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
Structure for Oxyphenonium (DB00219)
- Weight
- Average: 348.4996
Monoisotopic: 348.253868959 - Chemical Formula
- C21H34NO3
- Synonyms
- Oxyphenonium cation
- Oxyphenonium ion
Pharmacology
- Indication
For the treatment of visceral spasms
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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).
Target Actions Organism AMuscarinic acetylcholine receptor M1 antagonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAclidinium The risk or severity of adverse effects can be increased when Oxyphenonium is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Oxyphenonium is combined with Adenosine. Alfentanil The risk or severity of adverse effects can be increased when Oxyphenonium is combined with Alfentanil. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Oxyphenonium. Amantadine The risk or severity of adverse effects can be increased when Oxyphenonium is combined with Amantadine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Oxyphenonium bromide S9421HWB3Z 50-10-2 UKLQXHUGTKWPSR-UHFFFAOYSA-M - International/Other Brands
- A-Spasm / Antispasmin / Antrenex / Antrenyl / Atrenex / Spasmophen
Categories
- ATC Codes
- A03AB53 — Oxyphenonium, combinations
- A03AB — Synthetic anticholinergics, quaternary ammonium compounds
- A03A — DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
- A03 — DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Agents producing tachycardia
- Alimentary Tract and Metabolism
- Amines
- Anticholinergic Agents
- Autonomic Agents
- Cholinergic Agents
- Drugs for Functional Gastrointestinal Disorders
- Muscarinic Antagonists
- Mydriatics
- Neurotransmitter Agents
- Onium Compounds
- Parasympatholytics
- Peripheral Nervous System Agents
- Quaternary Ammonium Compounds
- Synthetic Anticholinergics, Quaternary Ammonium Compounds
- 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
- External Links
- Human Metabolome Database
- HMDB0014364
- PubChem Compound
- 5749
- PubChem Substance
- 46508840
- ChemSpider
- 5547
- 7818
- ChEBI
- 94329
- ChEMBL
- CHEMBL1201286
- Therapeutic Targets Database
- DAP001124
- PharmGKB
- PA164752252
- Wikipedia
- Oxyphenonium_bromide
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Novartis pharmaceuticals corp
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 191.5 °C PhysProp logP 0.17 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000136 mg/mL ALOGPS logP 0.2 ALOGPS logP -0.2 Chemaxon logS -6.4 ALOGPS pKa (Strongest Acidic) 11.53 Chemaxon pKa (Strongest Basic) -4.3 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.53 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 112.61 m3·mol-1 Chemaxon Polarizability 40.63 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9145 Blood Brain Barrier + 0.9176 Caco-2 permeable + 0.5843 P-glycoprotein substrate Substrate 0.7876 P-glycoprotein inhibitor I Non-inhibitor 0.697 P-glycoprotein inhibitor II Inhibitor 0.6538 Renal organic cation transporter Inhibitor 0.5 CYP450 2C9 substrate Non-substrate 0.8148 CYP450 2D6 substrate Non-substrate 0.8029 CYP450 3A4 substrate Substrate 0.6182 CYP450 1A2 substrate Non-inhibitor 0.7909 CYP450 2C9 inhibitor Non-inhibitor 0.821 CYP450 2D6 inhibitor Inhibitor 0.8189 CYP450 2C19 inhibitor Non-inhibitor 0.7824 CYP450 3A4 inhibitor Non-inhibitor 0.5422 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7636 Ames test Non AMES toxic 0.8956 Carcinogenicity Non-carcinogens 0.7012 Biodegradation Not ready biodegradable 0.7771 Rat acute toxicity 2.7938 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9062 hERG inhibition (predictor II) Inhibitor 0.8391
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-000i-4900000000-e03c3b59b900deeaac2f Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 183.39568 predictedDeepCCS 1.0 (2019) [M+H]+ 185.75368 predictedDeepCCS 1.0 (2019) [M+Na]+ 192.75479 predictedDeepCCS 1.0 (2019)
Targets
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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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:50