(R)-(-)-Vigabatrin

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

What is the (R)-(-)-Vigabatrin?

The molecule (R)-(-)-Vigabatrin presents a molecular formula of C6H11NO2 and its IUPAC name is (4R)-4-aminohex-5-enoic acid.

Vigabatrin, also known as α-vinyl GABA, is an anticonvulsant and neuroprotective drug. It is used to treat epilepsy and infantile spasms, and has shown promise as a treatment for migraines, depression, and addiction. Vigabatrin is a structural analog of GABA, and works by inhibiting the breakdown of GABA by transaminase enzymes. This leads to increased levels of GABA in the brain, which has a calming effect..

Vigabatrin was first synthesized in 1975, and was approved for use in Europe in 1989. It was approved for use in the United States in 2009. The most common side effects of vigabatrin are dizziness, headache, and nausea. Rare but serious side effects include vision loss and suicidal thoughts..

Vigabatrin is a white powder that is insoluble in water. It is typically supplied as a 500 mg tablet..

3D structure

Cartesian coordinates

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

2D drawing

 

(R)-(-)-Vigabatrin PJDFLNIOAUIZSL-YFKPBYRVSA-N chemical compound 2D structure molecule svg
(R)-(-)-Vigabatrin

 

Molecule descriptors

 
IUPAC name(4R)-4-aminohex-5-enoic acid
InChI codeInChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1
InChI KeyPJDFLNIOAUIZSL-YFKPBYRVSA-N
SMILESC=C[C@H](N)CCC(=O)O

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.

  • (-)-.GAMMA.-VINYL GABA
  • (-)-gamma-Vinyl GABA
  • (4R)-4-aminohex-5-enoic acid
  • (4R)-4-azaniumylhex-5-enoate
  • (R)-(-)-Vigabatrin
  • (R)-4-Aminohex-5-enoic acid
  • (R)-4-Aminohex-5-enoicacid
  • (R)-Vigabatrin
  • 4(R)-AMINO-5-HEXENOIC ACID
  • 5-Hexenoic acid, 4-amino-, (4R)-
  • 77162-51-7
  • BDBM50357219
  • F51879
  • Lopac-V-8261
  • MFCD00274077
  • NCGC00016087-01
  • NCGC00016087-02
  • NCGC00016895-01
  • NCGC00024802-01
  • ODN92S847A
  • Q27285598
  • R(-)-GAMMA-VINYL GABA
  • R-(-)-Vigabatrin
  • R-Vigabatrin
  • RMI 71894
  • RMI-71894
  • Tocris-0808
  • VIGABATRIN, R-(-)-
  • Vigabatrin, (R)-

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC403618
  • CAS-60643-86-9
  • UNII-ODN92S847A
  • DTXSID30227925
  • CHEMBL1361446
  • SCHEMBL9132153

Physico-Chemical properties

IUPAC name(4R)-4-aminohex-5-enoic acid
Molecular formulaC6H11NO2
Molecular weight129.157
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity34.96
LogP1.1
Topological polar surface area63.3

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.