Bromisoval

Bromisoval

Systematic (IUPAC) name
(RS)-2-bromo-N-carbamoyl-3-methylbutanamide
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	?
Routes	Oral
Identifiers
CAS number	496-67-3^Y
ATC code	N05CM03
PubChem	CID 2447
ChemSpider	2353^Y
UNII	469GW8R486^Y
KEGG	D01391^Y
Chemical data
Formula	C₆H₁₁Br N₂O₂
Mol. mass	223.068 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C6H11BrN2O2/c1-3(2)4(7)5(10)9-6(8)11/h3-4H,1-2H3,(H3,8,9,10,11)^Y Key:CMCCHHWTTBEZNM-UHFFFAOYSA-N^Y
Y(what is this?) (verify)

Bromisoval (INN; commonly known as bromvalerylurea) is a hypnotic and sedative discovered by Knoll in 1907 and patented in 1909.^[1] It is marketed over the counter in Asia under various trade names (such as Brovarin^[2]), usually in combination with non-steroidal anti-inflammatory drugs.

Chronic use of bromisoval has been associated with bromine poisoning.^[3]^[4]^[5]^[6]

References

^ US patent 914518, Saam, Ernst, "Alpha-halogen-isovaleryl-urea and process of making the same", issued 1909-03-09, assigned to Knoll
^ "Bromisoval". International. Drugs.com. http://www.drugs.com/international/bromisoval.html.
^ Hashida, H.; Honda, T.; Morimoto, H.; Aibara, Y. (2001). "A case of chronic bromvalerylurea intoxication due to habitual use of commercially available nonsteroidal anti-inflammatory drugs presenting an indefinite hyperchloremia" (in japanese). Nihon Ronen Igakkai zasshi. Japanese journal of geriatrics 38 (5): 700–703. ISSN 0300-9173. PMID 11605223. http://www.journalarchive.jst.go.jp/english/jnlabstract_en.php?cdjournal=geriatrics1964&cdvol=38&noissue=5&startpage=700. edit
^ Kawakami, T.; Takiyama, Y.; Yanaka, I.; Taguchi, T.; Tanaka, Y.; Nishizawa, M.; Nakano, I. (1998). "Chronic bromvalerylurea intoxication: Dystonic posture and cerebellar ataxia due to nonsteroidal anti-inflammatory drug abuse". Internal medicine (Tokyo, Japan) 37 (9): 788–791. PMID 9804091. http://www.journalarchive.jst.go.jp/jnlpdf.php?cdjournal=internalmedicine1992&cdvol=37&noissue=9&startpage=788&lang=en&from=jnlabstract. edit
^ Wang, Y. -T.; Yang, S. Y.; Wu, V. C.; Wu, K. D.; Fang, C. C. (2005). "Pseudohyperchloraemia due to bromvalerylurea abuse". Nephrology Dialysis Transplantation 20 (8): 1767–1768. doi:10.1093/ndt/gfh945. PMID 15972320. http://ndt.oxfordjournals.org/content/20/8/1767.2.full. edit
^ Arai, A.; Sato, M.; Hozumi, I.; Matsubara, N.; Tanaka, K.; Soma, Y.; Adachi, T.; Tsuji, S. (1997). "Cerebellar ataxia and peripheral neuropathy due to chronic bromvalerylurea poisoning". Internal medicine (Tokyo, Japan) 36 (10): 742–746. PMID 9372340. http://www.journalarchive.jst.go.jp/jnlpdf.php?cdjournal=internalmedicine1992&cdvol=36&noissue=10&startpage=742&lang=en&from=jnlabstract. edit

Hypnotics/Sedatives (N05C)

