Clidinium bromide Chemical Properties
- Melting point:240-241°C
- storage temp. Refrigerator
- form neat
- CAS DataBase Reference3485-62-9(CAS DataBase Reference)
- Language:EnglishProvider:(1-Methyl-1-azoniabicyclo[2.2.2]octan-8-yl) 2-hydroxy-2,2-diphenylacetate bromide
Clidinium bromide Usage And Synthesis
- Chemical PropertiesWhite Crystalline Solid
- UsesAn anticholinergic. Used as an antispasmodic
- DefinitionChEBI: The bromide salt of clinidium. It is used for the symptomatic treatment of peptic ulcer disease and also to help relieve abdominal or stomach spasms or cramps due to colicky abdominal pain, diverticulitis, and irritable bowel syndrome.
- Manufacturing Process5.12 g of 1-azabicyclo[2.2.2]-3-octanol were refluxed with a suspension of
0.92 g of finely divided sodium in 50 cc of toluene, until most of the sodium
had reacted (about 4 hours). The thus obtained suspension of the white
amorphous alcoholate was cooled with ice, and reacted with 10.16 g of
diphenylchloroacetyl chloride, which was added in form of a solution in
approximately 40 cc of toluene. The mixture was stirred for 1 hour at room
temperature. Small amounts of unreacted sodium were destroyed with
isopropanol, and 120 cc of 1 N hydrochloric acid were then added, The
mixture was refluxed for 1/2 hour, in order to convert the first formed
product, diphenylchloroacetic acid ester of 1-azabicyclo[2.2.2]-3-octanol, into
the corresponding benzilic acid ester.
The toluene phase was separated and discarded. The aqueous phase, together with a precipitated water- and toluene-insoluble oil, was made alkaline and extracted repeatedly with chloroform. The chloroform solution was concentrated in vacuo. The residue was recrystallized from a mixture of acetone and ether (alternatively, from chloroform and ether), and formed needles melting at 164° to 165°C. It was identified as 3-benziloyloxy-1- azabicyclo[2.2.2]octane.
3-Benziloyloxy-1-azabicyclo[2.2.2]octane methobromide was prepared by adding 20 cc of a 30% solution of methyl bromide in ether to a solution of 2.5 g of 3-benziloyloxy-1-azabicyclo[2.2.2]octane in 20 cc of chloroform. After standing for 3 hours at room temperature and 15 hours at +5°C, a crystalline precipitate had formed. This was filtered off and recrystallized from a mixture of methanol, acetone, and ether; prisms melting at 240° to 241°C.
- brand nameQuarzan (Roche).
- Therapeutic FunctionAnticholinergic, Antiulcer
- General DescriptionClidinium bromide, 3-hydroxy-1-methylquinuclidinium bromide benzilate (Quarzan),is a white or nearly white, almost odorless, crystalline powderthat is optically inactive. It is soluble in water and alcohol butonly very slightly soluble in ether and benzene.
- Clinical UseThis anticholinergic agent is marketed alone and in combinationwith the minor tranquilizer chlordiazepoxide (Librium)in a product known as Librax. The rationale of the combinationfor the treatment of GI complaints is the use of an anxiety-reducing agent together with an anticholinergic agent,based on the recognized contribution of anxiety to the developmentof the diseased condition. It is suggested for pepticulcer, hyperchlorhydria, ulcerative or spastic colon, anxietystates with GI manifestations, nervous stomach, irritable orspastic colon, and others. Clidinium bromide is contraindicatedin glaucoma and other conditions that may be aggravatedby the parasympatholytic action, such as prostatic hypertrophyin elderly men, which could lead to urinary retention.
- Clidinium bromide Ethidium bromide Thiophanate-methyl tert-Butylchlorodiphenylsilane Rocuronium bromide Bensulfuron methyl Bromide Benzyldodecyldimethylammonium bromide Diphenylsilane Methylparaben Chlorodiphenylphosphine Allyl bromide Diphenylphosphine Benzyl bromide Pipecuronium bromide Parathion-methyl Pinaverium bromide Tiotropium bromide
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