Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H14NO3.K |
Molecular Weight | 331.407 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[K+].[O-]C(=O)CCC1=NC(=C(O1)C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=QTAQWNSMRSLSCG-UHFFFAOYSA-M
InChI=1S/C18H15NO3.K/c20-16(21)12-11-15-19-17(13-7-3-1-4-8-13)18(22-15)14-9-5-2-6-10-14;/h1-10H,11-12H2,(H,20,21);/q;+1/p-1
Molecular Formula | C18H14NO3 |
Molecular Weight | 292.3087 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | K |
Molecular Weight | 39.0983 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00991Curator's Comment: Description was created based on several sources, including https://www.oolac.com/dictionary/en/en/tag/Oxazoles and https://www.ncbi.nlm.nih.gov/pubmed/15934904
Sources: http://www.drugbank.ca/drugs/DB00991
Curator's Comment: Description was created based on several sources, including https://www.oolac.com/dictionary/en/en/tag/Oxazoles and https://www.ncbi.nlm.nih.gov/pubmed/15934904
Oxaprozin is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Anti-inflammatory effects of Oxaprozin are believed to be due to inhibition of cylooxygenase in platelets which leads to the blockage of prostaglandin synthesis. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Oxaprozin is a non-selective NSAID, with a cell assay system showing lower COX-2 selectivity implying higher COX-1 selectivity. Oxaprozin is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and to alleviate moderate pain.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9650852 |
36.0 µM [IC50] | ||
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9650852 |
2.2 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DAYPRO Approved UseDAYPRO is a non-steroidal anti-inflammatory drug indicated for:
Relief of signs and symptoms of Osteoarthritis (OA)
Relief of signs and symptoms of Rheumatoid Arthritis (RA)
Relief of signs and symptoms of Juvenile Rheumatoid Arthritis Launch Date1992 |
|||
Primary | DAYPRO Approved UseDAYPRO is a non-steroidal anti-inflammatory drug indicated for:
Relief of signs and symptoms of Osteoarthritis (OA)
Relief of signs and symptoms of Rheumatoid Arthritis (RA)
Relief of signs and symptoms of Juvenile Rheumatoid Arthritis Launch Date1992 |
|||
Primary | DAYPRO Approved UseDAYPRO is a non-steroidal anti-inflammatory drug indicated for:
Relief of signs and symptoms of Osteoarthritis (OA)
Relief of signs and symptoms of Rheumatoid Arthritis (RA)
Relief of signs and symptoms of Juvenile Rheumatoid Arthritis Launch Date1992 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
129 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
174 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.8 g single, oral dose: 1.8 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
239 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.2 g 1 times / day steady-state, oral dose: 1.2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
280 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.8 g 1 times / day steady-state, oral dose: 1.8 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
78.4 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
0.6 g single, oral dose: 0.6 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
103 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6480879/ |
1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
109 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6480879/ |
1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2240 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2970 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.8 g single, oral dose: 1.8 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4210 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.2 g 1 times / day steady-state, oral dose: 1.2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4770 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.8 g 1 times / day steady-state, oral dose: 1.8 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1290 mg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
0.6 g single, oral dose: 0.6 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
7042 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6480879/ |
1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7066 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6480879/ |
1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
54.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
47 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.8 g single, oral dose: 1.8 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
41.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.2 g 1 times / day steady-state, oral dose: 1.2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
58.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
0.6 g single, oral dose: 0.6 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
50 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6480879/ |
1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
48 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6480879/ |
1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.21% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.2 g single, oral dose: 1.2 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.8 g single, oral dose: 1.8 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.46% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.2 g 1 times / day steady-state, oral dose: 1.2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.82% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
1.8 g 1 times / day steady-state, oral dose: 1.8 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.13% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8973987/ |
0.6 g single, oral dose: 0.6 g route of administration: Oral experiment type: SINGLE co-administered: |
OXAPROZIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
1200 mg single, oral Highest studied dose |
unhealthy, adult Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Sex: unknown Sources: |
|
1200 mg 1 times / day steady, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: steady Dose: 1200 mg, 1 times / day Sources: |
healthy, adult n = 10 Health Status: healthy Age Group: adult Sex: unknown Population Size: 10 Sources: |
|
20 mg/kg single, oral Highest studied dose Dose: 20 mg/kg Route: oral Route: single Dose: 20 mg/kg Sources: |
unhealthy, children Health Status: unhealthy Condition: rheumatoid arthritis Age Group: children Sex: unknown Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Oxaprozin-induced fulminant hepatitis. | 1994 Oct |
|
Comparison of cyclooxygenase-1 and -2 inhibitory activities of various nonsteroidal anti-inflammatory drugs using human platelets and synovial cells. | 1998 Apr 17 |
|
Pharmacological profile of oxaprozin eye drops. | 2002 Feb |
|
Nonsteroidal antiinflammatory drug-induced pseudoporphyria: a case series. | 2002 Jul-Aug |
|
The risk of Stevens-Johnson syndrome and toxic epidermal necrolysis associated with nonsteroidal antiinflammatory drugs: a multinational perspective. | 2003 Oct |
|
In vitro scavenging activity for reactive oxygen and nitrogen species by nonsteroidal anti-inflammatory indole, pyrrole, and oxazole derivative drugs. | 2004 Dec 1 |
|
Patient characteristics associated with outpatient prescriptions for nabumetone and oxaprozin versus celecoxib and rofecoxib. | 2005 Apr 1 |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Studies on the interaction between Oxaprozin-E and bovine serum albumin by spectroscopic methods. | 2006 Nov 15 |
|
In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
|
Singlet oxygen scavenging activity of non-steroidal anti-inflammatory drugs. | 2008 |
|
Development of a selective molecularly imprinted polymer-based solid-phase extraction for indomethacin from water samples. | 2008 Aug |
|
Design, synthesis, and in-vivo evaluation of 4,5-diaryloxazole as novel nonsteroidal anti-inflammatory drug. | 2009 Dec |
|
Delayed apoptosis of human monocytes exposed to immune complexes is reversed by oxaprozin: role of the Akt/IkappaB kinase/nuclear factor kappaB pathway. | 2009 May |
|
Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
|
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
Sumatriptan-naproxen fixed combination for acute treatment of migraine: a critical appraisal. | 2010 Feb 18 |
|
Magnetic Fe₃O₄ nanoparticles and chemotherapy agents interact synergistically to induce apoptosis in lymphoma cells. | 2010 Nov 19 |
|
Effect of ketorolac and diclofenac on the impairment of endothelium-dependent relaxation induced by reactive oxygen species in rabbit abdominal aorta. | 2010 Sep |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/oxaprozin.html
Usual Adult Dose for Osteoarthritis
Loading dose: 1200 mg to 1800 mg orally; not to exceed 26 mg/kg
Maintenance dose: 1200 mg orally once a day
Maximum dose: 1800 mg or 26 mg/kg orally per day, whichever is less, in divided doses
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6432657
In arachidonic acid (AA)-induced rabbit platelet aggregation in vitro, oxaprozin exhibited a dose-dependent inhibitory effect with MIC 124.2 uM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:55:04 GMT 2023
by
admin
on
Fri Dec 15 15:55:04 GMT 2023
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Record UNII |
ML56O2Z92I
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C1323
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DBSALT001452
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DTXSID70169754
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ML56O2Z92I
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CHEMBL1071
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C48008
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174064-08-5
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660767
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |