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Details

Stereochemistry RACEMIC
Molecular Formula C16H12ClNO3
Molecular Weight 301.724
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENOXAPROFEN

SMILES

CC(C(O)=O)C1=CC2=C(OC(=N2)C3=CC=C(Cl)C=C3)C=C1

InChI

InChIKey=MITFXPHMIHQXPI-UHFFFAOYSA-N
InChI=1S/C16H12ClNO3/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)

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 ( + / - )

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
Nonsteroid anti-inflammatory agents: regulators of the phagocytic secretion of lysosomal enzymes from guinea-pig neutrophils.
1978 Nov
Long-term safety of benoxaprofen.
1980
An update on long-term efficacy and safety with benoxaprofen.
1982
Effects of benoxaprofen on human neutrophil function.
1984 Jun
Benoxaprofen photosensitization of cell membrane disruption.
1984 Mar
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 Fri Dec 15 15:19:11 GMT 2023
Edited
by admin
on Fri Dec 15 15:19:11 GMT 2023
Record UNII
17SZX404IM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENOXAPROFEN
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
COMPD 90459
Code English
benoxaprofen [INN]
Common Name English
BENOXAPROFEN [MART.]
Common Name English
OPREN
Brand Name English
COMPOUND-90459
Code English
BENOXAPROFEN [JAN]
Common Name English
5-BENZOXAZOLEACETIC ACID, 2-(4-CHLOROPHENYL)-.ALPHA.-METHYL, (±)-
Common Name English
Benoxaprofen [WHO-DD]
Common Name English
BENOXAPROFEN [USAN]
Common Name English
COMPOUND 90459
Code English
BENOXAPROFEN [MI]
Common Name English
NSC-299582
Code English
(±)-2-(P-CHLOROPHENYL)-.ALPHA.-METHYL-5-BENZOXAZOLEACETIC ACID
Common Name English
COXIGON
Brand Name English
ORAFLEX
Brand Name English
Classification Tree Code System Code
WHO-VATC QM01AE06
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
NCI_THESAURUS C257
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
WHO-ATC M01AE06
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
257-069-7
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
DRUG BANK
DB04812
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
MERCK INDEX
m578
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL340978
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
NSC
299582
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
SMS_ID
100000086354
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
INN
3896
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID4022650
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
EVMPD
SUB05725MIG
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
NCI_THESAURUS
C76796
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
WIKIPEDIA
BENOXAPROFEN
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
DRUG CENTRAL
311
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
PUBCHEM
39941
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
CHEBI
76114
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
FDA UNII
17SZX404IM
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
CAS
67434-14-4
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
SUPERSEDED
CAS
51234-28-7
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
MESH
C011677
Created by admin on Fri Dec 15 15:19:11 GMT 2023 , Edited by admin on Fri Dec 15 15:19:11 GMT 2023
PRIMARY
Related Record Type Details
Structure of BENOXAPROFEN, (R)-
ENANTIOMER -> RACEMATE
Structure of BENOXAPROFEN, (S)-
ENANTIOMER -> RACEMATE
Structure of BENOXAPROFEN AMMONIUM
SALT/SOLVATE -> PARENT
Structure of BENOXAPROFEN SODIUM
SALT/SOLVATE -> PARENT
Structure of BENOXAPROFEN POTASSIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of BENOXAPROFEN
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