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
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
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
| 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: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Nonsteroid anti-inflammatory agents: regulators of the phagocytic secretion of lysosomal enzymes from guinea-pig neutrophils. | 1978 Nov |
|
| The preferential inhibition of 5-lipoxygenase product formation by benoxaprofen. | 1983 Jan |
|
| Benoxaprofen improves psoriasis. A double-blind study. | 1983 Jul |
|
| Effects of benoxaprofen on human neutrophil function. | 1984 Jun |
|
| Benoxaprofen photosensitization of cell membrane disruption. | 1984 Mar |
|
| Interaction of benoxaprofen with rat erythrocytes: effects on oxidative metabolism and membrane ATPase activities. | 1986 Nov |
|
| 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 |
|
| Species difference of 5-lipoxygenase derived from polymorphonuclear leukocytes on sensitivity to drugs. | 1989 May |
|
| Induction of the cytochrome P450 I and IV families and peroxisomal proliferation in the liver of rats treated with benoxaprofen. Possible implications in its hepatotoxicity. | 1991 Jun 21 |
|
| A systematic review of NSAIDs withdrawn from the market due to hepatotoxicity: lessons learned from the bromfenac experience. | 2006 Apr |
|
| Glucuronidation and covalent protein binding of benoxaprofen and flunoxaprofen in sandwich-cultured rat and human hepatocytes. | 2009 Dec |
|
| 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
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274-298-8
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3017983
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DTXSID30990304
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825YBQ31XF
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70062-36-1
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ACTIVE MOIETY
SUBSTANCE RECORD
