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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
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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ANTRENYL

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Palliative
ANTRENYL

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5 ng/mL
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
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
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
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
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
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
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
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:
unhealthy, 15-29 years
n = 8
Health Status: unhealthy
Age Group: 15-29 years
Sex: M+F
Population Size: 8
Sources:
Other AEs: Dry mouth...
Other AEs:
Dry mouth (3 patients)
Sources:
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:
unhealthy, 15-29 years
n = 8
Health Status: unhealthy
Age Group: 15-29 years
Sex: M+F
Population Size: 8
Sources:
PubMed

PubMed

TitleDatePubMed
[Software development for calculation of molecular surface area and its application to hydrophobic interaction].
2001 Jan
Cyclodextrins in delivery systems: Applications.
2010 Apr
Patents

Patents

Sample Use Guides

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 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
WHO-ATC A03AB53
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
WHO-VATC QA03AB03
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
WHO-ATC A03AB03
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
Code System Code Type Description
DRUG CENTRAL
2039
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY
NCI_THESAURUS
C78076
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY
IUPHAR
7257
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY
MESH
D010115
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY
EVMPD
SUB14736MIG
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY
FDA UNII
D2G5508Y7I
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY
DRUG BANK
DB00219
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY
PUBCHEM
5749
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY
EPA CompTox
DTXSID8048571
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY
SMS_ID
100000079711
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY
WIKIPEDIA
Oxyphenonium
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY
CAS
14214-84-7
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY
RXCUI
7818
Created by admin on Fri Dec 15 16:11:57 GMT 2023 , Edited by admin on Fri Dec 15 16:11:57 GMT 2023
PRIMARY RxNorm