Bromisoval

{{chembox | ImageFile = Bromisoval.svg | ImageClass = skin-invert-image | ImageFile_Ref = {{chemboximage|correct|??}} | ImageName = Skeletal formula of bromisoval | IUPACName = (''RS'')-2-Bromo-''N''-carbamoyl-3-methylbutanamide{{citation needed|date=May 2012}} |Section1={{Chembox Identifiers | CASNo = 496-67-3 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo1 = 27109-49-5 | CASNo1_Ref = {{cascite|correct|CAS}} | CASNo1_Comment = ''R'' | CASNo2 = 27109-48-4 | CASNo2_Ref = {{cascite|correct|CAS}} | CASNo2_Comment = ''S'' | PubChem = 2447 | PubChem1 = 146955 | PubChem1_Comment = ''R'' | PubChem2 = 735997 | PubChem2_Comment = ''S'' | ChemSpiderID = 2353 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID1 = 129594 | ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID1_Comment = ''R'' | ChemSpiderID2 = 643139 | ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID2_Comment = ''S'' | UNII = 469GW8R486 | UNII_Ref = {{fdacite|correct|FDA}} | UNII1_Ref = {{fdacite|correct|FDA}} | UNII1 = 3DY4YGA2PX | UNII1_Comment = ''R'' | UNII2_Ref = {{fdacite|correct|FDA}} | UNII2 = GTJ4Y0JW4D | UNII2_Comment = ''S'' | EINECS = 207-825-7 | KEGG = D01391 | MeSHName = Bromisovalum | ChEBI = 31304 | ChEMBL = 1515611 | ChEMBL_Ref = {{ebicite|correct|EBI}}

| SMILES = CC(C)C(Br)C(=O)NC(N)=O | StdInChI = 1S/C6H11BrN2O2/c1-3(2)4(7)5(10)9-6(8)11/h3-4H,1-2H3,(H3,8,9,10,11) | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = CMCCHHWTTBEZNM-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} |Section2={{Chembox Properties | C=6 | H=11 | Br=1 | N=2 | O=2 | LogP = 1.057 | pKa = 10.536 | pKb = 3.461 }} |Section6={{Chembox Pharmacology | ATCCode_prefix = N05 | ATCCode_suffix = CM03 | AdminRoutes = Oral }} |Section8={{Chembox Related | OtherFunction_label = ureas | OtherFunction = Carbromal | OtherCompounds = {{unbulleted list|3-Ureidopropionic acid|''beta''-Ureidoisobutyric acid|Carbamoyl aspartic acid|''N''-Acetylaspartic acid|Aceglutamide|''N''-Acetylglutamic acid|Citrulline}} }} }}

'''Bromisoval''' (INN), commonly known as '''bromovalerylurea''', is a hypnotic and sedative of the bromoureide group discovered by Knoll in 1907 and patented in 1909.<ref> {{ cite patent | country = US | status = patent | number = 914518 | gdate = 1909-03-09 | invent1 = Saam, E. | assign1 = Knoll | pridate = 1907-01-28 | title = Alpha-halogen-isovaleryl-urea and process of making the same }}</ref> It is marketed over the counter in Asia under various trade names (such as ''Brovarin''<ref> {{ cite web | url = https://www.drugs.com/international/bromisoval.html | title = Bromisoval | work = International | publisher = Drugs.com }}</ref>), usually in combination with nonsteroidal anti-inflammatory drugs.

Chronic use of bromisoval has been associated with bromine poisoning.<ref>{{Cite journal | last1 = Hashida | first1 = H. | last2 = Honda | first2 = T. | last3 = Morimoto | first3 = H. | last4 = Aibara | first4 = Y. | title = 市販鎮痛剤常用量の服用による慢性ブロム中毒の1例 |trans-title=A case of chronic bromvalerylurea intoxication due to habitual use of commercially available nonsteroidal anti-inflammatory drugs presenting an indefinite hyperchloremia | journal = Nihon Ronen Igakkai Zasshi. Japanese Journal of Geriatrics | volume = 38 | language = Japanese | issue = 5 | pages = 700–703 | year = 2001 | pmid = 11605223 | issn = 0300-9173 | doi = 10.3143/geriatrics.38.700 | url = http://www.jstage.jst.go.jp/article/geriatrics1964/38/5/38_5_700/_pdf | format = pdf | doi-access = free }}</ref><ref>{{Cite journal | last1 = Kawakami | first1 = T. | last2 = Takiyama | first2 = Y. | last3 = Yanaka | first3 = I. | last4 = Taguchi | first4 = T. | last5 = Tanaka | first5 = Y. | last6 = Nishizawa | first6 = M. | last7 = Nakano | first7 = I. | title = Chronic bromvalerylurea intoxication: Dystonic posture and cerebellar ataxia due to nonsteroidal anti-inflammatory drug abuse | journal = Internal Medicine | location = Tokyo, Japan | volume = 37 | issue = 9 | pages = 788–791 | year = 1998 | pmid = 9804091 | doi = 10.2169/internalmedicine.37.788 | url = http://www.jstage.jst.go.jp/article/internalmedicine1992/37/9/37_9_788/_pdf | format = pdf | doi-access = free }}</ref><ref>{{Cite journal | last1 = Wang | first1 = Y. -T. | last2 = Yang | first2 = S. Y. | last3 = Wu | first3 = V. C. | last4 = Wu | first4 = K. D. | last5 = Fang | first5 = C. C. | title = Pseudohyperchloraemia due to bromvalerylurea abuse | doi = 10.1093/ndt/gfh945 | journal = Nephrology Dialysis Transplantation | volume = 20 | issue = 8 | pages = 1767–1768 | year = 2005 | pmid = 15972320 | pmc = | doi-access = free }}</ref><ref>{{Cite journal | last1 = Arai | first1 = A. | last2 = Sato | first2 = M. | last3 = Hozumi | first3 = I. | last4 = Matsubara | first4 = N. | last5 = Tanaka | first5 = K. | last6 = Soma | first6 = Y. | last7 = Adachi | first7 = T. | last8 = Tsuji | first8 = S. | title = Cerebellar Ataxia and Peripheral Neuropathy due to Chronic Bromvalerylurea Poisoning | journal = Internal Medicine | location = Tokyo, Japan | volume = 36 | issue = 10 | pages = 742–746 | year = 1997 | pmid = 9372340 | doi = 10.2169/internalmedicine.36.742 | url = http://www.jstage.jst.go.jp/article/internalmedicine1992/36/10/36_10_742/_pdf | format = pdf | doi-access = free }}</ref>

Bromisoval can be prepared by bromination of isovaleric acid by the Hell-Volhard-Zelinsky reaction followed by reaction with urea.

==See also== * Acecarbromal * Carbromal * Apronal

==References== {{Reflist|2}}

Category:Hypnotics Category:Sedatives Category:Organobromides Category:GABAA receptor positive allosteric modulators