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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
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including https://www.ipi-singapore.org/technology-offers/bromvalerylurea-skin-inflammation

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

Sources: DE185962
Curator's Comment: by Knoll in 1907

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Bromisoval

Approved Use

For treatment of insomnia, agitation, chorea, whooping cough
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Inhibition of glutathione S-transferase in rat hepatocytes by a glycine-tetrazole modified S-alkyl-GSH analogue.
2002 Jun 17
Patents

Sample Use Guides

for rats: bromvalerylurea (BROMISOVAL) was subcutaneously administered twice per day
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:20:31 GMT 2023
Edited
by admin
on Fri Dec 15 15:20:31 GMT 2023
Record UNII
469GW8R486
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BROMISOVAL
INN   MART.   WHO-DD  
INN  
Official Name English
BROVARIN
Brand Name English
CALMOTIN
Brand Name English
BROMVALERYLUREA
Common Name English
BROMOVALERYLUREA [JAN]
Common Name English
DIBROLUUR
Brand Name English
.ALPHA.-BROMISOVALERYLUREA
Common Name English
.ALPHA.-BROMOISOVALERIC ACID UREIDE
Common Name English
BROMURAL
Brand Name English
BROMVALETONE
Common Name English
2-BROMO-3-METHYLBUTYRYLUREA
Common Name English
UVALERAL
Brand Name English
.ALPHA.-BROMO-.BETA.-DIMETHYLPROPANOYLUREA
Common Name English
Bromisoval [WHO-DD]
Common Name English
BROMISOVAL [MART.]
Common Name English
BROMISOVALUM [MI]
Common Name English
bromisoval [INN]
Common Name English
BROMISOVALUM
MI  
Common Name English
UPIOL
Brand Name English
BROMOVALERYLUREA
Systematic Name English
DAGRABROMYL
Brand Name English
DORMIGENE
Brand Name English
Classification Tree Code System Code
WHO-ATC N05CM03
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
WHO-VATC QN05CM03
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
NCI_THESAURUS C29756
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
Code System Code Type Description
MESH
D001968
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID2040656
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
FDA UNII
469GW8R486
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
PUBCHEM
2447
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
SMS_ID
100000088677
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
DRUG BANK
DB13370
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-825-7
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
WIKIPEDIA
Bromisoval
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
CHEBI
31304
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL1515611
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
CAS
66101-52-8
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
SUPERSEDED
CAS
496-67-3
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
MERCK INDEX
m2674
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY Merck Index
CAS
12622-72-9
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
SUPERSEDED
CHEBI
77043
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
DRUG CENTRAL
3038
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
NCI_THESAURUS
C76935
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
EVMPD
SUB05916MIG
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
INN
1231
Created by admin on Fri Dec 15 15:20:31 GMT 2023 , Edited by admin on Fri Dec 15 15:20:31 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY