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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
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ANTRENYL
Primary
Unknown
Palliative
ANTRENYL

Cmax

ValueDoseCo-administeredAnalytePopulation
80 ng/mL
2 mg single, intramuscular
OXYPHENONIUM plasma
Homo sapiens
5 ng/mL
10 mg single, oral
OXYPHENONIUM plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
5.9 μg × min/mL
2 mg single, intravenous
OXYPHENONIUM plasma
Homo sapiens
4.6 μg × min/mL
2 mg single, intramuscular
OXYPHENONIUM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
2 mg single, intravenous
OXYPHENONIUM plasma
Homo sapiens
130 min
2 mg single, intramuscular
OXYPHENONIUM plasma
Homo sapiens
190 min
10 mg single, oral
OXYPHENONIUM plasma
Homo sapiens

Doses

AEs

Sourcing

PubMed

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
Record UNII
S9421HWB3Z
Record Status Validated (UNII)
Record Version