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Identification
NameOxyphenonium
Accession NumberDB00219  (APRD00189)
TypeSmall Molecule
GroupsApproved
DescriptionA 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 CodesA03AB53A03AB03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
1,10-PhenanthrolineThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with 1,10-Phenanthroline.
AclidiniumAclidinium may increase the anticholinergic activities of Oxyphenonium.
AclidiniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Aclidinium.
AlfentanilThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Alfentanil.
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Alphacetylmethadol.
AmbenoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Ambenonium.
Anisotropine MethylbromideThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Anisotropine Methylbromide.
Atracurium besylateThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Atracurium besylate.
AtropineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Atropine.
BenactyzineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Benactyzine.
BendroflumethiazideThe serum concentration of Bendroflumethiazide can be increased when it is combined with Oxyphenonium.
BenzatropineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Benzatropine.
BezitramideThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Bezitramide.
BiperidenThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Biperiden.
Botulinum Toxin Type AOxyphenonium may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BOxyphenonium may increase the anticholinergic activities of Botulinum Toxin Type B.
BuprenorphineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Buprenorphine.
ButorphanolThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Butorphanol.
CarfentanilThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Carfentanil.
ChlorothiazideThe serum concentration of Chlorothiazide can be increased when it is combined with Oxyphenonium.
ChlorphenoxamineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Chlorphenoxamine.
ChlorthalidoneThe serum concentration of Chlorthalidone can be increased when it is combined with Oxyphenonium.
CimetropiumOxyphenonium may increase the anticholinergic activities of Cimetropium.
CodeineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Codeine.
CoumaphosThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Coumaphos.
CyclopentolateThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Cyclopentolate.
DarifenacinThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Darifenacin.
DecamethoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Decamethonium.
DemecariumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Demecarium.
DesloratadineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Desloratadine.
DexetimideThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Dexetimide.
DextromoramideThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Dextromoramide.
DextropropoxypheneThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Dextropropoxyphene.
DezocineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Dezocine.
DichlorvosThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Dichlorvos.
DicyclomineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Dicyclomine.
DihydrocodeineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Dihydrocodeine.
DihydroetorphineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Dihydroetorphine.
DihydromorphineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Dihydromorphine.
DiphenoxylateThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Diphenoxylate.
DonepezilThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Donepezil.
DPDPEThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with DPDPE.
DronabinolOxyphenonium may increase the tachycardic activities of Dronabinol.
EchothiophateThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Echothiophate.
EdrophoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Edrophonium.
EluxadolineOxyphenonium may increase the constipating activities of Eluxadoline.
EthopropazineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Ethopropazine.
EthylmorphineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Ethylmorphine.
EtorphineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Etorphine.
FentanylThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Fentanyl.
FenthionThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Fenthion.
FesoterodineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Fesoterodine.
GalantamineThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Galantamine.
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Gallamine Triethiodide.
Ginkgo bilobaThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Ginkgo biloba.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Glucagon recombinant.
GlycopyrroniumThe risk or severity of adverse effects can be increased when Glycopyrronium is combined with Oxyphenonium.
GlycopyrroniumOxyphenonium may increase the anticholinergic activities of Glycopyrronium.
HeroinThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Heroin.
HexamethoniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Hexamethonium.
HomatropineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Homatropine.
Huperzine AThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Huperzine A.
HydrochlorothiazideThe serum concentration of Hydrochlorothiazide can be increased when it is combined with Oxyphenonium.
HydrocodoneThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Hydrocodone.
HydroflumethiazideThe serum concentration of Hydroflumethiazide can be increased when it is combined with Oxyphenonium.
HydromorphoneThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Hydromorphone.
HyoscyamineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Hyoscyamine.
IndapamideThe serum concentration of Indapamide can be increased when it is combined with Oxyphenonium.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Ipratropium bromide.
IsoflurophateThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Isoflurophate.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Oxyphenonium.
KetobemidoneThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Ketobemidone.
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Levomethadyl Acetate.
LevorphanolThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Levorphanol.
LofentanilThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Lofentanil.
MalathionThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Malathion.
MecamylamineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Mecamylamine.
MefloquineThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Mefloquine.
MemantineThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Memantine.
MethadoneThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Methadone.
Methadyl AcetateThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Methadyl Acetate.
MethanthelineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Methantheline.
MethyclothiazideThe serum concentration of Methyclothiazide can be increased when it is combined with Oxyphenonium.
MetixeneThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Metixene.
MetolazoneThe serum concentration of Metolazone can be increased when it is combined with Oxyphenonium.
MianserinMianserin may increase the anticholinergic activities of Oxyphenonium.
MinaprineThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Minaprine.
MirabegronThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Mirabegron.
MorphineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Morphine.
N-butylscopolammonium bromideThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with N-butylscopolammonium bromide.
NabiloneOxyphenonium may increase the tachycardic activities of Nabilone.
NalbuphineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Nalbuphine.
NeostigmineThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Neostigmine.
NormethadoneThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Normethadone.
NVA237The risk or severity of adverse effects can be increased when Oxyphenonium is combined with NVA237.
OpiumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Opium.
OrphenadrineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Orphenadrine.
OxybutyninThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Oxybutynin.
OxycodoneThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Oxycodone.
OxymorphoneThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Oxymorphone.
PancuroniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Pancuronium.
PentazocineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Pentazocine.
PentoliniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Pentolinium.
PethidineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Pethidine.
PhysostigmineThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Physostigmine.
PipecuroniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Pipecuronium.
PirenzepineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Pirenzepine.
PolythiazideThe serum concentration of Polythiazide can be increased when it is combined with Oxyphenonium.
Potassium ChlorideOxyphenonium may increase the ulcerogenic activities of Potassium Chloride.
PramlintidePramlintide may increase the anticholinergic activities of Oxyphenonium.
ProcyclidineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Procyclidine.
PropanthelineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Propantheline.
PyridostigmineThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Pyridostigmine.
QuinethazoneThe serum concentration of Quinethazone can be increased when it is combined with Oxyphenonium.
QuinidineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Quinidine.
RamosetronOxyphenonium may increase the constipating activities of Ramosetron.
RemifentanilThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Remifentanil.
RivastigmineThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Rivastigmine.
ScopolamineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Scopolamine.
Scopolamine butylbromideThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Scopolamine butylbromide.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Oxyphenonium.
SolifenacinThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Solifenacin.
SufentanilThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Sufentanil.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Oxyphenonium.
TacrineThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Tacrine.
TapentadolThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Tapentadol.
TiotropiumOxyphenonium may increase the anticholinergic activities of Tiotropium.
TiotropiumThe risk or severity of adverse effects can be increased when Tiotropium is combined with Oxyphenonium.
TolterodineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Tolterodine.
TopiramateThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Topiramate.
TramadolThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Tramadol.
TrichlorfonThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Trichlorfon.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Oxyphenonium.
TrihexyphenidylThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Trihexyphenidyl.
TrimethaphanThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Trimethaphan.
TropicamideThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Tropicamide.
TrospiumThe risk or severity of adverse effects can be increased when Trospium is combined with Oxyphenonium.
TubocurarineThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Tubocurarine.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Oxyphenonium.
UmeclidiniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Umeclidinium.
VecuroniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Vecuronium.
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23