Identification

Name
Oxaprozin
Accession Number
DB00991  (APRD00030)
Type
Small Molecule
Groups
Approved
Description

Oxaprozin is a non-narcotic, non-steroidal anti-inflammatory drug (NSAID), used to relieve the inflammation, swelling, stiffness, and joint pain associated with osteoarthritis and rheumatoid arthritis.

Structure
Thumb
Synonyms
  • Danoprox
  • Dayrun
  • Deflam
  • Duraprox
  • Oxaprozina
  • Oxaprozine
  • Oxaprozinum
  • Walix
External IDs
WY-21,743
Product Ingredients
IngredientUNIICASInChI Key
Oxaprozin potassiumML56O2Z92I174064-08-5QTAQWNSMRSLSCG-UHFFFAOYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DayproTablet600 mgOralPfizer1997-01-072012-09-20Canada
DayproTablet, film coated600 mg/1OralPd Rx Pharmaceuticals, Inc.1992-10-29Not applicableUs
DayproTablet, film coated600 mg/1OralG.D. Searle LLC Division of Pfizer Inc1992-10-29Not applicableUs00025 1381 31 nlmimage10 811340aa
DayproTablet, film coated600 mg/1OralPhysicians Total Care, Inc.1992-10-292010-06-30Us
Daypro AltaTablet, film coated600 mg/1OralG.D. Searle LLC Division of Pfizer Inc2002-10-172007-08-10Us
OxaprozinTablet, film coated600 mg/1OralNeolpharma, Inc.1992-10-29Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-oxaprozinTablet600 mgOralApotex Corporation2001-05-29Not applicableCanada
OxaprozinTablet600 mg/1Oralbryant ranch prepack2017-05-04Not applicableUs
OxaprozinTablet, film coated600 mg/1OralUnit Dose Services2003-05-12Not applicableUs00093 0924 01 nlmimage10 b729dbee
OxaprozinTablet, film coated600 mg/1OralH.J. Harkins Company2001-01-31Not applicableUs
OxaprozinTablet600 mg/1OralAv Kare, Inc.2014-03-062018-09-18Us
OxaprozinTablet600 mg/1OralDirectrx2014-01-01Not applicableUs
OxaprozinTablet, film coated600 mg/1Oralbryant ranch prepack2003-05-12Not applicableUs63629 134520180913 8702 uuwm71
OxaprozinTablet, film coated600 mg/1OralA-S Medication Solutions2001-01-31Not applicableUs54569 521220180907 15195 swy58y
OxaprozinTablet600 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2002-01-03Not applicableUs
OxaprozinTablet600 mg/1Oralbryant ranch prepack2001-01-31Not applicableUs
International/Other Brands
Alvo / Daypro / Daypro Alta
Categories
UNII
MHJ80W9LRB
CAS number
21256-18-8
Weight
Average: 293.3166
Monoisotopic: 293.105193351
Chemical Formula
C18H15NO3
InChI Key
OFPXSFXSNFPTHF-UHFFFAOYSA-N
InChI
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)
IUPAC Name
3-(diphenyl-1,3-oxazol-2-yl)propanoic acid
SMILES
OC(=O)CCC1=NC(=C(O1)C1=CC=CC=C1)C1=CC=CC=C1

Pharmacology

Indication

Used to relieve the inflammation, swelling, stiffness, and joint pain associated with rheumatoid arthritis and osteoarthritis.

Associated Conditions
Pharmacodynamics

Oxaprozin is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Oxaprozin is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and to alleviate moderate pain.

Mechanism of action

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.

TargetActionsOrganism
AProstaglandin G/H synthase 1
inhibitor
Human
AProstaglandin G/H synthase 2
inhibitor
Human
Absorption

Oxaprozin is 95% absorbed after oral administration. Food may reduce the rate of absorption of oxaprozin, but the extent of absorption is unchanged. Antacids do not significantly affect the extent and rate of oxaprozin absorption.

Volume of distribution
  • 11 to 17 L/70 kg
Protein binding

>99.5% bound to albumin

Metabolism

Hepatic. Ester and ether glucuronide are the major conjugated metabolites of oxaprozin, and do not have significant pharmacologic activity.

Route of elimination

Oxaprozin is expected to be excreted in human milk based on its physical-chemical properties; however, the amount of oxaprozin excreted in breast milk has not been evaluated. Approximately 95% of oxaprozin is metabolized by the liver. Approximately 5% of the oxaprozin dose is excreted unchanged in the urine. Sixty-five percent (65%) of the dose is excreted in the urine and 35% in the feces as metabolite. Biliary excretion of unchanged oxaprozin is a minor pathway. Several oxaprozin metabolites have been identified in human urine or feces.

