Bromisoval

Last updated
Bromisoval
Bromisoval.svg
Names
IUPAC name
(RS)-2-Bromo-N-carbamoyl-3-methylbutanamide[ citation needed ]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.115 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-825-7
KEGG
MeSH Bromisovalum
PubChem CID
UNII
  • InChI=1S/C6H11BrN2O2/c1-3(2)4(7)5(10)9-6(8)11/h3-4H,1-2H3,(H3,8,9,10,11) Yes check.svgY
    Key: CMCCHHWTTBEZNM-UHFFFAOYSA-N Yes check.svgY
  • CC(C)C(Br)C(=O)NC(N)=O
Properties
C6H11BrN2O2
Molar mass 223.070 g·mol−1
log P 1.057
Acidity (pKa)10.536
Basicity (pKb)3.461
Pharmacology
N05CM03 ( WHO )
Oral
Related compounds
Related ureas
Carbromal
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bromisoval (INN), commonly known as bromovalerylurea, is a hypnotic and sedative of the bromoureide group 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 nonsteroidal anti-inflammatory drugs.

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

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

See also

Related Research Articles

Ataxia is a neurological sign consisting of lack of voluntary coordination of muscle movements that can include gait abnormality, speech changes, and abnormalities in eye movements. Ataxia is a clinical manifestation indicating dysfunction of the parts of the nervous system that coordinate movement, such as the cerebellum. Ataxia can be limited to one side of the body, which is referred to as hemiataxia. Several possible causes exist for these patterns of neurological dysfunction. Dystaxia is a mild degree of ataxia. Friedreich's ataxia has gait abnormality as the most commonly presented symptom. The word is from Greek α- [a negative prefix] + -τάξις [order] = "lack of order".

Nonsteroidal anti-inflammatory drugs (NSAIDs) are members of a drug class that reduces pain, decreases fever, prevents blood clots, and in higher doses, decreases inflammation. Side effects depend on the specific drug but largely include an increased risk of gastrointestinal ulcers and bleeds, heart attack, and kidney disease.

Ibuprofen Medication used for treating pain, fever, and inflammation

Ibuprofen is a medication in the nonsteroidal anti-inflammatory drug (NSAID) class that is used for treating pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. It may also be used to close a patent ductus arteriosus in a premature baby. It can be used by mouth or intravenously. It typically begins working within an hour.

Naproxen A nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, inflammatory diseases such as rheumatoid arthritis, gout, and fever

Naproxen, sold under the brand name Aleve among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, inflammatory diseases such as rheumatoid arthritis, gout and fever. It is taken orally. It is available in immediate and delayed release formulations. Onset of effects is within an hour and last for up to twelve hours.

Meloxicam Nonsteroidal anti-inflammatory drug (NSAID)

Meloxicam, sold under the brand name Mobic among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and inflammation in rheumatic diseases and osteoarthritis. It is used by mouth or by injection into a vein. It is recommended that it be used for as short a period as possible and at a low dose.

Löfgren syndrome Medical condition

Löfgren syndrome is a type of acute sarcoidosis, an inflammatory disorder characterized by swollen lymph nodes in the chest, tender red nodules on the shins, fever and arthritis. It is more common in women than men, and is more frequent in those of Scandinavian, Irish, African and Puerto Rican heritage. It was described in 1953 by Sven Halvar Löfgren, a Swedish clinician. Some have considered the condition to be imprecisely defined.

Oxyphenbutazone

Oxyphenbutazone is a nonsteroidal anti-inflammatory drug (NSAID). It is a metabolite of phenylbutazone.

Spinocerebellar ataxia type 6 Medical condition

Spinocerebellar ataxia type 6 (SCA6) is a rare, late-onset, autosomal dominant disorder, which, like other types of SCA, is characterized by dysarthria, oculomotor disorders, peripheral neuropathy, and ataxia of the gait, stance, and limbs due to cerebellar dysfunction. Unlike other types, SCA 6 is not fatal. This cerebellar function is permanent and progressive, differentiating it from episodic ataxia type 2 (EA2) where said dysfunction is episodic. In some SCA6 families, some members show these classic signs of SCA6 while others show signs more similar to EA2, suggesting that there is some phenotypic overlap between the two disorders. SCA6 is caused by mutations in CACNA1A, a gene encoding a calcium channel α subunit. These mutations tend to be trinucleotide repeats of CAG, leading to the production of mutant proteins containing stretches of 20 or more consecutive glutamine residues; these proteins have an increased tendency to form intracellular agglomerations. Unlike many other polyglutamine expansion disorders expansion length is not a determining factor for the age that symptoms present.

