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

What is the Hydroxy-lacosamide?

The molecule Hydroxy-lacosamide presents a molecular formula of C13H18N2O5 and its IUPAC name is 2-[[(2R)-1-[(4-hydroxyphenyl)methylamino]-3-methoxy-1-oxopropan-2-yl]amino]acetic acid.

Hydroxy-lacosamide is a molecule that is used in the treatment of seizures. It is a derivative of the amino acid glycine and is structurally similar to the neurotransmitter GABA. Hydroxy-lacosamide is thought to act as a selective inhibitor of voltage-gated sodium channels, which are responsible for the generation and propagation of action potentials in neurons. This action prevents seizures by reducing the excitability of neurons. Hydroxy-lacosamide exists as an oral solution and is typically given two to three times daily..

3D structure

Cartesian coordinates

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

2D drawing


Hydroxy-lacosamide RBFMZJMSICTYCA-LLVKDONJSA-N chemical compound 2D structure molecule svg


Molecule descriptors

IUPAC name2-[[(2R)-1-[(4-hydroxyphenyl)methylamino]-3-methoxy-1-oxopropan-2-yl]amino]acetic acid
InChI codeInChI=1S/C13H18N2O5/c1-20-8-11(14-7-12(17)18)13(19)15-6-9-2-4-10(16)5-3-9/h2-5,11,14,16H,6-8H2,1H3,(H,15,19)(H,17,18)/t11-/m1/s1

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.

  • 2-[[(2R)-1-[(4-hydroxyphenyl)methylamino]-3-methoxy-1-oxopropan-2-yl]amino]acetic acid
  • Hydroxy-lacosamide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • CHEBI:174006

Physico-Chemical properties

IUPAC name2-[[(2R)-1-[(4-hydroxyphenyl)methylamino]-3-methoxy-1-oxopropan-2-yl]amino]acetic acid
Molecular formulaC13H18N2O5
Molecular weight282.292
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity70.93
Topological polar surface area107.9

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.