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Oxyphenonium

HCID 5749
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1407-05-2
Standard SMILES
CC[N+](C)(CC)CCOC(=O)C(O)(c1ccccc1)C1CCCCC1
InChIKey
GFRUPHOKLBPHTQ-UHFFFAOYSA-N
Molecular formula
C21H34NO3+
Average molar mass
348.5 g/mol
Monoisotopic mass
348.25386895

Overview

2-(2-cyclohexyl-2-hydroxy-1-oxo-2-phenylethoxy)ethyl-diethyl-methylammonium is an acylcholine.

Names & identifiers

Preferred name
Oxyphenonium
IUPAC
2-(2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxyethyl-diethyl-methylazanium
English name
Oxyphenonium
Molecular formula
C21H34NO3
Molecular weight
348.5

Names & synonyms

oxyphenoniumMethacinOxyphenonium ion14214-84-7Oxyphenonium cationD2G5508Y7IDTXSID80485712-((Cyclohexylhydroxyphenylacetyl)oxy)-N,N-diethyl-N-methylethanaminiumEthanaminium, 2-((cyclohexylhydroxyphenylacetyl)oxy)-N,N-diethyl-N-methyl-{2-[(2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxy]ethyl}diethylmethylazanium(2-((2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxy)ethyl)diethylmethylazaniumIodide, Oxyphenonium
Show more names
2-[Cyclohexyl(hydroxy)(phenyl)acetoxy]-N,N-diethyl-N-methylethanaminiumOxyphenonium free baseDiethylmethyl[2-(hydroxyphenylcyclohexylacetoxy)ethyl]aminiumEthanaminium, 2-[(2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxy]-N,N-diethyl-N-methyl-
Chloride, OxyphenoniumRefChem:169070DTXCID9028203MetacinMethocidinOxiphenonum1407-05-22-(2-cyclohexyl-2-hydroxy-2-phenylacetyl)oxyethyl-diethyl-methylazanium

Properties

Computed structural properties

XLogP
4.1
Topological polar surface area
46.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
9
Heavy atoms
25
Formal charge
1
Complexity
409

Experimental & physicochemical properties

LogP0.17
Solubility1.36e-04 g/L
Human DrugsPharmaceuticals
Melting Point191.5 °C
Physical DescriptionSolid
Collision Cross Section185.7 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

FDA UNII
2 G5508Y7I · D2G5508Y7I

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

oxyphenonium

DILI Negative

DOI:10.1016/j.drudis.2019.09.022

Chemistry & industry

Pharmacology

ATC Code · 2 items

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Protein Binding93% bound to albumin
Pharmacodynamics · 1 item

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 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).
MeSH Pharmacological Classification · 3 items

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics.

Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS.

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system.

Cellular LocationsMembrane

Uses & manufacturing

Use Classification

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
1407-05-2、14214-84-7、50-10-2
PubChem CID
5749
DTXSID
DTXSID8048571
ChEMBL
CHEMBL1201286
ChEBI
CHEBI:94329
UNII
D2G5508Y7I
EC Number
215-801-2
Nikkaji
J14.039B
Pharmaceuticals

Upstream & downstream products

Upstream raw materials

Methyl bromideDiethylaminoethanol

Suppliers1 total

Lanospharma Laboratories Co.,Ltd13440048448 · [email protected]

Additional notes

DefinitionChEBI: 2-(2-cyclohexyl-2-hydroxy-1-oxo-2-phenylethoxy)ethyl-diethyl-methylammonium is an acylcholine.