Eterobarb

Eterobarb

Eterobarb
Systematic (IUPAC) name
5-ethyl-1,3-bis(methoxymethyl)-5-phenyl-1,3-diazinane-2,4,6-trione
Clinical data
Legal status
?
Routes Oral
Identifiers
CAS number  YesY
ATC code None
PubChem
ChemSpider  N
UNII  YesY
KEGG  YesY
Chemical data
Formula C16H20N2O5 
Mol. mass 320.340 g/mol
 N   

Eterobarb (Antilon) is a barbiturate derivative. It has mainly anticonvulsant action with less sedative effects than the closely related compound phenobarbital. It saw reasonable success in clinical trials, but is not in widespread medical use.[1][2]

Synthesis

Eterobarb synthesis, Lednicer book 2

Sodium phenobarbital serves as its own base (so the yield is limited to 50%) and reacts readily with "chloro(methoxy)methane" to produce eterobarb.[3]


References

  1. ^ Gallagher, BB; Baumel, IP; Woodbury, SG; Dimicco, JA (1975). "Clinical evaluation of eterobarb, a new anticonvulsant drug". Neurology 25 (5): 399–404.  
  2. ^ Smith, DB; Goldstein, SG; Roomet, A (1986). "A comparison of the toxicity effects of the anticonvulsant eterobarb (antilon, DMMP) and phenobarbital in normal human volunteers". Epilepsia 27 (2): 149–55.  
  3. ^ Vida, Julius A. (1971). "Anticonvulsants. 1. Alkoxymethyl derivatives of barbiturates and diphenylhydantoin". Journal of Medicinal Chemistry 14 (3): 187–189.