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Identification
NameClidinium
Accession NumberDB00771  (APRD00737)
TypeSmall Molecule
GroupsApproved
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.

Structure
Thumb
Synonyms
3-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-methyl-1-azonia-bicyclo[2.2.2]octane
3-Hydroxy-1-methylquinuclidinium benzilate ester
Bromure de Clidinium
Bromuro de clidinio
Clidinii Bromidum
CLIDINIUM
Clidinium bromid
N-Methyl quinuclidinyl benzilate
External Identifiers
  • Ro 2-3773
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DolibraxRoche
PorsuconYing Yuan
QuarzanRoche
SedaspaHua Shin
Brand mixtures
NameLabellerIngredients
ChloraxAa Pharma Inc
Chlordiazepoxide Hydrochloride and Clidinium BromideAcella Pharmaceuticals, LLC
Chlordiazepoxide Hydrochloride/clidinium BromideAv Kare, Inc.
Corium CapIcn Canada Ltd.
LibraxValeant Pharmaceuticals International
Nu-chlorax Capsules USPNu Pharm Inc
Pro ChloraxPro Doc Limitee
Salts
Name/CASStructureProperties
Clidinium Bromide
ThumbNot applicableDBSALT000958
Categories
UNIIBO76JF850N
CAS number7020-55-5
WeightAverage: 352.4467
Monoisotopic: 352.191268703
Chemical FormulaC22H26NO3
InChI KeyInChIKey=HOOSGZJRQIVJSZ-NNBUQUNQSA-N
InChI
InChI=1S/C22H26NO3/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/q+1/t17-,20?,23+
IUPAC Name
(1s,4s)-3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-1-methyl-1-azabicyclo[2.2.2]octan-1-ium
SMILES
C[N@@+]12CC[C@@H](CC1)C(C2)OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Phenylacetate
  • Quinuclidine
  • Piperidine
  • Tertiary alcohol
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor 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.
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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySigns of toxicity include confusion, paralytic ileus, urinary hesitancy/retention, and blurred vision.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9243
Blood Brain Barrier+0.9142
Caco-2 permeable+0.671
P-glycoprotein substrateSubstrate0.8526
P-glycoprotein inhibitor INon-inhibitor0.7661
P-glycoprotein inhibitor IINon-inhibitor0.9576
Renal organic cation transporterInhibitor0.6314
CYP450 2C9 substrateNon-substrate0.7781
CYP450 2D6 substrateNon-substrate0.6956
CYP450 3A4 substrateSubstrate0.6095
CYP450 1A2 substrateNon-inhibitor0.9528
CYP450 2C9 inhibitorNon-inhibitor0.9459
CYP450 2D6 inhibitorInhibitor0.6154
CYP450 2C19 inhibitorNon-inhibitor0.9577
CYP450 3A4 inhibitorNon-inhibitor0.9504
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9889
Ames testNon AMES toxic0.8557
CarcinogenicityNon-carcinogens0.933
BiodegradationReady biodegradable0.7763
Rat acute toxicity2.4948 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8162
hERG inhibition (predictor II)Non-inhibitor0.6539
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Hoffmann la roche inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral
Prices
Unit descriptionCostUnit
Quarzan 5 mg capsule0.3USD capsule
Quarzan 2.5 mg capsule0.23USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point240-241 °CSternbach, L.H.; US. Patent 2,648,667; August 11,1953; assigned to Hoffmann-LaRoche, Inc.
Predicted Properties
PropertyValueSource
Water Solubility0.000377 mg/mLALOGPS
logP-0.5ALOGPS
logP-1.1ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)11.05ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity112.14 m3·mol-1ChemAxon
Polarizability38.76 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Sternbach, L.H.; US. Patent 2,648,667; August 11,1953; assigned to Hoffmann-LaRoche,
Inc.

General ReferencesNot Available
External Links
ATC CodesA03CA02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AzelastineClidinium may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Clidinium.
BexaroteneThe serum concentration of Clidinium can be decreased when it is combined with Bexarotene.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Clidinium.
CimetropiumClidinium may increase the anticholinergic activities of Cimetropium Bromide.
EluxadolineClidinium may increase the activities of Eluxadoline.
EthanolClidinium may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
FluconazoleThe metabolism of Clidinium can be decreased when combined with Fluconazole.
Fusidic AcidThe serum concentration of Clidinium can be increased when it is combined with Fusidic Acid.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Clidinium.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Clidinium.
MorphineThe risk or severity of adverse effects can be increased when Clidinium is combined with Morphine.
NelfinavirThe metabolism of Clidinium can be decreased when combined with Nelfinavir.
ParoxetineThe risk or severity of adverse effects can be increased when Clidinium is combined with Paroxetine.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Clidinium.
PhenytoinThe metabolism of Clidinium can be increased when combined with Phenytoin.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Clidinium.
RamosetronClidinium may increase the activities of Ramosetron.
St. John's WortThe serum concentration of Clidinium can be decreased when it is combined with St. John's Wort.
TacrineThe therapeutic efficacy of Clidinium can be decreased when used in combination with Tacrine.
TheophyllineThe therapeutic efficacy of Clidinium can be decreased when used in combination with Theophylline.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Clidinium.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Clidinium.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23