Eterobarb

Last updated
Eterobarb
Eterobarb.svg
Clinical data
Routes of
administration
Oral
ATC code
  • none
Identifiers
  • 5-ethyl-1,3-bis(methoxymethyl)-5-phenyl-1,3-diazinane-2,4,6-trione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H20N2O5
Molar mass 320.345 g·mol−1
3D model (JSmol)
  • CCC1(C(=O)N(C(=O)N(C1=O)COC)COC)C2=CC=CC=C2
  • 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 X mark.svgN
  • Key:DACOQFZGGLCXMA-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (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 Eterobarb synthesis.png
Eterobarb synthesis

Related Research Articles

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<span class="mw-page-title-main">Seletracetam</span> Chemical compound

Seletracetam is a pyrrolidone-derived drug of the racetam family that is structurally related to levetiracetam. It was under development by UCB Pharmaceuticals as a more potent and effective anticonvulsant drug to replace levetiracetam but its development has been halted.

<span class="mw-page-title-main">Pipequaline</span> Chemical compound

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<span class="mw-page-title-main">Glaucine</span> Chemical compound

Glaucine(1,2,9,10-TetraMethoxyAporphine, Bromcholitin, Glauvent, Tusidil, Tussiglaucin) is an aporphine alkaloid found in several different plant species in the family Papaveraceae such as Glaucium flavum, Glaucium oxylobum and Corydalis yanhusuo, and in other plants like Croton lechleri in the family Euphorbiaceae.

<span class="mw-page-title-main">Remacemide</span> Chemical compound

Remacemide is a drug which acts as a low-affinity NMDA antagonist with sodium channel blocking properties. It has been studied for the treatment of acute ischemic stroke, epilepsy, Huntington's disease, and Parkinson's disease.

<span class="mw-page-title-main">Barbiturate</span> Class of depressant drugs derived from barbituric acid

Barbiturates are a class of depressant drugs that are chemically derived from barbituric acid. They are effective when used medically as anxiolytics, hypnotics, and anticonvulsants, but have physical and psychological addiction potential as well as overdose potential among other possible adverse effects. They have been used recreationally for their anti-anxiety and sedative effects, and are thus controlled in most countries due to the risks associated with such use.

<span class="mw-page-title-main">Benzobarbital</span> Chemical compound

Benzobarbital (Benzonal) is a barbiturate derivative. It has anticonvulsant effects and has been used for the treatment of epilepsy.

A depressogen is a substance that causes or can cause depression, usually as a side effect. They are the functional opposites of antidepressants.

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.