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Details

Stereochemistry RACEMIC
Molecular Formula C21H34NO3.Br
Molecular Weight 428.404
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYPHENONIUM BROMIDE

SMILES

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

InChI

InChIKey=UKLQXHUGTKWPSR-UHFFFAOYSA-M
InChI=1S/C21H34NO3.BrH/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;1H/q+1;/p-1

HIDE SMILES / InChI
Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:14:31 UTC 2023
Edited
by admin
on Fri Dec 15 15:14:31 UTC 2023
Record UNII
S9421HWB3Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXYPHENONIUM BROMIDE
INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
ANTRENIL
Brand Name English
OXYFENON
Brand Name English
oxyphenonium bromide [INN]
Common Name English
OXYPHENONIUM BROMIDE [VANDF]
Common Name English
OXYPHENON
Brand Name English
SPASMODIN
Brand Name English
C-5473
Code English
ETHANAMINIUM, 2-((2-CYCLOHEXYL-2-HYDROXY-2-PHENYLACETYL)OXY)-N,N-DIETHYL-N-METHYL-, BROMIDE (1:1)
Systematic Name English
ETHANAMINIUM, 2-((CYCLOHEXYLHYDROXYPHENYLACETYL)OXY)-N,N-DIETHYL-N-METHYL-, BROMIDE
Systematic Name English
NSC-759248
Code English
OXYPHENONIUM BROMIDE [MI]
Common Name English
OXIFENON
Brand Name English
Oxyphenonium bromide [WHO-DD]
Common Name English
SPASMOPHEN
Brand Name English
OXYPHENONIUM BROMIDE [MART.]
Common Name English
OXYPHENONIUM BROMIDE [ORANGE BOOK]
Common Name English
BA-5473
Code English
ANTRENYL
Brand Name English
(±)-OXYPHENONIUM BROMIDE
Common Name English
DIETHYL(2-HYDROXYETHYL)METHYLAMMONIUM BROMIDE .ALPHA.-PHENYLCYCLOHEXANEGLYCOLATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
NCI_THESAURUS C29698
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C66285
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
SMS_ID
100000092146
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
CAS
50-10-2
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-010-7
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
RXCUI
42833
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1201286
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
DRUG BANK
DB00219
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
EPA CompTox
DTXSID4045632
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
MERCK INDEX
m8344
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY Merck Index
PUBCHEM
5748
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
NSC
759248
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
EVMPD
SUB09575MIG
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
INN
20
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
WIKIPEDIA
OXYPHENONIUM BROMIDE
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
FDA UNII
S9421HWB3Z
Created by admin on Fri Dec 15 15:14:31 UTC 2023 , Edited by admin on Fri Dec 15 15:14:31 UTC 2023
PRIMARY
Related Record Type Details
Structure of OXYPHENONIUM
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of OXYPHENONIUM
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