OXAPROZIN POTASSIUM

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

Structure Search

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

HIDE SMILES / InChI

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

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

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
Nonsteroidal anti-inflammatory drugs induce apoptosis in association with activation of peroxisome proliferator-activated receptor gamma in rheumatoid synovial cells.	2002 Jul	12065695
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
In silico prediction of pregnane X receptor activators by machine learning approaches.	2007 Jan	17003167
Singlet oxygen scavenging activity of non-steroidal anti-inflammatory drugs.	2008	18647485
Free drug metabolic clearance in elderly people.	2008	18399712
Development of a selective molecularly imprinted polymer-based solid-phase extraction for indomethacin from water samples.	2008 Aug	18575852
Topical ocular delivery of NSAIDs.	2008 Jun	18437583
Development of a new delivery system consisting in 'drug-in cyclodextrin-in PLGA nanoparticles'.	2010	20113170
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.	2010 Apr 7	20396637
CK1epsilon is required for breast cancers dependent on beta-catenin activity.	2010 Feb 1	20126544
Sumatriptan-naproxen fixed combination for acute treatment of migraine: a critical appraisal.	2010 Feb 18	20368903
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 May	20206429
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

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 `Mon Mar 31 18:13:09 GMT 2025` Edited by `admin` on `Mon Mar 31 18:13:09 GMT 2025`
Record UNII	ML56O2Z92I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXAPROZIN POTASSIUM

Common Name

English

DAYPRO ALTA

Preferred Name

English

Oxaprozin potassium [WHO-DD]

Common Name

English

OXAPROZIN POTASSIUM [MART.]

Common Name

English

OXAPROZIN POTASSIUM [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1323