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Details

Stereochemistry RACEMIC
Molecular Formula C6H11BrN2O2
Molecular Weight 223.068
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BROMISOVAL

SMILES

CC(C)C(Br)C(=O)NC(N)=O

InChI

InChIKey=CMCCHHWTTBEZNM-UHFFFAOYSA-N
InChI=1S/C6H11BrN2O2/c1-3(2)4(7)5(10)9-6(8)11/h3-4H,1-2H3,(H3,8,9,10,11)

HIDE SMILES / InChI

Molecular Formula C6H11BrN2O2
Molecular Weight 223.068
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Bromisoval (INN; aka bromvalerylurea) is a hypnotic and sedative compound of the bromoureide group discovered by Knoll in 1907 and patented in 1909. It is marketed over the counter in Asia under various trade names (such as Brovarin) usually in combination with non-steroidal anti-inflammatory drugs. Chronic use of bromisoval has been associated with bromine poisoning. Bromovisal can be prepared by bromination of isovaleric acid by the Hell-Volhard-Zelinsky reaction followed by reaction with urea. Bromvalerylurea (BU) can suppress expression of many kinds of pro- and anti-inflammatory mediators in LPS- or interferon-γ activated alveolar and peritoneal macrophages. Bromisoval was found to ameliorate sepsis in rats. It also prevents elevated serum-IL-6 level as well as IL-6 mRNA expression in septic rats. Bromisoval was also found useful for inflammatory skin disorders. The compound is able to suppress the TLR ligands-induced proinflammatory response similar to the steroid DEX without the side effects often associated with the steroid usage.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Bromisoval
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
for rats: bromvalerylurea (BROMISOVAL) was subcutaneously administered twice per day
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
469GW8R486
Record Status Validated (UNII)
Record Version