Oxyphenonium

Identification

Generic Name
Oxyphenonium
DrugBank Accession Number
DB00219
Background

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]

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 348.4996
Monoisotopic: 348.253868959
Chemical Formula
C21H34NO3
Synonyms
  • Oxyphenonium cation
  • Oxyphenonium ion

Pharmacology

Indication

For the treatment of visceral spasms

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Oxyphenonium 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 action

Action 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).

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

93% bound to albumin

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-Benzodiazepine1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Oxyphenonium.
AcetazolamideAcetazolamide may increase the central nervous system depressant (CNS depressant) activities of Oxyphenonium.
AcetophenazineAcetophenazine may increase the central nervous system depressant (CNS depressant) activities of Oxyphenonium.
AclidiniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Oxyphenonium is combined with Adenosine.
AgomelatineAgomelatine may increase the central nervous system depressant (CNS depressant) activities of Oxyphenonium.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Oxyphenonium.
AlimemazineAlimemazine may increase the central nervous system depressant (CNS depressant) activities of Oxyphenonium.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Oxyphenonium.
AlmotriptanAlmotriptan may increase the central nervous system depressant (CNS depressant) activities of Oxyphenonium.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Oxyphenonium bromideS9421HWB3Z50-10-2UKLQXHUGTKWPSR-UHFFFAOYSA-M
International/Other Brands
A-Spasm / Antispasmin / Antrenex / Antrenyl / Atrenex / Spasmophen

Categories

ATC Codes
A03AB53 — Oxyphenonium, combinationsA03AB03 — Oxyphenonium
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
Tetraalkylammonium salts / Tertiary alcohols / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Aromatic alcohols
show 2 more
Substituents
Alcohol / Amine / Aromatic alcohol / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
D2G5508Y7I
CAS number
14214-84-7
InChI Key
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

References

General References
Not Available
Human Metabolome Database
HMDB0014364
PubChem Compound
5749
PubChem Substance
46508840
ChemSpider
5547
RxNav
7818
ChEBI
94329
ChEMBL
CHEMBL1201286
Therapeutic Targets Database
DAP001124
PharmGKB
PA164752252
Wikipedia
Oxyphenonium_bromide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Novartis pharmaceuticals corp
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)191.5 °CPhysProp
logP0.17Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000136 mg/mLALOGPS
logP0.2ALOGPS
logP-0.2ChemAxon
logS-6.4ALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
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...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
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. [Article]
  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. [Article]
  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. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created on June 13, 2005 13:24 / Updated on July 03, 2021 09:19