U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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

Cmax

ValueDoseCo-administeredAnalytePopulation
14.5 ng/mL
25 mg single, oral
DIPHENHYDRAMINE plasma
Homo sapiens
80.07 ng/mL
100 mg single, oral
DIMENHYDRINATE plasma
Homo sapiens
47.8 ng/mL
50 mg single, oral
DIPHENHYDRAMINE plasma
Homo sapiens
38.3 ng/mL
50 mg single, sublingual
DIPHENHYDRAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
155.2 ng × h/mL
25 mg single, oral
DIPHENHYDRAMINE plasma
Homo sapiens
788.43 ng × h/mL
100 mg single, oral
DIMENHYDRINATE plasma
Homo sapiens
528 ng × h/mL
50 mg single, intravenous
DIPHENHYDRAMINE plasma
Homo sapiens
270 ng × h/mL
50 mg single, oral
DIPHENHYDRAMINE plasma
Homo sapiens
221 ng × h/mL
50 mg single, sublingual
DIPHENHYDRAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
25 mg single, oral
DIPHENHYDRAMINE plasma
Homo sapiens
7.44 h
100 mg single, oral
DIMENHYDRINATE plasma
Homo sapiens
4.7 h
50 mg single, intravenous
DIPHENHYDRAMINE plasma
Homo sapiens
5.3 h
50 mg single, oral
DIPHENHYDRAMINE plasma
Homo sapiens
5.4 h
50 mg single, sublingual
DIPHENHYDRAMINE plasma
Homo sapiens

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