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

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 of OXAPROZIN

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
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

1992
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

1992
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

1992
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 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
Oxaprozin-induced symptomatic hepatotoxicity.
1999 Sep
The risk of Stevens-Johnson syndrome and toxic epidermal necrolysis associated with nonsteroidal antiinflammatory drugs: a multinational perspective.
2003 Oct
Oxaprozin versus diclofenac in NSAID-refractory periarthritis pain of the shoulder.
2004 Aug
In vitro scavenging activity for reactive oxygen and nitrogen species by nonsteroidal anti-inflammatory indole, pyrrole, and oxazole derivative drugs.
2004 Dec 1
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Subjective impact of osteoarthritis flare-ups on patients' quality of life.
2005 Mar 16
The impact of NSAID or COX-2 inhibitor use on the initiation of antihypertensive therapy.
2006 Dec
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
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
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
p38 MAPK and JNK antagonistically control senescence and cytoplasmic p16INK4A expression in doxorubicin-treated endothelial progenitor cells.
2010 Dec 20
CK1epsilon is required for breast cancers dependent on beta-catenin activity.
2010 Feb 1
Sumatriptan-naproxen fixed combination for acute treatment of migraine: a critical appraisal.
2010 Feb 18
Testing for mean and correlation changes in microarray experiments: an application for pathway analysis.
2010 Jan 28
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
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 Sat Dec 16 16:43:44 GMT 2023
Edited
by admin
on Sat Dec 16 16:43:44 GMT 2023
Record UNII
MHJ80W9LRB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXAPROZIN
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official 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
COXANTO
Brand Name 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
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
NDF-RT N0000000160
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
WHO-VATC QM01AE12
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
NDF-RT N0000175722
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
LIVERTOX NBK548334
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
NCI_THESAURUS C1323
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
NDF-RT N0000175721
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
Code System Code Type Description
DRUG CENTRAL
2013
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
WIKIPEDIA
Oxaprozin
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
DRUG BANK
DB00991
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
IUPHAR
7252
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID1045118
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
MESH
C008729
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL1071
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
EVMPD
SUB09502MIG
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
PUBCHEM
4614
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
CAS
21256-18-8
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
244-296-1
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
NCI_THESAURUS
C29307
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
HSDB
7586
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
MERCK INDEX
m8293
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY Merck Index
FDA UNII
MHJ80W9LRB
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
NSC
310839
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
RS_ITEM_NUM
1482207
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
RXCUI
32613
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY RxNorm
DAILYMED
MHJ80W9LRB
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PRIMARY
INN
3458
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
SMS_ID
100000092177
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
CHEBI
7822
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
LACTMED
Oxaprozin
Created by admin on Sat Dec 16 16:43:45 GMT 2023 , Edited by admin on Sat Dec 16 16:43:45 GMT 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
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METABOLITE -> PARENT
BILE
METABOLITE -> PARENT
METABOLITE -> PARENT
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CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC