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Details

Stereochemistry RACEMIC
Molecular Formula C16H11ClNO3.Na
Molecular Weight 323.706
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENOXAPROFEN SODIUM

SMILES

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

InChI

InChIKey=ZJVWYIWJRVXGKT-UHFFFAOYSA-M
InChI=1S/C16H12ClNO3.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H11ClNO3
Molecular Weight 300.716
Charge -1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
43 μg/mL
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
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
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
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
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:
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:
Disc. AE: Photosensitivity...
AEs leading to
discontinuation/dose reduction:
Photosensitivity (11 patient)
Sources:
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:
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:
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:
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

PubMed

PubMed

TitleDatePubMed
Nonsteroid anti-inflammatory agents: regulators of the phagocytic secretion of lysosomal enzymes from guinea-pig neutrophils.
1978 Nov
A comparative study of benoxaprofen and ibuprofen in osteoarthritis in general practice.
1980
Long-term safety of benoxaprofen.
1980
Toxic optic neuropathy caused by benoxaprofen.
1981 Jul 18
An update on long-term efficacy and safety with benoxaprofen.
1982
The preferential inhibition of 5-lipoxygenase product formation by benoxaprofen.
1983 Jan
Benoxaprofen improves psoriasis. A double-blind study.
1983 Jul
The aetiology of psoriasis: clues provided by benoxaprofen.
1983 Jul
[Vasculitis caused by benoxaprofen].
1983 Oct 8
Inhibition of steroid production in Leydig cells by non-steroidal anti-inflammatory and related compounds: evidence for the involvement of lipoxygenase products in steroidogenesis.
1984 Apr 15
Effects of benoxaprofen on human neutrophil function.
1984 Jun
Benoxaprofen photosensitization of cell membrane disruption.
1984 Mar
Effects of some non-steroidal anti-inflammatory drugs and other agents on cyclooxygenase and lipoxygenase activities in some enzyme preparations.
1985 Jun
Meclofenamate sodium is an inhibitor of both the 5-lipoxygenase and cyclooxygenase pathways of the arachidonic acid cascade in vitro.
1986 Aug
Primary biliary cirrhosis after benoxaprofen.
1986 Jul 26
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
Simple procedure for measuring the pharmacodynamics and analgesic potential of lipoxygenase inhibitors.
1988 Dec
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
Carboxylic acid drug-induced DNA nicking in HEK293 cells expressing human UDP-glucuronosyltransferases: role of acyl glucuronide metabolites and glycation pathways.
2007 Oct
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:24:29 GMT 2023
Edited
by admin
on Sat Dec 16 10:24:29 GMT 2023
Record UNII
K274V650EH
Record Status Validated (UNII)
Record Version
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Name Type Language
BENOXAPROFEN SODIUM
Common Name English
5-BENZOXAZOLEACETIC ACID, 2-(4-CHLOROPHENYL)-.ALPHA.-METHYL-, SODIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID80965527
Created by admin on Sat Dec 16 10:24:29 GMT 2023 , Edited by admin on Sat Dec 16 10:24:29 GMT 2023
PRIMARY
PUBCHEM
23684809
Created by admin on Sat Dec 16 10:24:29 GMT 2023 , Edited by admin on Sat Dec 16 10:24:29 GMT 2023
PRIMARY
CAS
51234-86-7
Created by admin on Sat Dec 16 10:24:29 GMT 2023 , Edited by admin on Sat Dec 16 10:24:29 GMT 2023
PRIMARY
ECHA (EC/EINECS)
257-071-8
Created by admin on Sat Dec 16 10:24:29 GMT 2023 , Edited by admin on Sat Dec 16 10:24:29 GMT 2023
PRIMARY
FDA UNII
K274V650EH
Created by admin on Sat Dec 16 10:24:29 GMT 2023 , Edited by admin on Sat Dec 16 10:24:29 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY