OXAPROZIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H15NO3
Molecular Weight	293.3166
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CCC1=NC(=C(O1)C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=OFPXSFXSNFPTHF-UHFFFAOYSA-N

InChI=1S/C18H15NO3/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)

HIDE SMILES / InChI

Molecular Formula	C18H15NO3
Molecular Weight	293.3166
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9650852	Inhibitor 8504		36.0 µM [IC50]
Cyclooxygenase-1 131 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9650852	Inhibitor 8504		2.2 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis 157 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018841s028lbl.pdf	Primary	Approved 8583	DAYPRO Approved Use DAYPRO 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 Date 1992
Rheumatoid arthritis 320 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018841s028lbl.pdf	Primary	Approved 8583	DAYPRO Approved Use DAYPRO 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 Date 1992
Juvenile rheumatoid arthritis 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018841s028lbl.pdf	Primary	Approved 8583	DAYPRO Approved Use DAYPRO 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 Date 1992

C_max

Value	Dose	Analyte	Population
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
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
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

AUC

Value	Dose	Analyte	Population
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
1290 mg × h/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
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

T_1/2

Value	Dose	Analyte	Population
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
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
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

F_unbound

Value	Dose	Analyte	Population
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
0.208% 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
0.305% 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
0.457% 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
0.823% 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

Doses

Dose	Population	Adverse events
1200 mg single, oral Highest studied dose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1617910/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/1617910/	Sources: https://pubmed.ncbi.nlm.nih.gov/1617910/
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: https://pubmed.ncbi.nlm.nih.gov/9884815/	healthy, adult Health Status: healthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/9884815/	Sources: https://pubmed.ncbi.nlm.nih.gov/9884815/
20 mg/kg single, oral Highest studied dose Dose: 20 mg/kg Route: oral Route: single Dose: 20 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/1617910/	unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/1617910/	Sources: https://pubmed.ncbi.nlm.nih.gov/1617910/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 725 OAT3 747	CYP 303 UGT 219

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22973893/	yes [IC50 0.87 uM]
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22973893/	yes [IC50 0.891 uM]

Drug as victim

Target	Modality	Activity
CYP 303	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/7357792/	yes
CYP2C9 1193	substrate 4014 Sources: https://www.longdom.org/open-access/drug-interactions-involving-the-cytochrome-p450-enzymes-analysis-of-common-combinations-of-antibiotics-and-pain-relieving-drugs-2157-7609.1000131.pdf	yes
UGT 219	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/7357792/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7822	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7822
ChemicalBook	CB1272505	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1272505
eMolecules	593100	https://www.emolecules.com/cgi-bin/more?vid=593100
MolPort	MolPort-000-146-829	https://www.molport.com/shop/molecule-link/MolPort-000-146-829
ZINC	ZINC000049643479	http://zinc15.docking.org/substances/ZINC000049643479

