Brivaracetam

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

What is the Brivaracetam?

The molecule Brivaracetam presents a molecular formula of C11H20N2O2 and its IUPAC name is (2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl]butanamide.

Brivaracetam (BAN, USAN, trade name Briviact) is an anticonvulsant medication used to treat partial-onset seizures in adults with epilepsy.[1][2] It is also used to treat primary generalized tonic-clonic seizures in adults and children four years of age and older with idiopathic generalized epilepsy.[3][4].

Brivaracetam is a high-affinity SV2A ligand with Ki of 2.3 nM[5] and has shown neuroprotective effects in animal models of global cerebral ischemia,[6] traumatic brain injury,[7] and in an in vitro model of Huntington's disease.[8].

The most common adverse effects include somnolence, dizziness, headache, nausea, and vomiting.[1][2][9] It lies as a pregnancy category C medication, meaning that it may be harmful to a developing fetus.[10].

Brivaracetam was approved for medical use in the United States in 2016,[11] and in the European Union in 2017.[12].

Chemically, brivaracetam is a racetam molecule, with the only difference being a propyl group on the 4-position of the pyrrolidine ring..

3D structure

Cartesian coordinates

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

2D drawing

 

Brivaracetam MSYKRHVOOPPJKU-BDAKNGLRSA-N chemical compound 2D structure molecule svg
Brivaracetam

 

Molecule descriptors

 
IUPAC name(2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl]butanamide
InChI codeInChI=1S/C11H20N2O2/c1-3-5-8-6-10(14)13(7-8)9(4-2)11(12)15/h8-9H,3-7H2,1-2H3,(H2,12,15)/t8-,9+/m1/s1
InChI KeyMSYKRHVOOPPJKU-BDAKNGLRSA-N
SMILESCCC[C@@H]1CC(=O)N([C@@H](CC)C(N)=O)C1

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.

  • (2S)-2-((4R)-2-OXO-4-PROPYLTETRAHYDRO-1H-PYRROL-1-YL) BUTANAMIDE
  • (2S)-2-((4R)-2-Oxo-4-propylpyrrolidin-1-yl)butanamide
  • (2S)-2-((4R)-2-oxo-4-n-propyl-1-pyrrolidinyl)butanamide
  • (2s)-2-[(4r)-2-oxo-4-propylpyrrolidin-1-yl]butanamide
  • (S)-2-((R)-2-Oxo-4-propylpyrrolidin-1-yl)butanamide
  • 1-PYRROLIDINEACETAMIDE, .ALPHA.-ETHYL-2-OXO-4-PROPYL (.ALPHA.S,4R)-
  • 1-Pyrrolidineacetamide, alpha-ethyl-2-oxo-4-propyl-, (alphaS,4R)-
  • 2-(2-oxo-4-propylpyrrolidin-1-yl)butanamide
  • 357336-20-0
  • AC-29289
  • AS-35277
  • BB161996
  • BDBM50422531
  • Brivaracetam
  • Brivaracetam (JAN/USAN/INN)
  • Briviact
  • CCG-266666
  • CS-3418
  • D08879
  • DB05541
  • EX-A2748
  • GTPL9041
  • HY-14449
  • MFCD25976668
  • NCGC00390779-02
  • Q408099
  • Rikelta
  • U863JGG2IA
  • UCB 34714
  • UCB-34714
  • UCB34714
  • compound 83alpha

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3979899
  • UNII-U863JGG2IA
  • AKOS027324306
  • DTXSID00905081
  • CHEMBL607400
  • CHEBI:133013
  • SCHEMBL122081

Physico-Chemical properties

IUPAC name(2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl]butanamide
Molecular formulaC11H20N2O2
Molecular weight212.289
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity62.80
LogP1.5
Topological polar surface area63.4

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.