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

Names
IUPAC name (RS)-2-Bromo-N-carbamoyl-3-methylbutanamide
Identifiers
CAS Number	496-67-3^Y 27109-49-5 R^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:31304
ChEMBL	ChEMBL1515611^Y
ChemSpider	2353^Y 129594 R^Y 643139 S^Y
ECHA InfoCard	100.007.115
EC Number	207-825-7
KEGG	D01391
MeSH	Bromisovalum
PubChem CID	2447 146955 R 735997 S
UNII	469GW8R486^Y
CompTox Dashboard (EPA)	DTXSID2040656
InChI InChI=1S/C6H11BrN2O2/c1-3(2)4(7)5(10)9-6(8)11/h3-4H,1-2H3,(H3,8,9,10,11)^Y Key: CMCCHHWTTBEZNM-UHFFFAOYSA-N^Y
SMILES CC(C)C(Br)C(=O)NC(N)=O
Properties
Chemical formula	C6H11BrN2O2
Molar mass	223.070 g·mol^−1
log P	1.057
Acidity (pKa)	10.536
Basicity (pKb)	3.461
Pharmacology
ATC code	N05CM03 (WHO)
Routes of administration	Oral
Related compounds
Related ureas	Carbromal
Related compounds	3-Ureidopropionic acid beta-Ureidoisobutyric acid Carbamoyl aspartic acid N-Acetylaspartic acid Aceglutamide N-Acetylglutamic acid Citrulline
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

• Acecarbromal
• Carbromal
• Apronal

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.