Basic information Safety Supplier Related

Clidinium bromide

Basic information Safety Supplier Related

Clidinium bromide Basic information

Product Name:
Clidinium bromide
Synonyms:
  • CLIDINIUM BROMIDE
  • 3-[(HYDROXYPHENYLACETYL)OXY]-1-METHYL-1-AZONIABICYCLO[2,2,2]OCTANE BROMIDE
  • 3-HYDROXY-1-METHYLQUINUCLIDINIUM BROMIDE BENZILATE
  • QUARZAN
  • RO-2-3773
  • quinuclidinolmethylbromide,benzilate
  • 3-[(Hydroxyphenylacetyl)oxy]-1-methyl-1-azoniabicyclo[2,2,2]octane Bromide, Ro-2-3773, Quarzan
  • Clidinium
CAS:
3485-62-9
MF:
C22H26BrNO3
MW:
432.35
EINECS:
222-471-3
Product Categories:
  • QUARZAN
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
3485-62-9.mol
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Clidinium bromide Chemical Properties

Melting point:
240-241°C
storage temp. 
Inert atmosphere,Room Temperature
form 
neat
CAS DataBase Reference
3485-62-9(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
36
RIDADR 
3249
WGK Germany 
3
RTECS 
VD6125000
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
2933399090
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Clidinium bromide Usage And Synthesis

Chemical Properties

White Crystalline Solid

Originator

Librax,Roche,US,1961

Uses

An anticholinergic. Used as an antispasmodic

Definition

ChEBI: 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 Process

5.12 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 name

Quarzan (Roche).

Therapeutic Function

Anticholinergic, Antiulcer

General Description

Clidinium 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 Use

This 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 bromideSupplier

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