Bromisoval

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 nonsteroidal anti-inflammatory drugs.

Bromisoval
Skeletal formula of bromisoval
Names
IUPAC name
(RS)-2-Bromo-N-carbamoyl-3-methylbutanamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.115
EC Number
  • 207-825-7
KEGG
MeSH Bromisovalum
UNII
  • InChI=1S/C6H11BrN2O2/c1-3(2)4(7)5(10)9-6(8)11/h3-4H,1-2H3,(H3,8,9,10,11) checkY
    Key: CMCCHHWTTBEZNM-UHFFFAOYSA-N checkY
  • CC(C)C(Br)C(=O)NC(N)=O
Properties
C6H11BrN2O2
Molar mass 223.070 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

Chronic use of bromisoval has been associated with bromine poisoning.[3][4][5][6]

Bromisoval can be prepared by bromination of isovaleric acid by the Hell-Volhard-Zelinsky reaction followed by reaction with urea.

See also

References
  1. US patent 914518, Saam, E., "Alpha-halogen-isovaleryl-urea and process of making the same", issued 1909-03-09, assigned to Knoll
  2. "Bromisoval". International. Drugs.com.
  3. 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.
  4. 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.
  5. 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.
  6. 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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