bromisoval

{{chembox

| ImageFile = Bromisoval.svg

| 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.

{{ 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

}} It is marketed over the counter in Asia under various trade names (such as Brovarin {{ cite web | url = https://www.drugs.com/international/bromisoval.html | title = Bromisoval | work = International | publisher = Drugs.com }}), usually in combination with nonsteroidal anti-inflammatory drugs.

Chronic use of bromisoval has been associated with bromine poisoning.{{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

}}{{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

}}{{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

}}{{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

}}

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