U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of OXAPROZIN POTASSIUM

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 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

Description
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.

Originator

Curator's Comment: Oxaprozin was developed and patented by Wyeth-Ayerst. # Wyeth-Ayerst

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
36.0 µM [IC50]
2.2 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

7.2023042E11
Primary
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

7.2023042E11
Primary
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

7.2023042E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
129 mg/L
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
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
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
2240 mg × h/L
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
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
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
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
54.9 h
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
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
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
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
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
0.21%
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%
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%
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%
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%
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

Doses

DosePopulationAdverse events​
1200 mg single, oral
Highest studied dose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 0.87 uM]
yes [IC50 0.891 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Oxaprozin-induced symptomatic hepatotoxicity.
1999 Sep
A randomized, controlled, single-blind trial of leflunomide in the treatment of rheumatoid arthritis.
2001
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
The "high solubility" definition of the current FDA Guidance on Biopharmaceutical Classification System may be too strict for acidic drugs.
2004 Feb
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
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
Free drug metabolic clearance in elderly people.
2008
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.
2010 Apr 7
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
CK1epsilon is required for breast cancers dependent on beta-catenin activity.
2010 Feb 1
Post-injection delirium/sedation syndrome in patients with schizophrenia treated with olanzapine long-acting injection, I: analysis of cases.
2010 Jun 10
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

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 Jul 05 23:23:26 UTC 2023
Edited
by admin
on Wed Jul 05 23:23:26 UTC 2023
Record UNII
ML56O2Z92I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXAPROZIN POTASSIUM
MART.   ORANGE BOOK   WHO-DD  
Common Name English
Oxaprozin potassium [WHO-DD]
Common Name English
OXAPROZIN POTASSIUM [MART.]
Common Name English
DAYPRO ALTA
Brand Name English
OXAPROZIN POTASSIUM [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1323
Created by admin on Wed Jul 05 23:23:26 UTC 2023 , Edited by admin on Wed Jul 05 23:23:26 UTC 2023
Code System Code Type Description
DRUG BANK
DBSALT001452
Created by admin on Wed Jul 05 23:23:26 UTC 2023 , Edited by admin on Wed Jul 05 23:23:26 UTC 2023
PRIMARY
EPA CompTox
DTXSID70169754
Created by admin on Wed Jul 05 23:23:26 UTC 2023 , Edited by admin on Wed Jul 05 23:23:26 UTC 2023
PRIMARY
FDA UNII
ML56O2Z92I
Created by admin on Wed Jul 05 23:23:26 UTC 2023 , Edited by admin on Wed Jul 05 23:23:26 UTC 2023
PRIMARY
ChEMBL
CHEMBL1071
Created by admin on Wed Jul 05 23:23:26 UTC 2023 , Edited by admin on Wed Jul 05 23:23:26 UTC 2023
PRIMARY
NCI_THESAURUS
C48008
Created by admin on Wed Jul 05 23:23:26 UTC 2023 , Edited by admin on Wed Jul 05 23:23:26 UTC 2023
PRIMARY
CAS
174064-08-5
Created by admin on Wed Jul 05 23:23:26 UTC 2023 , Edited by admin on Wed Jul 05 23:23:26 UTC 2023
PRIMARY
EVMPD
SUB33248
Created by admin on Wed Jul 05 23:23:26 UTC 2023 , Edited by admin on Wed Jul 05 23:23:26 UTC 2023
PRIMARY
SMS_ID
100000125917
Created by admin on Wed Jul 05 23:23:26 UTC 2023 , Edited by admin on Wed Jul 05 23:23:26 UTC 2023
PRIMARY
PUBCHEM
23694685
Created by admin on Wed Jul 05 23:23:26 UTC 2023 , Edited by admin on Wed Jul 05 23:23:26 UTC 2023
PRIMARY
RXCUI
660767
Created by admin on Wed Jul 05 23:23:26 UTC 2023 , Edited by admin on Wed Jul 05 23:23:26 UTC 2023
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY