BROMISOVAL

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 Search

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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/25732089
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

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Insomnia 111 Sources: https://www.rlsnet.ru/mnn_index_id_260.htm https://www.ndrugs.com/?s=bromovalerylurea%20sankei	Primary	Approved 8583	Bromisoval Approved Use For treatment of insomnia, agitation, chorea, whooping cough
Inflammatory skin diseases 5 Sources: https://www.ipi-singapore.org/technology-readiness-level/trl3?page=8	Primary	Basic research	Unknown Approved Use Unknown
Sepsis 74 Sources: http://www.ncbi.nlm.nih.gov/pubmed/25732089	Primary	Basic research	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
14.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12851661/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	DIPHENHYDRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
80.07 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17442639/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMENHYDRINATE plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
47.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2328304/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	DIPHENHYDRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
38.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2328304/	50 mg single, sublingual dose: 50 mg route of administration: Sublingual experiment type: SINGLE co-administered:	DIPHENHYDRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
155.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12851661/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	DIPHENHYDRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
788.43 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17442639/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMENHYDRINATE plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
528 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2328304/	50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered:	DIPHENHYDRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
270 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2328304/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	DIPHENHYDRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
221 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2328304/	50 mg single, sublingual dose: 50 mg route of administration: Sublingual experiment type: SINGLE co-administered:	DIPHENHYDRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
10 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12851661/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	DIPHENHYDRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.44 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17442639/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMENHYDRINATE plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2328304/	50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered:	DIPHENHYDRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2328304/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	DIPHENHYDRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2328304/	50 mg single, sublingual dose: 50 mg route of administration: Sublingual experiment type: SINGLE co-administered:	DIPHENHYDRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B1-00064	http://www.3bsc.com/index/pro_info.php?id=20276
abcr GmbH	AB348961	http://www.abcr.de/shop/en/AB348961
Achemtek	0104-015046	http://www.achemtek.com/523-87-5
AK Scientific, Inc. (AKSCI)	H496	http://www.aksci.com/item_detail.php?cat=H496
AK Scientific, Inc. (AKSCI)	J10430	http://www.aksci.com/item_detail.php?cat=J10430
Alfa Chemistry	AP523875-A	https://reagents.alfa-chemistry.com/product/dimenhydrinate-cas-523-87-5-12502.html
Alfa Chemistry	AP523875-B	https://reagents.alfa-chemistry.com/product/dimenhydrinate-cas-523-87-5-12503.html
Ambeed	A814705	https://www.ambeed.com/products/523-87-5.html
Ambinter	Amb20243141	http://www.ambinter.com/reference/20243141
Aurora Fine Chemicals LLC	A17.876.983	http://online.aurorafinechemicals.com/info?ID=A17.876.983
BLD Pharm	BD21204	http://www.bldpharm.com/products/523-87-5.html
BOC Sciences	523-87-5	https://www.bocsci.com/dramamine-cas-523-87-5-item-344950.html
Boerchem	BC204742	http://www.boerchem.com/?product_34467.html
Chem Scene	CS-4841	http://www.chemscene.com/523-87-5.html
ChemMol	30102262	http://www.chemmol.com/chemmol/30102262.html
ChemMol	44001933	http://www.chemmol.com/chemmol/44001933.html
ChemMol	49402597	http://www.chemmol.com/chemmol/49402597.html
ChemMol	99099684	http://www.chemmol.com/chemmol/99099684.html
Chemspace	CSSB00016999326	https://chem-space.com/CSSB00016999326
Finetech	FT-0625019	http://www.finetechnology-ind.com/prod/detail/pub/523-87-5.html
Finetech	FT-0696921	http://www.finetechnology-ind.com/prod/detail/pub/1030365-02-6.html
Glentham Life Sciences	GP7751	http://www.glentham.com/products/product/GP7751/
Lab Network	LN00222677	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00222677
LGC Standards	LGCFOR0599.00	https://www.lgcstandards.com/US/en/p/LGCFOR0599.00
LGC Standards	MM0599.00	https://www.lgcstandards.com/US/en/p/MM0599.00
MedChem Express	HY-B1215	https://www.medchemexpress.com/Dimenhydrinate.html
MolPort	MolPort-003-666-165	https://www.molport.com/shop/molecule-link/MolPort-003-666-165
MuseChem	I003916	https://www.musechem.com/product/I003916.html
OChem	2474	http://www.ocheminc.com/index.php?act=psearch&pid=523D875
Parchem	28743	http://www.parchem.com/chemical-supplier-distributor/Dimenhydrinate-018743.aspx
Selleck Chemicals	S4672	http://www.selleckchem.com/products/dimenhydrinate.html
Sigma-Aldrich	1206006_USP	https://www.sigmaaldrich.com/catalog/product/usp/1206006?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	D2000000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/d2000000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	D2396_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/d2396?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	PHR1658_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/phr1658?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	Y0001103_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/y0001103?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S526172	http://www.smolecule.com/products/s526172
THE BioTek	bt-265083	https://www.thebiotek.com/product/inhibitors/bt-265083
Yuhao Chemical	LT7774	http://www.chemyuhao.com/523-87-5.html

PubMed

Title	Date	PubMed
Inhibition of glutathione S-transferase in rat hepatocytes by a glycine-tetrazole modified S-alkyl-GSH analogue.	2002-06-17	12039566

Patents

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

Name

Type

Language

BROMISOVAL

Official Name

English

BROMISOVALUM

Preferred 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

UPIOL

Brand Name

English

BROMOVALERYLUREA

Systematic Name

English

DAGRABROMYL

Brand Name

English

DORMIGENE

Brand Name

English

Classification Tree Code System Code

WHO-ATC

N05CM03