| Identification | More | [Name]
Clidinium bromide | [CAS]
3485-62-9 | [Synonyms]
3-HYDROXY-1-METHYLQUINUCLIDINIUM BROMIDE BENZILATE
3-[(HYDROXYPHENYLACETYL)OXY]-1-METHYL-1-AZONIABICYCLO[2,2,2]OCTANE BROMIDE
CLIDINIUM BROMIDE
QUARZAN
RO-2-3773
1-methyl-3-benzil-oxyloxy-quinuclidiniumbromide
3-((hydroxydiphenylacetyl)oxy)-1-methyl-1-azoniabicyclo(2.2.2)octanbromi
3-(2,2-diphenyl-2-hydroxyethanoyloxy)-quinuclidiniumbromide
3-(benziloyloxy)-1-methylquinuclidiniumbromide
benzilicacid,esterwith3-hydroxy-1-methylquinuclidinium
quarzanbromide
quinuclidinium,3-hydroxy-1-methyl-,bromide,benzilate
quinuclidinolmethylbromide,benzilate
3-[(Hydroxyphenylacetyl)oxy]-1-methyl-1-azoniabicyclo[2,2,2]octane Bromide, Ro-2-3773, Quarzan
Clidinium
(1-Methyl-1-azoniabicyclo[2.2.2]octan-8-yl) 2-hydroxy-2,2-diphenylacetate bromide
1-Azoniabicyclo[2.2.2]octane, 3-[(hydroxydiphenylacetyl)oxy]-1-methyl-, bromide
3-[(Hydroxydiphenylacetyl)oxy]-1-methyl-1-azoniabicyclo[2.2.2]octane bromide
Ro-3773
3-[(Hydroxydiphenylacetyl)oxy]-1-methyl-1-azoniabicyclo[2.2.2]octane | [EINECS(EC#)]
222-471-3 | [Molecular Formula]
C22H26BrNO3 | [MDL Number]
MFCD00078996 | [Molecular Weight]
432.35 | [MOL File]
3485-62-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
240-241°C | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly) | [form ]
neat | [color ]
White to Off-White | [Usage]
An anticholinergic. Used as an antispasmodic | [Major Application]
forensics and toxicology
pharmaceutical (small molecule)
veterinary | [InChI]
1S/C22H26NO3.BrH/c1-23-14-12-17(13-15-23)20(16-23)26-21(24)22(25,18-8-4-2-5-9-18)19-10-6-3-7-11-19;/h2-11,17,20,25H,12-16H2,1H3;1H | [InChIKey]
WVDSMJSQJXGCNY-UHFFFAOYSA-N | [SMILES]
Br.C[N]12CCC(CC1)C(C2)OC(=O)C(O)(c3ccccc3)c4ccccc4 | [CAS DataBase Reference]
3485-62-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing . | [RIDADR ]
3249 | [WGK Germany ]
3
| [RTECS ]
VD6125000
| [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
2933399090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Description]
Clidinium is a gastrointestinal muscarinic receptor antagonist (Ki = 3 nM against [3H]quinuclidinyl benzilate binding in rat colonic enterocytes).1 Administration of clidinium, at a dose of 1 mg/kg, slows intestinal transit and induces constipation in mice.2 This clidinium-induced constipation induces serum hyperammonemia and decreases clonic, myoclonic, and tonic seizure thresholds in a murine pentylenetetrazole-induced epilepsy model. | [Chemical Properties]
White Crystalline Solid | [Originator]
Librax,Roche,US,1961 | [Uses]
An anticholinergic. Used as an antispasmodic | [Uses]
An anticholinergic. Used as an antispasmodic. | [Application]
The United States Food and Drug Administration (FDA) approved the use of this combination, clidinium/chlordiazepoxide, as an adjunct therapy for the treatment of peptic ulcer, irritable bowel syndrome (IBS), and acute enterocolitis. | [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. | [Synthesis]
Clidinium, 3-benzyloyloxy-1-methylcynuclidinium bromide (14.1.19), is
synthesized by reacting 3-hydroxycynuclidine (14.1.17) with the of benzilic acid chloride
producing the ester (14.1.18), which if further alkylated at the nitrogen atom by methylbromide, giving clidinium (14.1.19) [16].
| [References]
[1] T W ZIMMERMAN H J B. Muscarinic receptors on rat isolated colonic epithelial cells. A correlation between inhibition of [3H]quinuclidinyl benzilate binding and alteration in ion transport.[J]. Gastroenterology, 1982, 83 6: 1244-1251.
[2] LEILA MOEZI Soroor I Fatema Pirsalami. Constipation enhances the propensity to seizure in pentylenetetrazole-induced seizure models of mice[J]. Epilepsy & Behavior, 2015, 44: Pages 200-206. DOI: 10.1016/j.yebeh.2015.01.013 |
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