Felbamate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Felbamate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Felbamate?

The molecule Felbamate presents a molecular formula of C11H14N2O4 and its IUPAC name is (3-carbamoyloxy-2-phenylpropyl) carbamate.

Felbamate is a molecule that is used as an anticonvulsant drug. It is structurally related to the neurotransmitter GABA, and works by inhibiting voltage-gated sodium channels. Felbamate was approved by the FDA in 1993, but was withdrawn from the market in 2006 due to concerns about its potential to cause liver failure..

3D structure

Cartesian coordinates

Geometry of Felbamate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Felbamate WKGXYQFOCVYPAC-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Felbamate

 

Molecule descriptors

 
IUPAC name(3-carbamoyloxy-2-phenylpropyl) carbamate
InChI codeInChI=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)
InChI KeyWKGXYQFOCVYPAC-UHFFFAOYSA-N
SMILESNC(=O)OCC(COC(N)=O)c1ccccc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (3-aminocarbonyloxy-2-phenyl-propyl) carbamate
  • (3-carbamoyloxy-1,1,3,3-tetradeuterio-2-phenylpropyl) carbamate
  • (3-carbamoyloxy-2-phenylpropyl) carbamate
  • 1,3-Propanediol, 2-phenyl-, dicarbamate
  • 2-Phenyl-1,3-propanediol 1,3-dicarbamate
  • 2-Phenyl-1,3-propanediol dicarbamate
  • 2-Phenyl-1,3-propanedioldicarbamate
  • 2-Phenylpropane-1,3-diyl dicarbamate
  • 25451-15-4
  • 3-(carbamoyloxy)-2-phenylpropyl carbamate
  • 451F154
  • A817858
  • AB00382985-18
  • AB00382985_19
  • AC-8197
  • ADD 03055
  • ADD-03055
  • BCP27941
  • BDBM50088430
  • BIDD:GT0463
  • BPBio1_001258
  • BRN 3345236
  • Biomol-NT_000203
  • C07501
  • CCG-204614
  • CS-2068
  • Carbamic acid 3-carbamoyloxy-2-phenyl-propyl ester
  • Carbamic acid, 2-phenyltrimethylene ester
  • D00536
  • DB-046702
  • DB00949
  • DSSTox_CID_3041
  • DSSTox_GSID_23041
  • DSSTox_RID_76847
  • EU-0100524
  • EX-A591
  • F 0778
  • FT-0630517
  • Felbamate
  • Felbamate (USPINN)
  • Felbamate solution
  • Felbamato
  • Felbamatum
  • Felbamyl
  • Felbatol
  • GTPL5473
  • HMS2093P19
  • HMS2234H06
  • HMS3261J09
  • HMS3266L12
  • HMS3370I06
  • HMS3411P21
  • HMS3657I11
  • HMS3675P21
  • HMS3715D20
  • HMS3884E11
  • HSDB 7525
  • HY-B0184
  • KS-1171
  • LP00524
  • Lopac-F-0778
  • Lopac0_000524
  • MFCD00865296
  • MLS000028465
  • MLS001077299
  • NCGC00015429-01
  • NCGC00015429-02
  • NCGC00015429-03
  • NCGC00015429-04
  • NCGC00015429-05
  • NCGC00015429-06
  • NCGC00015429-07
  • NCGC00015429-08
  • NCGC00015429-09
  • NCGC00015429-10
  • NCGC00015429-11
  • NCGC00015429-14
  • NCGC00015429-24
  • NCGC00023092-02
  • NCGC00023092-04
  • NCGC00023092-05
  • NCGC00023092-06
  • NCGC00255275-01
  • NCGC00261209-01
  • NSC 759866
  • NSC-759866
  • NSC759866
  • Opera_ID_1738
  • Pharmakon1600-01505600
  • Prestwick0_000919
  • Q-100326
  • Q421301
  • SBI-0050507.P002
  • SDCCGSBI-0050507.P003
  • SMR000058448
  • SR-01000000089
  • SR-01000000089-2
  • SR-01000000089-4
  • SR-01000000089-7
  • SW197633-2
  • Taloxa
  • Tocris-0869
  • W 554
  • W-554
  • W-554;ADD-03055
  • X72RBB02N8
  • Z1541638522
  • carbamic acid (3-carbamoyloxy-2-phenylpropyl) ester
  • carbamic acid 2-phenyltrimethylene ester
  • felbamate
  • s1330

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1530803
  • CAS-25451-15-4
  • UNII-X72RBB02N8
  • AKOS015895100
  • BRD-K99107520-001-01-9
  • BRD-K99107520-001-09-2
  • BRD-K99107520-001-18-3
  • DTXSID9023041
  • CHEMBL1094
  • CHEBI:4995
  • Tox21_110145
  • Tox21_302368
  • Tox21_500524
  • Tox21_110145_1
  • EINECS 247-001-4
  • SCHEMBL34947

Physico-Chemical properties

IUPAC name(3-carbamoyloxy-2-phenylpropyl) carbamate
Molecular formulaC11H14N2O4
Molecular weight238.24
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity59.40
LogP2.4
Topological polar surface area104.6

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.