Eterobarb

Eterobarb

Clinical data
Routes of administration	Oral
ATC code	none
Identifiers
IUPAC name 5-ethyl-1,3-bis(methoxymethyl)-5-phenyl-1,3-diazinane-2,4,6-trione
CAS Number	27511-99-5^Y
PubChem CID	33925
ChemSpider	31271^N
UNII	432SI047GA
KEGG	D04077^Y
CompTox Dashboard (EPA)	DTXSID9045710
Chemical and physical data
Formula	C16H20N2O5
Molar mass	320.345 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CCC1(C(=O)N(C(=O)N(C1=O)COC)COC)C2=CC=CC=C2
InChI InChI=1S/C16H20N2O5/c1-4-16(12-8-6-5-7-9-12)13(19)17(10-22-2)15(21)18(11-23-3)14(16)20/h5-9H,4,10-11H2,1-3H3^N Key:DACOQFZGGLCXMA-UHFFFAOYSA-N^N
^NY (what is this?)  (verify)

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 can be synthesized by reacting phenobarbital with chloromethyl methyl ether in presence of a base.^[3]

Eterobarb synthesis

References

1. Gallagher BB, Baumel IP, Woodbury SG, Dimicco JA (May 1975). "Clinical evaluation of eterobarb, a new anticonvulsant drug". Neurology. 25 (5): 399–404. doi:10.1212/wnl.25.5.399. PMID 1094318. S2CID 35510833.
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. doi:10.1111/j.1528-1157.1986.tb03518.x. PMID 3956454. S2CID 20206800.
3. Vida JA, Wilber WR, Reinhard JF (March 1971). "Anticonvulsants. 2. Acyloxymethyl and halomethyl derivatives of barbituric acid and diphenylhydantoin". Journal of Medicinal Chemistry. 14 (3): 187–9. doi:10.1021/jm00285a002. PMID 5552206.