eterobarb
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 451553497
| IUPAC_name = 5-ethyl-1,3-bis(methoxymethyl)-5-phenyl-1,3-diazinane-2,4,6-trione
| image = Eterobarb.svg
| width = 175
| tradename =
| pregnancy_category =
| legal_status =
| routes_of_administration = Oral
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 27511-99-5
| ATC_prefix = none
| ATC_suffix =
| PubChem = 33925
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 432SI047GA
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04077
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 31271
| C=16 | H=20 | N=2 | O=5
| smiles = CCC1(C(=O)N(C(=O)N(C1=O)COC)COC)C2=CC=CC=C2
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = DACOQFZGGLCXMA-UHFFFAOYSA-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.{{cite journal | vauthors = Gallagher BB, Baumel IP, Woodbury SG, Dimicco JA | title = Clinical evaluation of eterobarb, a new anticonvulsant drug | journal = Neurology | volume = 25 | issue = 5 | pages = 399–404 | date = May 1975 | pmid = 1094318 | doi = 10.1212/wnl.25.5.399 | s2cid = 35510833 }}{{cite journal | vauthors = Smith DB, Goldstein SG, Roomet A | title = A comparison of the toxicity effects of the anticonvulsant eterobarb (antilon, DMMP) and phenobarbital in normal human volunteers | journal = Epilepsia | volume = 27 | issue = 2 | pages = 149–55 | year = 1986 | pmid = 3956454 | doi = 10.1111/j.1528-1157.1986.tb03518.x | s2cid = 20206800 }}
Synthesis
Eterobarb can be synthesized by reacting phenobarbital with chloromethyl methyl ether in presence of a base.{{cite journal | vauthors = Vida JA, Wilber WR, Reinhard JF | title = Anticonvulsants. 2. Acyloxymethyl and halomethyl derivatives of barbituric acid and diphenylhydantoin | journal = Journal of Medicinal Chemistry | volume = 14 | issue = 3 | pages = 187–9 | date = March 1971 | pmid = 5552206 | doi = 10.1021/jm00285a002 }}
File:Eterobarb synthesis.png{{clear-left}}
References
{{Reflist}}
{{Sedatives}}
{{Anticonvulsants}}
{{GABAAR PAMs}}
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