metharbital

{{Short description|Barbiturate anticonvulsant medication}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 459493742

| IUPAC_name = 5,5-Diethyl-1-methylpyrimidine-2,4,6(1H,3H,5H)-trione

| image = Metharbital.svg

| image_class = skin-invert-image

| width = 115

| image2 = Metharbital ball-and-stick.png

| image_class2 = bg-transparent

| width2 = 150

| tradename =

| Drugs.com =

| pregnancy_category =

| legal_CA = Schedule IV

| legal_US = Schedule III

| routes_of_administration = By mouth (tablets)

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| IUPHAR_ligand = 7230

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 50-11-3

| ATC_prefix = N03

| ATC_suffix = AA30

| ATC_supplemental =

| PubChem = 4099

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00463

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 3957

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 02OS7K758T

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01382

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 450

| synonyms = Endiemal, metharbitone, methobarbitone{{cite web | url = http://ctdbase.org/detail.go?type=chem&acc=C084822 | work = The Comparative Toxicogenomics Database | title = Metharbital }}

| C=9 | H=14 | N=2 | O=3

| smiles = O=C1N(C(=O)NC(=O)C1(CC)CC)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C9H14N2O3/c1-4-9(5-2)6(12)10-8(14)11(3)7(9)13/h4-5H2,1-3H3,(H,10,12,14)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FWJKNZONDWOGMI-UHFFFAOYSA-N

}}

Metharbital was patented in 1905 by Emil Fischer working for Merck.{{cite patent | country = US | number = 782742 | title = Trisubstituted barbituric acids and process of making them. | gdate = 14 February 1905 | assign1 = E. Merck | inventor = Fischer E }} It was marketed as Gemonil by Abbott Laboratories. It is a barbiturate anticonvulsant, used in the treatment of epilepsy.{{cite book | title = The Treatment of Epilepsy | edition = 2nd | veditors = Shorvon SR, Fish DR, Perucca E, Dodson WE | publisher = Blackwell | date = 2004 | isbn = 0-632-06046-8 }}{{cite book | title = The Medical Treatment of Epilepsy | vauthors = Resor SR | publisher = Marcel Dekker | date = 1991 | isbn = 0-8247-8549-5 }} It has similar properties to phenobarbital.

History

  • 1952 Gemonil was introduced by Abbott Laboratories.
  • 1990 Abbott stopped marketing.

Synthesis

Metharbital can be synthesized from 2,2-diethylmalonic acid and O-methylisourea.{{cite journal | vauthors = Halpern A, Jones JW | title = The characterization of the trialkylbarbiturates | journal = Journal of the American Pharmaceutical Association | volume = 38 | issue = 6 | pages = 352–5 | date = June 1949 | pmid = 18151714 | doi = 10.1002/jps.3030380619 }}{{Cite journal | vauthors = Snyder JA, Link KP | title = Preparation and Characterization by Alkaline Methanolysis of 5,5-Diethyl-4-(tetraacetyl-β-D-glucosyloxy)-2,6(1,5)-pyrimidinedione | journal = Journal of the American Chemical Society | volume = 75 | issue = 8 | pages = 1881–1883 | year = 1953 | doi = 10.1021/ja01104a030}}

References

{{reflist}}

{{Anticonvulsants}}

{{GABAAR PAMs}}

Category:Anticonvulsants

Category:Barbiturates

Category:Drugs developed by AbbVie

{{anticonvulsant-stub}}