PubMed

Title	Date	PubMed
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015-05-18	25811541
p38 MAPK and JNK antagonistically control senescence and cytoplasmic p16INK4A expression in doxorubicin-treated endothelial progenitor cells.	2010-12-20	21187925
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Magnetic Fe₃O₄ nanoparticles and chemotherapy agents interact synergistically to induce apoptosis in lymphoma cells.	2010-11-19	21187919
Effect of ketorolac and diclofenac on the impairment of endothelium-dependent relaxation induced by reactive oxygen species in rabbit abdominal aorta.	2010-09	20877705
Post-injection delirium/sedation syndrome in patients with schizophrenia treated with olanzapine long-acting injection, I: analysis of cases.	2010-06-10	20537128
Analgesic and anti-inflammatory effects of oxaprozin and naproxen sodium after removal of impacted lower third molars: a randomized, double-blind, placebo-controlled crossover study.	2010-05	20206429
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.	2010-04-07	20396637
Theoretical and vibrational studies of 4,5-diphenyl-2-2 oxazole propionic acid (oxaprozin).	2010-04	20167532
Sumatriptan-naproxen fixed combination for acute treatment of migraine: a critical appraisal.	2010-02-18	20368903
Nonsteroidal Anti-Inflammatory Drugs: A survey of practices and concerns of pediatric medical and surgical specialists and a summary of available safety data.	2010-02-04	20181090
CK1epsilon is required for breast cancers dependent on beta-catenin activity.	2010-02-01	20126544
Testing for mean and correlation changes in microarray experiments: an application for pathway analysis.	2010-01-28	20109181
Development of a new delivery system consisting in 'drug-in cyclodextrin-in PLGA nanoparticles'.	2010	20113170
Design, synthesis, and in-vivo evaluation of 4,5-diaryloxazole as novel nonsteroidal anti-inflammatory drug.	2009-12	19952416
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009-10-02	19798416
Delayed apoptosis of human monocytes exposed to immune complexes is reversed by oxaprozin: role of the Akt/IkappaB kinase/nuclear factor kappaB pathway.	2009-05	19338579
Oxaprozin-induced apoptosis on CD40 ligand-treated human primary monocytes is associated with the modulation of defined intracellular pathways.	2009	19672323
Development of a selective molecularly imprinted polymer-based solid-phase extraction for indomethacin from water samples.	2008-08	18575852
Topical ocular delivery of NSAIDs.	2008-06	18437583
Spread pattern of the first dengue epidemic in the city of Salvador, Brazil.	2008-02-07	18257919
Singlet oxygen scavenging activity of non-steroidal anti-inflammatory drugs.	2008	18647485
Free drug metabolic clearance in elderly people.	2008	18399712
A peripatetic pediatrician's journey into pediatric rheumatology: Part II.	2007-06-21	17584931
The aryl propionic acid R-flurbiprofen selectively induces p75NTR-dependent decreased survival of prostate tumor cells.	2007-04-01	17409433
In silico prediction of pregnane X receptor activators by machine learning approaches.	2007-01	17003167
Early onset pauciarticular arthritis is the major risk factor for naproxen-induced pseudoporphyria in juvenile idiopathic arthritis.	2007	17266758
The impact of NSAID or COX-2 inhibitor use on the initiation of antihypertensive therapy.	2006-12	17024689
Studies on the interaction between Oxaprozin-E and bovine serum albumin by spectroscopic methods.	2006-11-15	16828154
Effects of isopropyl palmitate on the skin permeation of drugs.	2006-11	17077540
An exploratory theoretical elucidation on the peroxyl-radical-scavenging mechanism and structure-activity relationship of nonsteroidal anti-inflammatory drugs.	2006-06-15	16600595
Effects of Transcutol P on the corneal permeability of drugs and evaluation of its ocular irritation of rabbit eyes.	2006-01	16393463
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Analytic performance evaluation of a new turbidimetric immunoassay for phenytoin on the ADVIA 1650 analyzer: effect of phenytoin metabolite and analogue.	2005-06	15905800
A review of the emerging profile of the anti-inflammatory drug oxaprozin.	2005-05	15934904
Hydrogen peroxide scavenging activity by non-steroidal anti-inflammatory drugs.	2005-04-29	15808884
Patient characteristics associated with outpatient prescriptions for nabumetone and oxaprozin versus celecoxib and rofecoxib.	2005-04-01	15790802
Subjective impact of osteoarthritis flare-ups on patients' quality of life.	2005-03-16	15771777
In vitro scavenging activity for reactive oxygen and nitrogen species by nonsteroidal anti-inflammatory indole, pyrrole, and oxazole derivative drugs.	2004-12-01	15528048
Oxaprozin versus diclofenac in NSAID-refractory periarthritis pain of the shoulder.	2004-08	15324531
Oxaprozin: kinetic and dynamic profile in the treatment of pain.	2004-08	15324530
The "high solubility" definition of the current FDA Guidance on Biopharmaceutical Classification System may be too strict for acidic drugs.	2004-02	15032311
Spontaneous reports of hypertension leading to hospitalisation in association with rofecoxib, celecoxib, nabumetone and oxaprozin.	2004	15132714
[Meta-analysis on the effect and adverse reaction on patients with osteoarthritis and rheumatoid arthritis treated with non-steroidal anti-inflammatory drugs].	2003-11	14687510
The risk of Stevens-Johnson syndrome and toxic epidermal necrolysis associated with nonsteroidal antiinflammatory drugs: a multinational perspective.	2003-10	14528522
Search of antimicrobial activity of selected non-antibiotic drugs.	2003-04-03	12669766
Nonsteroidal antiinflammatory drug-induced pseudoporphyria: a case series.	2002-07-16	12118363
Nonsteroidal anti-inflammatory drugs induce apoptosis in association with activation of peroxisome proliferator-activated receptor gamma in rheumatoid synovial cells.	2002-07	12065695
Comparison of cyclooxygenase-1 and -2 inhibitory activities of various nonsteroidal anti-inflammatory drugs using human platelets and synovial cells.	1998-04-17	9650852
Oxaprozin-induced fulminant hepatitis.	1994-10	7841569

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Wed Apr 02 08:20:09 GMT 2025` Edited by `admin` on `Wed Apr 02 08:20:09 GMT 2025`
Record UNII	MHJ80W9LRB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXAPROZIN

Official Name

English

COXANTO

Preferred Name

English

OXAPROZIN [MART.]

Common Name

English

4,5-DIPHENYL-2-OXAZOLEPROPANOIC ACID

Systematic Name

English

OXAPROZIN [USP MONOGRAPH]

Common Name

English

OXAPROZIN [JAN]

Common Name

English

NSC-310839

Code

English

OXAPROZIN [USP-RS]

Common Name

English

DAYPRO

Brand Name

English

OXAPROZIN [HSDB]

Common Name

English

OXAPROZIN [MI]

Common Name

English

OXAPROZIN [VANDF]

Common Name

English

OXAPROZIN [ORANGE BOOK]

Common Name

English

WY-21743

Code

English

2-OXAZOLEPROPANOIC ACID, 4,5-DIPHENYL-

Common Name

English

WY-21,743

Code

English

Oxaprozin [WHO-DD]

Common Name

English

OXAPROZIN [USAN]

Common Name

English

oxaprozin [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

M01AE12