Metharbital
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| Systematic (IUPAC) name | |
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5,5-Diethyl-1-methylpyrimidine-2,4,6(1H,3H,5H)-trione
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| Clinical data | |
| Routes of administration |
By mouth (tablets) |
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| Identifiers | |
| CAS Number | 50-11-3  |
| ATC code | N03AA30 (WHO) |
| PubChem | CID 4099 |
| IUPHAR/BPS | 7230 |
| DrugBank | DB00463 |
| ChemSpider | 3957 |
| UNII | 02OS7K758T |
| KEGG | D01382 |
| ChEMBL | CHEMBL450 |
| Synonyms | Endiemal, metharbitone, methobarbitone[1] |
| Chemical data | |
| Formula | C9H14N2O3 |
| Molar mass | 198.219 g/mol |
| 3D model (Jmol) | Interactive image |
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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[edit]
- 1952 Gemonil was introduced by Abbott Laboratories.
- 1990 Abbott stopped marketing.
Synthesis[edit]
Metharbital can be synthesized from 2,2-diethylmalonic acid and O-methylisourea.[5][6][7]
References[edit]
- ^ The Comparative Toxicogenomics Database: Metharbital
- ^ US Patent 782742
- ^ The Treatment of Epilepsy 2nd Ed by S. D. Shorvon (Editor), David R. Fish (Editor), Emilio Perucca (Editor), W. Edwin Dodson (Editor). Published by Blackwell 2004. ISBN 0-632-06046-8
- ^ The Medical Treatment of Epilepsy by Stanley R Resor. Published by Marcel Dekker (1991). ISBN 0-8247-8549-5
- ^ A. Halpern, J.W. Jones, J. Am. Pharm. Assoc., 38, 352 (1949)
- ^ Snyder, J. A.; Link, K. P. (1953). "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. doi:10.1021/ja01104a030.
- ^ U.S. Patent 782,742
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