Bromisoval

Bromisoval
Names
	IUPAC name (RS)-2-Bromo-N-carbamoyl-3-methylbutanamide[citation needed]
Identifiers
CAS Number	496-67-3 ; 27109-49-5 R ; 27109-48-4 S ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:31304;
ChEMBL	ChEMBL1515611 ;
ChemSpider	2353 ; 129594 R ; 643139 S ;
ECHA InfoCard	100.007.115
EC Number	207-825-7;
KEGG	D01391;
MeSH	Bromisovalum
PubChem CID	2447; 146955 R; 735997 S;
UNII	469GW8R486 ; 3DY4YGA2PX R ; GTJ4Y0JW4D S ;
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) Key: CMCCHHWTTBEZNM-UHFFFAOYSA-N ;
	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

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.

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.

^ 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. 37 (9). Tokyo, Japan: 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. 36 (10). Tokyo, Japan: 742–746. doi:10.2169/internalmedicine.36.742. PMID 9372340.

[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. 37 (9). Tokyo, Japan: 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. 36 (10). Tokyo, Japan: 742–746. doi:10.2169/internalmedicine.36.742. PMID 9372340.

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