GABA_A Agonists/PAMs	Barbiturates: Allobarbital • Amobarbital • Aprobarbital • Barbital • Butabarbital • Butobarbital • Cyclobarbital • Ethallobarbital • Heptabarb • Hexobarbital • Mephobarbital • Methohexital • Pentobarbital • Phenobarbital • Proxibarbal • Reposal • Secobarbital • Talbutal • Thiamylal • Thiopental • Vinbarbital • Vinylbital Benzodiazepines: Brotizolam • Clonazepam • Cinolazepam • Climazolam • Doxefazepam • Estazolam • Flunitrazepam • Flurazepam • Flutoprazepam • Haloxazolam • Loprazolam • Lorazepam •Lormetazepam • Midazolam • Nimetazepam • Nitrazepam • Quazepam • Temazepam • Triazolam Carbamates: Carisoprodol • Ethinamate • Hexapropymate • Meprobamate • Methocarbamol • Procymate • Tybamate Neuroactive Steroids: Acebrochol • Allopregnanolone • Alphadolone • Alphaxolone • Eltanolone • Ganaxolone • Hydroxydione • Minaxolone • Org 20599 • Org 21465 • Tetrahydrodeoxycorticosterone Nonbenzodiazepines: CL-218,872 • Eszopiclone • Indiplon • JM-1232 • Lirequinil • Necopidem • Pazinaclone • ROD-188 • Saripidem • Suproclone • Suriclone • SX-3228 • U-89843A • U-90042 • Zaleplon • Zolpidem • Zopiclone Phenols: Fospropofol • Propofol Piperidinediones: Glutethimide • Methyprylon • Pyrithyldione • Piperidione Quinazolinones: Afloqualone • Cloroqualone • Diproqualone • Etaqualone • Mebroqualone • Mecloqualone • Methaqualone • Methylmethaqualone • Nitromethaqualone Volatiles/gases: 2-Methyl-2-butanol • Acetophenone • Acetylglycinamide chloral hydrate • Centalun • Chloral hydrate • Ethanol (Alcohol) • Paraldehyde • Trichloroethanol Others: Bromide (Lithium bromide, Potassium bromide, Sodium bromide) • Chloralose • Chloralodol • Clomethiazole • Dichloralphenazone • Ethchlorvynol • Etomidate • Gaboxadol • Loreclezole • Methylpentynol • Metomidate • Org 25435 • Petrichloral • Sulfonmethane • Triclofos • Valerenic acid (Valerian)

GABA_B Agonists	1,4-Butanediol • Aceburic acid • GABOB • GHB (Sodium oxybate) • GBL • GVL

H₁ Inverse agonists	Antihistamines: Captodiame • Cyproheptadine • Diphenhydramine • Doxylamine • Hydroxyzine • Methapyrilene • Pheniramine • Promethazine • Propiomazine Antidepressants: Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc.) Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.)

α₁-Adrenergic Antagonists	Antidepressants: Serotonin antagonists and reuptake inhibitors (Trazodone) • Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin) Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.) Others: Niaprazine

α₂-Adrenergic Agonists	4-NEMD • Clonidine • Detomidine • Dexmedetomidine • Lofexidine • Medetomidine • Romifidine • Tizanidine • Xylazine

5-HT_2A Antagonists	Antidepressants: Serotonin antagonists and reuptake inhibitors (Trazodone) • Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc.) Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.) Others: Eplivanserin • Niaprazine • Pruvanserin • Volinanserin

Melatonin Agonists	Agomelatine • LY-156,735 • Melatonin • Ramelteon • Tasimelteon

Orexin Antagonists	Almorexant • SB-334,867 • SB-408,124 • SB-649,868 • Suvorexant • TCS-OX2-29

Others	Acecarbromal • Apronal • Bromisoval • Cannabidiol (Cannabis) • Carbromal • Embutramide • Evoxine • Fenadiazole • Gabapentin • Kavalactones (Kava) • Mephenoxalone • Opioids (Oxycodone, Morphine (Opium), etc.) • Passion flower • Scopolamine (Mandrake) • Valnoctamide

Bromisoval

See also

References