
20-23 hours expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Unscheduled expand Show data source
Pregnancy Category
C (USA) expand Show data source
Gene Information
human ... GRIN2B(2904) expand Show data source
Purity
95% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00949 external link
Item Information
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 external link
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 external link
Antiepileptic, structurally similar to meprobamate.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle