Bromisoval

Modify Date: 2024-01-01 18:28:46

Bromisoval Structure
Bromisoval structure
Common Name Bromisoval
CAS Number 496-67-3 Molecular Weight 223.06800
Density 1.504g/cm3 Boiling Point N/A
Molecular Formula C6H11BrN2O2 Melting Point 152 °C
MSDS N/A Flash Point N/A

 Use of Bromisoval


Bromisoval has anti-inflammatory effects and has been used as an old sedative and hypnotic.

 Names

Name 2-bromo-N-carbamoyl-3-methylbutanamide
Synonym More Synonyms

 Bromisoval Biological Activity

Description Bromisoval has anti-inflammatory effects and has been used as an old sedative and hypnotic.
Related Catalog
In Vitro Bromisoval (BU) suppresses nitric oxide (NO) releasing and proinflammatory cytokine expression in lipopolysaccharide (LPS)-treat BV2 cells, a murine microglial cell line. Bromisoval suppresses LPS-inducing phosphorylation of signal transducer and activator of transcription 1 (STAT1) and expression of interferon regulatory factor 1 (IRF1). The Janus kinase 1 (JAK1) inhibitor filgotinib suppresses the NO release much more weakly than that of Bromisoval, although filgotinib almost completely prevents LPS-inducing STAT1 phosphorylation. Knockdown of JAK1, STAT1, or IRF1 does not affect the suppressive effects of Bromisoval on LPS-inducing NO. A combination of Bromisoval and filgotinib synergistically suppress the NO releasing. The mitochondrial complex I inhibitor rotenone, which does not prevent STAT1 phosphorylation or IRF1 expression, suppresses proinflammatory mediator expression less significantly than Bromisoval. Bromisoval and rotenone reduce intracellular ATP (iATP) levels to a similar extent. A combination of rotenone and filgotinib suppress NO release in LPS-treated BV2 cells as strongly as Bromisoval[1].
In Vivo Bromisoval (Bromvaletone) and carbromal are the most potent central depressants within each series. Depressant activities (ISD50 values) and acute toxicities (LD50 values) in male mice after intraperitoneal injection of Bromisoval are 0.35 (0.30-0.39) and 3.25 (2.89-3.62) mmol/kg, respectively[2].
Kinase Assay Conditioning media are obtained from BV2 cell cultures that have been incubated for 24 h in E2 medium containing 1 μg/ml LPS, with or without Bromisoval (BU) (1-100 μg/mL) or other agents, and subjected to NO determination. To normalize the releasing NO level by the cellular protein contents, cells are solubilized with RIPA buffer (50 mM Tris-HCl, pH 8.0, 150 mM sodium chloride, 0.5% w/v sodium deoxycholate, 0.1% w/v sodium dodecyl sulfate, 1.0% w/v NP-40 substitute) and the protein contents are determined by BCA protein assay reagents[1].
Cell Assay Murine microglial cell line BV2 is used. BV2 cells are maintained in medium supplemented with 10% fetal bovine serum. BV2 cells are seeded onto wells in 4-well culture plates and incubated with LPS for 30 min to 24 h. When the effects of Bromisoval (BU) or other agents are investigated, BV2 cells are incubated with the appropriate agent (e.g. Bromisoval) for 30 min before the addition of LPS[1].
Animal Admin Suspensions of the compounds (including Bromisoval ) in aqueous 0.5% carboxymethyl cellulose are administered intraperitoneally to adult male albino mice weighing 25-35 g. All tests are performed on groups of ten mice[2].
References

[1]. Kawasaki S, et al. Effects of hypnotic bromovalerylurea on microglial BV2 cells. J Pharmacol Sci. 2017 Jun;134(2):116-123.

[2]. Mrongovius RI, et al. Comparison of the bromureide sedative-hypnotic drugs, bromvaletone (bromisoval) and carbromal, and their chloro analogues in mice. Clin Exp Pharmacol Physiol. 1976 Sep-Oct;3(5):443-7.

 Chemical & Physical Properties

Density 1.504g/cm3
Melting Point 152 °C
Molecular Formula C6H11BrN2O2
Molecular Weight 223.06800
Exact Mass 222.00000
PSA 72.19000
LogP 1.69200
Index of Refraction 1.514

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YS3150000
CHEMICAL NAME :
Urea, (2-bromo-3-methylbutyryl)-
CAS REGISTRY NUMBER :
496-67-3
BEILSTEIN REFERENCE NO. :
1773255
LAST UPDATED :
199806
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C6-H11-Br-N2-O2
MOLECULAR WEIGHT :
223.10
WISWESSER LINE NOTATION :
ZVMVYEY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
400 mg/kg
TOXIC EFFECTS :
Behavioral - coma Gastrointestinal - nausea or vomiting
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 1,1238,1955
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
57 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. (Toho Daigaku Igakkai, 21-16, Omori-nishi, 5-chome, Ota-ku, Tokyo 143, Japan) V.1- 1954- Volume(issue)/page/year: 7,513,1960
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 7,262,1948
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1340 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1213,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
660 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1213,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
450 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,738,1982
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1289,1935
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
1400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. (Toho Daigaku Igakkai, 21-16, Omori-nishi, 5-chome, Ota-ku, Tokyo 143, Japan) V.1- 1954- Volume(issue)/page/year: 7,513,1960
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Amphibian - frog
DOSE/DURATION :
900 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1289,1935

 Safety Information

Safety Phrases S24/25
RTECS YS3150000
HS Code 2924210090

 Synthetic Route

~%

Bromisoval Structure

Bromisoval

CAS#:496-67-3

Literature: Knoll and Co. Patent: DE275200 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 938

~%

Bromisoval Structure

Bromisoval

CAS#:496-67-3

Literature: Bayer and Co. Patent: DE277466 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 701

~%

Bromisoval Structure

Bromisoval

CAS#:496-67-3

Literature: Fourneau; Florence Bulletin de la Societe Chimique de France, 1927 , vol. <4>41, p. 1525 Full Text Show Details Knoll and Co. Patent: DE185962 ;

~%

Bromisoval Structure

Bromisoval

CAS#:496-67-3

Literature: Knoll and Co. Patent: DE185962 ;

~%

Bromisoval Structure

Bromisoval

CAS#:496-67-3

Literature: Bayer and Co. Patent: DE277466 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 701

 Customs

HS Code 2924210090
Summary 2924210090 other ureines and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

 Synonyms

Alural
EINECS 207-825-7
Bromaral
Bromural
Alluval
Bromoxil
1-(2-Bromoisovaleryl)urea
Abroval
Bromisoval
bromisovalum
Bromovalerylurea
B.V.U.
Bromoval
Bromyl
MFCD00047873
2-Bromo-3-methylbutyrylurea
bromvalerylurea
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