OXYPHENONIUM

US Previously Marketed

First approved in 1952

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H34NO3
Molecular Weight	348.4996
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

CC[N+](C)(CC)CCOC(=O)C(O)(C1CCCCC1)C2=CC=CC=C2

InChI

InChIKey=GFRUPHOKLBPHTQ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C21H33NO3
Molecular Weight	347.4916
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.druglib.com/activeingredient/oxyphenonium | https://www.ncbi.nlm.nih.gov/pubmed/13396161

Oxyphenonium bromide is a quaternary ammonium anticholinergic agent, which was used under brand name antrenyl, to relieve visceral spasms and as an adjunct in the treatment of peptic ulcer. In addition, Oxyphenonium inhibits gastrointestinal propulsive motility and decreases gastric acid secretion and controls excessive pharyngeal, tracheal and bronchial secretions. Action is achieved via a dual mechanism: a specific anticholinergic effect (antimuscarinic) at the acetylcholine-receptor sites and a direct effect upon smooth muscle. Oxyphenonium bromide also been used in the form of eye drops for mydriatic effec

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor 160 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pubmed/409618	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Visceral spasms 6 Sources: http://www.druglib.com/activeingredient/oxyphenonium/	Primary	Approved 8429	ANTRENYL Approved Use Unknown
Mydriasis 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13396161	Primary	Not Provided 504	Unknown Approved Use Unknown
Peptic ulcer 72 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14371319	Palliative	Approved 8429	ANTRENYL Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
5 ng/mL OTHER https://core.ac.uk/download/pdf/232467634.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		OXYPHENONIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
80 ng/mL OTHER https://core.ac.uk/download/pdf/232467634.pdf	2 mg single, intramuscular dose: 2 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		OXYPHENONIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
0.4 μg × min/mL OTHER https://core.ac.uk/download/pdf/232467634.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYPHENONIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
4.6 μg × min/mL OTHER https://core.ac.uk/download/pdf/232467634.pdf	2 mg single, intramuscular dose: 2 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	OXYPHENONIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
5.9 μg × min/mL OTHER https://core.ac.uk/download/pdf/232467634.pdf	2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered:	OXYPHENONIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
190 min OTHER https://core.ac.uk/download/pdf/232467634.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYPHENONIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
130 min OTHER https://core.ac.uk/download/pdf/232467634.pdf	2 mg single, intramuscular dose: 2 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	OXYPHENONIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2 h OTHER https://core.ac.uk/download/pdf/232467634.pdf	2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered:	OXYPHENONIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
10 mg 3 times / day steady, oral Dose: 10 mg, 3 times / day Route: oral Route: steady Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6329769	unhealthy, 15-29 years n = 8 Health Status: unhealthy Age Group: 15-29 years Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/6329769	Other AEs: Dry mouth... Other AEs: Dry mouth (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/6329769

AEs

AE	Significance	Dose	Population
Dry mouth	3 patients	10 mg 3 times / day steady, oral Dose: 10 mg, 3 times / day Route: oral Route: steady Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6329769	unhealthy, 15-29 years n = 8 Health Status: unhealthy Age Group: 15-29 years Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/6329769

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00DCT0
AAA Chemistry	AR-1D6728
ABI Chem	AC1L1L1W
ABI Chem	AC1Q65RG
AK Scientific	V0895
Asinex	BAS 01095672
BOC Sciences	1407-05-2	https://www.bocsci.com/methocidin-cas-1407-05-2-item-181563.html
Chemspace	CSSS00121581595	https://chem-space.com/CSSS00121581595
Compound Cloud	5748
Compound Cloud	5749
Enamine	EN300-122608
Hairui	HR125629
HongKong Chemhere	18538
IBScreen	STOCK1S-44852
Lab Network	LN00476642
Lab Network	LN01349637
MolPort	MolPort-000-735-345
MuseChem	M055094	https://www.musechem.com/product/M055094.html
NovoSeek	5749
Pharmeks	PHAR048464
Smolecule	S573767	https://www.smolecule.com/products/s573767
THE BioTek	bt-406973	https://www.thebiotek.com/product/others/bt-406973
TimTec	ST095181
Toronto Research Chemicals	O876968
Vitas-M Laboratory	STL325089
ZINC	ZINC000001812122	http://zinc15.docking.org/substances/ZINC000001812122
ZINC	ZINC000001812123	http://zinc15.docking.org/substances/ZINC000001812123
eMolecules	1307688
eMolecules	6324209
mcule	MCULE-3000590480	https://mcule.com/MCULE-3000590480/

PubMed

Title	Date	PubMed
[Software development for calculation of molecular surface area and its application to hydrophobic interaction].	2001 Jan	11201162
Variable effects of previously untested muscarinic receptor antagonists on experimental myopia.	2003 Mar	12601066
Solution structures of 1:1 complexes of oxyphenonium bromide with beta- and gamma-cyclodextrins.	2004 Mar-Apr	15832513
Cyclodextrins in delivery systems: Applications.	2010 Apr	21814436

Patents

Sample Use Guides

In Vivo Use Guide

visceral spasms: oral Mydriasis: oxyphenonium bromide was used as a 5 per cent solution in 1:5,000 benzalconium chloride. Acutely inflamed eyes were treated every 4 hours, the frequency of dosage being reduced as the eye condition improved; post-operative cases were usually treated with twice oxyphenonium bromide 5 per cent drops.

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:11:56 GMT 2023` Edited by `admin` on `Fri Dec 15 16:11:56 GMT 2023`
Record UNII	D2G5508Y7I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXYPHENONIUM

Common Name

English

OXYPHENONIUM [VANDF]

Common Name

English

ETHANAMINIUM, 2-((CYCLOHEXYLHYDROXYPHENYLACETYL)OXY)-N,N-DIETHYL-N-METHYL-

Systematic Name

English

2-(2-CYCLOHEXYL(HYDROXY)PHENYLACETOXY)-N,N-DIETHYL-N-METHYLETHANAMINIUM

Systematic Name

English

ETHANAMINIUM, 2-((2-CYCLOHEXYL-2-HYDROXY-2-PHENYLACETYL)OXY)-N,N-DIETHYL-N-METHYL-

Systematic Name

English

OXYPHENONIUM CATION

Common Name

English

Oxyphenonium [WHO-DD]

Common Name

English

OXYPHENONIUM ION

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA03AB53