Clidinium
Basic information
- CAS
7020-55-5- Standard SMILES
C[N+]12CCC(CC1)C(OC(=O)C(O)(c1ccccc1)c1ccccc1)C2- InChIKey
HOOSGZJRQIVJSZ-UHFFFAOYSA-N- Molecular formula
- C22H26NO3+
- Average molar mass
- 352.4 g/mol
- Monoisotopic mass
- 352.19126869
Overview
Clidinium is the ester resulting from formal condensation of benzilic acid and 3-hydroxy-1-methyl-1-azoniabicyclo[2.2.2]octane. It is used, generally as the bromide, 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. It has a role as an anti-arrhythmia drug, a parasympatholytic and an antispasmodic drug. It is an organic cation, a carboxylic ester and a quaternary ammonium ion. It is functionally related to a 3-quinuclidinol and a benzilic acid.
Names & identifiers
- Preferred name
- Clidinium
- IUPAC
- (1-methyl-1-azoniabicyclo[2.2.2]octan-3-yl) 2-hydroxy-2,2-diphenylacetate
- English name
- clidinium
- Molecular formula
- C22H26NO3+
- Molecular weight
- 352.45
Names & synonyms
clidinium7020-55-5N-Methyl quinuclidinyl benzilateClidinium ionClidinium cation3-hydroxy-1-methylquinuclidinium benzilate esterBO76JF850NCHEBI:3743DTXSID60453793-{[hydroxy(diphenyl)acetyl]oxy}-1-methyl-1-azoniabicyclo[2.2.2]octane3-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-methyl-1-azonia-bicyclo[2.2.2]octane3-((hydroxy(diphenyl)acetyl)oxy)-1-methyl-1-azoniabicyclo(2.2.2)octane
Show more names
Clidinium bromide salt13C,2H3]-Clidinium bromide salt3-Hydroxy-1-methylquinuclidinium benzilate (ester)Quinuclidinium, 3-hydroxy-1-methyl-, benzilate (ester)1-Azoniabicyclo(2.2.2)octane, 3-((hydroxydiphenylacetyl)oxy)-1-methyl-
(1-methyl-1-azoniabicyclo(2.2.2)octan-8-yl) 2-hydroxy-2,2-di(phenyl)acetate(1-methyl-1-azoniabicyclo[2.2.2]octan-8-yl) 2-hydroxy-2,2-di(phenyl)acetate3-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-methyl-1-azonia-bicyclo(2.2.2)octaneRefChem:577717DTXCID4025379(1-methyl-1-azoniabicyclo[2.2.2]octan-3-yl) 2-hydroxy-2,2-diphenylacetate[3H]clidiniumUNII-BO76JF850N
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 26
- Formal charge
- 1
- Complexity
- 482
Experimental & physicochemical properties
Human DrugsPharmaceuticals
Melting Point240-241 °C
Collision Cross Section181.98 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- FDA UNII
- 76 JF850N · BO76JF850N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationChemical: 1-Azoniabicyclo[2.2.2]octane, 3-[(hydroxydiphenylacetyl)oxy]-1-methyl-
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Chemistry & industry
Pharmacology
PharmacodynamicsClidinium is a synthetic anticholinergic agent which has been shown in experimental and clinical studies to have a pronounced antispasmodic and antisecretory effect on the gastrointestinal tract.
Mechanism of ActionInhibits muscarinic actions of acetylcholine at postganglionic parasympathetic neuroeffector sites primarily by inhibiting the M1 muscarinic receptors.
FDA Pharmacological Classification
BO76JF850N
CLIDINIUM
Established Pharmacologic Class [EPC] - Anticholinergic
Physiologic Effects [PE] - Decreased Parasympathetic Acetylcholine Activity
Physiologic Effects [PE] - GI Motility Alteration
Physiologic Effects [PE] - Digestive/GI System Activity Alteration
MeSH Pharmacological ClassificationAgents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS.
Uses & manufacturing
Use ClassificationPharmaceuticals
Additional notes
DefinitionChEBI: The ester resulting from formal condensation of benzilic acid and 3-hydroxy-1-methyl-1-azoniabicyclo[2.2.2]octane. It is used, generally as the bromide, for the symptomatic treatment of peptic ulcer disease and also to help relieve abdominal or stomach spa ms or cramps due to colicky abdominal pain, diverticulitis, and irritable bowel syndrome.
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