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Identification
NameOxyphenonium
Accession NumberDB00219  (APRD00189)
TypeSmall Molecule
GroupsApproved
Description

A quaternary ammonium anticholinergic agent with peripheral side effects similar to those of atropine. It is used as an adjunct in the treatment of gastric and duodenal ulcer, and to relieve visceral spasms. The drug has also been used in the form of eye drops for mydriatic effect. [PubChem]

Structure
Thumb
Synonyms
Oxyphenonium cation
Oxyphenonium ion
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
A-SpasmNot Available
AntispasminNot Available
AntrenexNot Available
AntrenylNot Available
AtrenexNot Available
SpasmophenNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Oxyphenonium bromide
50-10-2
Thumb
  • InChI Key: UKLQXHUGTKWPSR-UHFFFAOYSA-M
  • Monoisotopic Mass: 427.172206606
  • Average Mass: 428.404
DBSALT000207
Categories
UNIID2G5508Y7I
CAS number14214-84-7
WeightAverage: 348.4996
Monoisotopic: 348.253868959
Chemical FormulaC21H34NO3
InChI KeyInChIKey=GFRUPHOKLBPHTQ-UHFFFAOYSA-N
InChI
InChI=1S/C21H34NO3/c1-4-22(3,5-2)16-17-25-20(23)21(24,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6,8-9,12-13,19,24H,4-5,7,10-11,14-17H2,1-3H3/q+1
IUPAC Name
{2-[(2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxy]ethyl}diethylmethylazanium
SMILES
CC[N+](C)(CC)CCOC(=O)C(O)(C1CCCCC1)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Acyl choline
  • Choline
  • Tertiary alcohol
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of visceral spasms
PharmacodynamicsOxyphenonium is an anticholinergic drug, a medication that reduces the effect of acetylcholine, a chemical released from nerves that stimulates muscles, by blocking the receptors for acetylcholine on smooth muscle (a type of muscle). It also has a direct relaxing effect on smooth muscle. Oxyphenonium is used to treat or prevent spasm in the muscles of the gastrointestinal tract in the irritable bowel syndrome. In addition, Oxyphenonium inhibits gastrointestinal propulsive motility and decreases gastric acid secretion and controls excessive pharyngeal, tracheal and bronchial secretions.
Mechanism of actionAction is achieved via a dual mechanism: (1) a specific anticholinergic effect (antimuscarinic) at the acetylcholine-receptor sites and (2) a direct effect upon smooth muscle (musculotropic).
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding93% bound to albumin
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
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-0.9145
Blood Brain Barrier+0.9176
Caco-2 permeable+0.5843
P-glycoprotein substrateSubstrate0.7876
P-glycoprotein inhibitor INon-inhibitor0.697
P-glycoprotein inhibitor IIInhibitor0.6538
Renal organic cation transporterInhibitor0.5
CYP450 2C9 substrateNon-substrate0.8148
CYP450 2D6 substrateNon-substrate0.8029
CYP450 3A4 substrateSubstrate0.6182
CYP450 1A2 substrateNon-inhibitor0.7909
CYP450 2C9 inhibitorNon-inhibitor0.821
CYP450 2D6 inhibitorInhibitor0.8189
CYP450 2C19 inhibitorNon-inhibitor0.7824
CYP450 3A4 inhibitorNon-inhibitor0.5422
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7636
Ames testNon AMES toxic0.8956
CarcinogenicityNon-carcinogens0.7012
BiodegradationNot ready biodegradable0.7771
Rat acute toxicity2.7938 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9062
hERG inhibition (predictor II)Inhibitor0.8391
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point191.5 °CPhysProp
logP0.17Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000136 mg/mLALOGPS
logP0.2ALOGPS
logP-0.2ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)11.53ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity112.61 m3·mol-1ChemAxon
Polarizability40.65 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesA03AB03A03AB53
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
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. Eglen RM, Whiting RL: Competitive and non-competitive antagonism exhibited by 'selective' antagonists at atrial and ileal muscarinic receptor subtypes. Br J Pharmacol. 1987 Apr;90(4):701-7. [PubMed:3580704 ]
  4. 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 May 02, 2016 16:40