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
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
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
149.0 µM [IC50] | |||
Target ID: CHEMBL2073674 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21965623 |
99.1 µM [IC50] |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/2069584/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/2069584/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/2069584/ |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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
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admin
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Edited
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Record UNII |
K274V650EH
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Record Status |
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Record Version |
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |