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Details

Stereochemistry RACEMIC
Molecular Formula C16H11ClNO3.H4N
Molecular Weight 318.755
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENOXAPROFEN AMMONIUM

SMILES

[NH4+].CC(C([O-])=O)C1=CC2=C(OC(=N2)C3=CC=C(Cl)C=C3)C=C1

InChI

InChIKey=DNGLOBZMXKFACM-UHFFFAOYSA-N
InChI=1S/C16H12ClNO3.H3N/c1-9(16(19)20)11-4-7-14-13(8-11)18-15(21-14)10-2-5-12(17)6-3-10;/h2-9H,1H3,(H,19,20);1H3

HIDE SMILES / InChI
Molecular Formula C16H12ClNO3
Molecular Weight 301.724
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )
Molecular Formula H3N
Molecular Weight 17.0305
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

BENOXAPROFEN is an anti-inflammatory drug indicated for the treatment of arthritis. It was marketed under the brand name ORAFLEX® in the US and as OPREN® in Europe by Eli Lilly and Company. In 1982 Eli Lilly voluntarily withdrew BENOXAPROFEN from the market due to postmarketing reports of severe liver toxicity in patients who took it.

Originator

Approval Year

1982
100
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 149.0 µM [IC50]
Inhibitor
8297
 99.1 µM [IC50]
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
43 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/303114
100 mg 2 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BENOXAPROFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
94 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/6930484
300 mg 2 times / day steady-state, rectal
dose: 300 mg
route of administration: Rectal
experiment type: STEADY-STATE
co-administered:
BENOXAPROFEN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
503 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/303114
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENOXAPROFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.84 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/303114
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENOXAPROFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
38 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/6930484
300 mg 2 times / day steady-state, rectal
dose: 300 mg
route of administration: Rectal
experiment type: STEADY-STATE
co-administered:
BENOXAPROFEN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
600 mg 1 times / day steady, oral
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/6407402/
unhealthy, 35 years (rage: 26-43 years)
n = 20
Health Status: unhealthy
Condition: arthritis
Age Group: 35 years (rage: 26-43 years)
Sex: M+F
Population Size: 20
Sources:
https://pubmed.ncbi.nlm.nih.gov/6407402/
Disc. AE: Photosensitivity...
AEs leading to
discontinuation/dose reduction:
Photosensitivity (11 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/6407402/
900 mg 1 times / day steady, oral
Highest studied dose
Dose: 900 mg, 1 times / day
Route: oral
Route: steady
Dose: 900 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/6803978
unhealthy, 54,9 years (range: 18-86 years)
n = 5
Health Status: unhealthy
Age Group: 54,9 years (range: 18-86 years)
Sex: M+F
Population Size: 5
Sources:
https://pubmed.ncbi.nlm.nih.gov/6803978
Sources:
https://pubmed.ncbi.nlm.nih.gov/6803978
AEs

AEs

AESignificanceDosePopulation
Photosensitivity 11 patient
Disc. AE
600 mg 1 times / day steady, oral
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/6407402/
unhealthy, 35 years (rage: 26-43 years)
n = 20
Health Status: unhealthy
Condition: arthritis
Age Group: 35 years (rage: 26-43 years)
Sex: M+F
Population Size: 20
Sources:
https://pubmed.ncbi.nlm.nih.gov/6407402/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A1
108

CYP1A2
701

CYP4A1
17
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A1
218
 yes
CYP1A2
1692
 yes
CYP4A1
25
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:76114
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:76114
eMolecules
35875742
https://www.emolecules.com/cgi-bin/more?vid=35875742
PubMed

PubMed

TitleDatePubMed
The preferential inhibition of 5-lipoxygenase product formation by benoxaprofen.
1983 Jan
Benoxaprofen photosensitization of phospholipase activation in mammalian cells in culture.
1986 Sep
In vitro inhibition of leukotriene B4 formation by exogeneous 5-lipoxygenase inhibitors is associated with enhanced generation of 15-hydroxy-eicosatetraenoic acid (15-HETE) by human neutrophils.
1988
Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs.
1993 Jan
A systematic review of NSAIDs withdrawn from the market due to hepatotoxicity: lessons learned from the bromfenac experience.
2006 Apr
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.
2014 Jan
Patents

Patents

JP2011524416A
138
JP4267922B2
5
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:24:30 UTC 2023
Edited
by admin
on Sat Dec 16 10:24:30 UTC 2023
Record UNII
825YBQ31XF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENOXAPROFEN AMMONIUM
Common Name English
5-BENZOXAZOLEACETIC ACID, 2-(4-CHLOROPHENYL)-.ALPHA.-METHYL-, AMMONIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
274-298-8
Created by admin on Sat Dec 16 10:24:30 UTC 2023 , Edited by admin on Sat Dec 16 10:24:30 UTC 2023
PRIMARY
PUBCHEM
3017983
Created by admin on Sat Dec 16 10:24:30 UTC 2023 , Edited by admin on Sat Dec 16 10:24:30 UTC 2023
PRIMARY
EPA CompTox
DTXSID30990304
Created by admin on Sat Dec 16 10:24:30 UTC 2023 , Edited by admin on Sat Dec 16 10:24:30 UTC 2023
PRIMARY
FDA UNII
825YBQ31XF
Created by admin on Sat Dec 16 10:24:30 UTC 2023 , Edited by admin on Sat Dec 16 10:24:30 UTC 2023
PRIMARY
CAS
70062-36-1
Created by admin on Sat Dec 16 10:24:30 UTC 2023 , Edited by admin on Sat Dec 16 10:24:30 UTC 2023
PRIMARY
Related Record Type Details
Structure of BENOXAPROFEN AMMONIUM, (S)-
ENANTIOMER -> RACEMATE
Structure of BENOXAPROFEN AMMONIUM, (R)-
ENANTIOMER -> RACEMATE
Structure of BENOXAPROFEN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of BENOXAPROFEN
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