Lymphomatoid granulomatosis is a very rare lymphoproliferative disorder first characterized in 1972. Lymphomatoid means lymphoma-like and granulomatosis denotes the microscopic characteristic of the presence of granulomas with polymorphic lymphoid infiltrates and focal necrosis within it.

Tolmetin

Tolmetin is a nonsteroidal anti-inflammatory drug (NSAID) of the heterocyclic acetic acid derivative class. It is used primarily to reduce hormones that cause pain, swelling, tenderness, and stiffness in conditions such as osteoarthritis and rheumatoid arthritis, including juvenile rheumatoid arthritis. In the United States it is marketed as Tolectin and comes as a tablet or capsule.

Antiganglioside antibodies that react to self-gangliosides are found in autoimmune neuropathies. These antibodies were first found to react with cerebellar cells. These antibodies show highest association with certain forms of Guillain–Barré syndrome.

Meclofenamic acid

Meclofenamic acid is a drug used for joint, muscular pain, arthritis and dysmenorrhea. It is a member of the anthranilic acid derivatives class of nonsteroidal anti-inflammatory drugs (NSAIDs) and was approved by the US FDA in 1980. Like other members of the class, it is a cyclooxygenase (COX) inhibitor, preventing the formation of prostaglandins.

Morniflumate

Morniflumate is a nonsteroidal anti-inflammatory drug (NSAID).

Suplatast tosilate

Suplatast tosilate (INN) is a Th2 cytokine inhibitor which is used as an antiallergic drug. It has been suggested and applied in the treatment of Kimura's disease a few times.

Post-viral cerebellar ataxia also known as acute cerebellitis and acute cerebellar ataxia (ACA) is a disease characterized by the sudden onset of ataxia following a viral infection. The disease affects the function or structure of the cerebellum region in the brain.

Plasma cell granuloma is a lesional pattern of inflammatory pseudotumour, different from the "inflammatory myofibroblastic tumor" pattern.

NSAID or nonsteroidal anti-inflammatory drug hypersensitivity reactions encompasses a broad range of allergic or allergic-like symptoms that occur within minutes to hours after ingesting aspirin or other NSAID nonsteroidal anti-inflammatory drugs. Hypersensitivity drug reactions differ from drug toxicity reactions in that drug toxicity reactions result from the pharmacological action of a drug, are dose-related, and can occur in any treated individual ; hypersensitivity reactions are idiosyncratic reactions to a drug. Although the term NSAID was introduced to signal a comparatively low risk of adverse effects, NSAIDs do evoke a broad range of hypersensitivity syndromes. These syndromes have recently been classified by the European Academy of Allergy and Clinical Immunology Task Force on NSAIDs Hypersensitivity.

Chronic enteropathy associated with SLCO2A1 gene Medical condition

Chronic enteropathy associated with SLCO2A1 gene is a rare autosomal recessive enteropathy that was first described in 1968. This condition was previously named chronic nonspecific multiple ulcers of the small intestine.

Lithium toxicity Medical condition

Lithium toxicity, also known as lithium overdose, is the condition of having too much lithium. Symptoms may include a tremor, increased reflexes, trouble walking, kidney problems, and an altered level of consciousness. Some symptoms may last for a year after levels return to normal. Complications may include serotonin syndrome.

Zaltoprofen

Zaltoprofen is a nonsteroidal anti-inflammatory drug (NSAID) used as an analgesic, antipyretic, and anti-inflammatory agent. It is a selective COX-2 inhibitor and also inhibits bradykinin-induced pain responses without blocking bradykinin receptors.

References

  1. USpatent 914518,Saam, E.,"Alpha-halogen-isovaleryl-urea and process of making the same",issued 1909-03-09, assigned to Knoll
  2. "Bromisoval". International. Drugs.com.
  3. Hashida, H.; Honda, T.; Morimoto, H.; Aibara, Y. (2001). "市販鎮痛剤常用量の服用による慢性ブロム中毒の1例" [A case of chronic bromvalerylurea intoxication due to habitual use of commercially available nonsteroidal anti-inflammatory drugs presenting an indefinite hyperchloremia](pdf). Nihon Ronen Igakkai Zasshi. Japanese Journal of Geriatrics (in Japanese). 38 (5): 700–703. doi: 10.3143/geriatrics.38.700 . ISSN   0300-9173. PMID   11605223.
  4. 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" (pdf). Internal Medicine. Tokyo, Japan. 37 (9): 788–791. doi: 10.2169/internalmedicine.37.788 . PMID   9804091.
  5. 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.
  6. 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" (pdf). Internal Medicine. Tokyo, Japan. 36 (10): 742–746. doi: 10.2169/internalmedicine.36.742 . PMID   9372340.