Quinoxalinedione

Quinoxalinedione is an organic compound with the formula C6H4(NH)2(CO)2. It is a colorless solid that is soluble in polar organic solvents. Quinoxalinediones are a family of related compounds sharing the same bicyclic core. Various quinoxalinediones are drugs.

Synthesis and structure
Quinoxalinedione is produced by condensation of dimethyloxalate and o-phenylenediamine:
 * C2O2(OMe)2 +  C6H4(NH2)2   →   C6H4(NH)2(CO)2  +  2 MeOH

The compound exists in solution and the solid state predominantly as the diamide form. Some reactions of the compound indicate a role for the diol tautomer.

Drugs based on quinoxalinediones
Quinoxalinediones act as antagonists of the AMPA, kainate, and/or NMDA receptors of the ionotropic glutamate receptor family. Examples include the following:


 * ACEA-1011
 * Becampanel
 * CNQX
 * DNQX
 * Fanapanel (MPQX)
 * Licostinel (ACEA-1021)
 * NBQX
 * PNQX
 * YM90K
 * Zonampanel

A drug closely related to the quinoxalinediones, but possessing a quinazoline-2,4-dione structure instead, is selurampanel. Caroverine is another closely related drug to the above, but instead containing a quinoxaline-2-one structure.