Gabapentin enacarbil, (R)-

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

What is the Gabapentin enacarbil, (R)-?

The molecule Gabapentin enacarbil, (R)- presents a molecular formula of C16H27NO6 and its IUPAC name is 2-[1-[[[(1R)-1-(2-methylpropanoyloxy)ethoxy]carbonylamino]methyl]cyclohexyl]acetic acid.

Gabapentin enacarbil, (R)- is a molecule that is used in the treatment of neuropathic pain and hot flashes. It is a prodrug of gabapentin, and was developed by Pfizer..

Gabapentin enacarbil is structurally similar to the neurotransmitter GABA. It works by binding to the α2δ subunit of voltage-gated calcium channels, which reduces the release of neurotransmitters that are involved in pain signaling..

The FDA approved gabapentin enacarbil in 2011 for the treatment of neuropathic pain in adults. It is also approved for the treatment of hot flashes in menopausal women..

Gabapentin enacarbil is generally well-tolerated. The most common side effects include dizziness, drowsiness, and nausea..

Gabapentin enacarbil is a safe and effective treatment for neuropathic pain and hot flashes. It is generally well-tolerated with few side effects..

3D structure

Cartesian coordinates

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

2D drawing

 

Gabapentin enacarbil, (R)- TZDUHAJSIBHXDL-GFCCVEGCSA-N chemical compound 2D structure molecule svg
Gabapentin enacarbil, (R)-

 

Molecule descriptors

 
IUPAC name2-[1-[[[(1R)-1-(2-methylpropanoyloxy)ethoxy]carbonylamino]methyl]cyclohexyl]acetic acid
InChI codeInChI=1S/C16H27NO6/c1-11(2)14(20)22-12(3)23-15(21)17-10-16(9-13(18)19)7-5-4-6-8-16/h11-12H,4-10H2,1-3H3,(H,17,21)(H,18,19)/t12-/m1/s1
InChI KeyTZDUHAJSIBHXDL-GFCCVEGCSA-N
SMILESCC(C)C(=O)O[C@@H](C)OC(=O)NCC1(CC(=O)O)CCCCC1

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.

  • 1-[[[[(1S)-1-[(2-Methylpropanoyl)oxy]ethoxy]carbonyl]amino]methyl]cyclohexylacetic acid
  • 1-{[(alpha-(R)-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid
  • 1174748-45-8
  • 8TFE968DGA
  • Cyclohexaneacetic acid, 1-(((((1R)-1-(2-methyl-1-oxopropoxy)ethoxy)carbonyl)amino)methyl)-
  • Gabapentin enacarbil, (R)-
  • gabapentin-enacarbil

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1554010
  • UNII-8TFE968DGA
  • SCHEMBL977603

Physico-Chemical properties

IUPAC name2-[1-[[[(1R)-1-(2-methylpropanoyloxy)ethoxy]carbonylamino]methyl]cyclohexyl]acetic acid
Molecular formulaC16H27NO6
Molecular weight329.389
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity84.18
LogP3.1
Topological polar surface area101.9

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.