Bromisoval
 | |
| Names | |
|---|---|
| IUPAC name
(RS)-2-Bromo-N-carbamoyl-3-methylbutanamide | |
| Identifiers | |
496-67-3  27109-49-5 R | |
| ChEBI | CHEBI:31304 |
| ChEMBL | ChEMBL1515611 |
| ChemSpider | 2353 129594 R 643139 S |
| EC Number | 207-825-7 |
| Jmol 3D model | Interactive image Interactive image |
| KEGG | D01391 |
| MeSH | Bromisovalum |
| PubChem | 2447 146955 R 735997 S |
| UNII | 469GW8R486 |
| |
| |
| Properties | |
| C6H11BrN2O2 | |
| Molar mass | 223.07 g·mol−1 |
| log P | 1.057 |
| Acidity (pKa) | 10.536 |
| Basicity (pKb) | 3.461 |
| Pharmacology | |
| N05CM03 (WHO) | |
| Oral | |
| Related compounds | |
| Related ureas |
Carbromal |
| Related compounds |
|
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Bromisoval (INN), commonly known as bromovalerylurea, is a hypnotic and sedative of the bromoureide group discovered by Knoll in 1907 and patented in 1909.[1] It is marketed over the counter in Asia under various trade names (such as Brovarin[2]), usually in combination with non-steroidal anti-inflammatory drugs.
Chronic use of bromisoval has been associated with bromine poisoning.[3][4][5][6]
Bromovisal can be prepared by bromination of isovaleric acid by the Hell-Volhard-Zelinsky reaction followed by reaction with urea.
See also
References
- ↑ US patent 914518, Saam, E., "Alpha-halogen-isovaleryl-urea and process of making the same", issued 1909-03-09, assigned to Knoll
- ↑ "Bromisoval". International. Drugs.com.
- ↑ Hashida, H.; Honda, T.; Morimoto, H.; Aibara, Y. (2001). "市販鎮痛剤常用量の服用による慢性ブロム中毒の1例" [A case of chronic bromvalerylurea intoxication due to habitual use of commercially available nonsteroidal anti-inflammatory drugs presenting an indefinite hyperchloremia] (pdf). Nihon Ronen Igakkai Zasshi. Japanese Journal of Geriatrics (in Japanese) 38 (5): 700–703. doi:10.3143/geriatrics.38.700. ISSN 0300-9173. PMID 11605223.
- ↑ Kawakami, T.; Takiyama, Y.; Yanaka, I.; Taguchi, T.; Tanaka, Y.; Nishizawa, M.; Nakano, I. (1998). "Chronic bromvalerylurea intoxication: Dystonic posture and cerebellar ataxia due to nonsteroidal anti-inflammatory drug abuse" (pdf). Internal Medicine (Tokyo, Japan) 37 (9): 788–791. doi:10.2169/internalmedicine.37.788. PMID 9804091.
- ↑ Wang, Y. -T.; Yang, S. Y.; Wu, V. C.; Wu, K. D.; Fang, C. C. (2005). "Pseudohyperchloraemia due to bromvalerylurea abuse". Nephrology Dialysis Transplantation 20 (8): 1767–1768. doi:10.1093/ndt/gfh945. PMID 15972320.
- ↑ Arai, A.; Sato, M.; Hozumi, I.; Matsubara, N.; Tanaka, K.; Soma, Y.; Adachi, T.; Tsuji, S. (1997). "Cerebellar Ataxia and Peripheral Neuropathy due to Chronic Bromvalerylurea Poisoning" (pdf). Internal Medicine (Tokyo, Japan) 36 (10): 742–746. doi:10.2169/internalmedicine.36.742. PMID 9372340.
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