Chemistry:Metharbital

From HandWiki
Short description: Barbiturate anticonvulsant medication
Metharbital
Clinical data
Other namesEndiemal, metharbitone, methobarbitone[1]
Routes of
administration
By mouth (tablets)
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC9H14N2O3
Molar mass198.222 g·mol−1
3D model (JSmol)
  (verify)

Metharbital was patented in 1905 by Emil Fischer working for Merck.[2] It was marketed as Gemonil by Abbott Laboratories. It is a barbiturate anticonvulsant, used in the treatment of epilepsy.[3][4] 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.[5][6][2]

References

  1. ↑ "Metharbital". The Comparative Toxicogenomics Database. http://ctdbase.org/detail.go?type=chem&acc=C084822. 
  2. ↑ 2.0 2.1 Fischer E, "Trisubstituted barbituric acids and process of making them.", US patent 782742, issued 14 February 1905, assigned to E. Merck
  3. ↑ The Treatment of Epilepsy (2nd ed.). Blackwell. 2004. ISBN 0-632-06046-8. 
  4. ↑ The Medical Treatment of Epilepsy. Marcel Dekker. 1991. ISBN 0-8247-8549-5. 
  5. ↑ "The characterization of the trialkylbarbiturates". Journal of the American Pharmaceutical Association 38 (6): 352–5. June 1949. doi:10.1002/jps.3030380619. PMID 18151714. 
  6. ↑ "Preparation and Characterization by Alkaline Methanolysis of 5,5-Diethyl-4-(tetraacetyl-β-D-glucosyloxy)-2,6(1,5)-pyrimidinedione". Journal of the American Chemical Society 75 (8): 1881–1883. 1953. doi:10.1021/ja01104a030.