3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-1-methyl-1-azabicyclo[2.2.2]octan-1-ium bromide

• ChemBase ID: 651
• Molecular Formular: C22H26BrNO3
• Molecular Mass: 432.35074
• Monoisotopic Mass: 431.1096057
• SMILES: O(C1C2CC[N+](C1)(CC2)C)C(=O)C(O)(c1ccccc1)c1ccccc1.[Br-]
• Canonical SMILES: O=C(C(c1ccccc1)(c1ccccc1)O)OC1C[N+]2(C)CCC1CC2.[Br-]
• InChI: 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/q+1;/p-1
• InChIKey: GKEGFOKQMZHVOW-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-1-methyl-1-azabicyclo[2.2.2]octan-1-ium bromide
• IUPAC Traditional name: clidinium bromide; clidinium bromide bromide
• Brand Name: Quarzan
• Synonyms: Clidinium; 3-[(Hydroxyphenylacetyl)oxy]-1-methyl-1-azoniabicyclo[2,2,2]octane Bromide, Ro-2-3773, Quarzan; Clidinium bromide; 3-Hydroxy-1-methylquinuclidinium bromide benzilate; CLIDINIUM BROMIDE; 可立啶; 克利溴铵

Database IDs

• CAS Number: 7020-55-5; 3485-62-9
• EC Number: 222-471-3
• MDL Number: MFCD00078996
• PubChem SID: 24892253; 160964114
• PubChem CID: 19004

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.047503
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.0832231
• LogD (pH = 7.4): -1.0813938
• Log P: -1.0832465
• Molar Refractivity: 112.1351 cm^3
• Polarizability: 39.71553 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.5
• LOG S: -6.01
• Solubility (Water): 3.77e-04 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 240-241°C

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: VD6125000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Grade: analytical standard

DETAILS

MP Biomedicals - 02154994

(3-Hydroxy-1-methylquinuclidinium bromide benzilate)

DrugBank - DB00771

• Drug Groups: approved
• Description: Clidinium 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. It inhibits muscarinic actions of acetylcholine at postganglionic parasympathetic neuroeffector sites. It is used for the 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.
• Indication: For the 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.
• Pharmacology: Clidinium 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.
• Toxicity: Signs of toxicity include confusion, paralytic ileus, urinary hesitancy/retention, and blurred vision.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - C576250

An anticholinergic. Used as an antispasmodic.

REFERENCES

• Zhang, L., et al.: Pharm. Res., 25, 1902 (2008)
• Sanderson, H., et al.: Toxicol Lett., 187, 84 (2008)