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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 of OXYPHENONIUM

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

Description

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

1952
115
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
ANTRENYL

Approved Use

Unknown
Primary
Not Provided
504
Unknown

Approved Use

Unknown
Palliative
Approved
8429
ANTRENYL

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
[Software development for calculation of molecular surface area and its application to hydrophobic interaction].
2001 Jan
Stoichiometric and microenvironmental effects on hydrolysis of propantheline and oxyphenonium bromides in cyclodextrin solutions.
2001 Jun
Variable effects of previously untested muscarinic receptor antagonists on experimental myopia.
2003 Mar
Solution structures of 1:1 complexes of oxyphenonium bromide with beta- and gamma-cyclodextrins.
2004 Mar-Apr
Stability-indicating method for determination of oxyphenonium bromide and its degradation product by high-performance liquid chromatography.
2007 Sep-Oct
Cyclodextrins in delivery systems: Applications.
2010 Apr
Patents

Patents

US8679535
2

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
Name Type Language
OXYPHENONIUM
VANDF   WHO-DD  
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
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
WHO-ATC A03AB53
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
WHO-VATC QA03AB03
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
WHO-ATC A03AB03
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
Code System Code Type Description
DRUG CENTRAL
2039
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY
NCI_THESAURUS
C78076
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY
IUPHAR
7257
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY
MESH
D010115
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY
EVMPD
SUB14736MIG
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY
FDA UNII
D2G5508Y7I
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY
DRUG BANK
DB00219
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY
PUBCHEM
5749
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY
EPA CompTox
DTXSID8048571
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY
SMS_ID
100000079711
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY
WIKIPEDIA
Oxyphenonium
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY
CAS
14214-84-7
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY
RXCUI
7818
Created by admin on Fri Dec 15 16:11:57 UTC 2023 , Edited by admin on Fri Dec 15 16:11:57 UTC 2023
PRIMARY RxNorm
ACTIVE MOIETY
Structure of OXYPHENONIUM
SALT/SOLVATE (PARENT)
Structure of OXYPHENONIUM BROMIDE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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