Half life

54.9 hours

Clearance
Not Available
Toxicity

Oral, mouse: LD50 = 1210 mg/kg; Oral, rabbit: LD50 = 172 mg/kg; Oral, rat: LD50 = 4470 mg/kg

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Oxaprozin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Oxaprozin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Oxaprozin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of gastrointestinal bleeding can be increased when Oxaprozin is combined with 4-hydroxycoumarin.
AbacavirOxaprozin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Oxaprozin is combined with Abciximab.
AcarboseOxaprozin may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololOxaprozin may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Oxaprozin is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Oxaprozin is combined with Acemetacin.
AcenocoumarolThe risk or severity of gastrointestinal bleeding can be increased when Oxaprozin is combined with Acenocoumarol.
Food Interactions
  • Take with food, usually once a day after breakfast. Food decreases the rate of absorption but not the amount absorbed. Avoid alcohol.

References

Synthesis Reference

Zhou XP, Zhang MX, Sun W, Yang XH, Wang GS, Sui DY, Yu XF, Qu SC: Design, synthesis, and in-vivo evaluation of 4,5-diaryloxazole as novel nonsteroidal anti-inflammatory drug. Biol Pharm Bull. 2009 Dec;32(12):1986-90. Pubmed.

General References
  1. Heller B, Tarricone R: Oxaprozin versus diclofenac in NSAID-refractory periarthritis pain of the shoulder. Curr Med Res Opin. 2004 Aug;20(8):1279-90. [PubMed:15324531]
External Links
Human Metabolome Database
HMDB0015126
KEGG Drug
D00463
KEGG Compound
C07356
PubChem Compound
4614
PubChem Substance
46506429
ChemSpider
4453
BindingDB
50002861
ChEBI
7822
ChEMBL
CHEMBL1071
Therapeutic Targets Database
DAP000622
PharmGKB
PA450730
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Oxaprozin
ATC Codes
M01AE12 — Oxaprozin
AHFS Codes
  • 28:08.04.92 — Other Nonsteroidal Antiimflammatory Agents
FDA label
Download (47 KB)
MSDS
Download (63.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers1

Pharmacoeconomics

Manufacturers
  • Gd searle llc
  • Actavis elizabeth llc
  • Apotex inc etobicoke site
  • Caraco pharmaceutical laboratories ltd
  • Dr reddys laboratories ltd
  • Genpharm inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories
Packagers
  • Aidarex Pharmacuticals LLC
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Blenheim Pharmacal
  • Bryant Ranch Prepack
  • Caraco Pharmaceutical Labs
  • Corepharma LLC
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Eon Labs
  • GD Searle LLC
  • H.J. Harkins Co. Inc.
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PD-Rx Pharmaceuticals Inc.
  • Pharmacia Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prescription Dispensing Service Inc.
  • Rebel Distributors Corp.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
Dosage forms
FormRouteStrength
TabletOral600 mg
TabletOral600 mg/1
Tablet, film coatedOral600 mg/1
Prices
Unit descriptionCostUnit
Daypro 600 mg tablet2.98USD tablet
Daypro 600 mg caplet2.87USD caplet
Oxaprozin 600 mg tablet1.54USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6030643No1997-05-162017-05-16Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)158-159 °CNot Available
water solubilityInsolubleNot Available
logP4.19HANSCH,C ET AL. (1995)
pKa4.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0325 mg/mLALOGPS
logP3.33ALOGPS
logP3.46ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
pKa (Strongest Basic)-0.59ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.33 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity81.88 m3·mol-1ChemAxon
Polarizability31.69 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9512
Caco-2 permeable-0.5255
P-glycoprotein substrateNon-substrate0.7938
P-glycoprotein inhibitor INon-inhibitor0.8801
P-glycoprotein inhibitor IINon-inhibitor0.9047
Renal organic cation transporterNon-inhibitor0.8467
CYP450 2C9 substrateNon-substrate0.7623
CYP450 2D6 substrateNon-substrate0.8163
CYP450 3A4 substrateNon-substrate0.5781
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9327
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.93
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6313
Ames testNon AMES toxic0.9191
CarcinogenicityNon-carcinogens0.9364
BiodegradationReady biodegradable0.6095
Rat acute toxicity1.8484 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9906
hERG inhibition (predictor II)Non-inhibitor0.9123
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0090000000-a5f8be833748a4bcb3f8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0190000000-f93564dbf72195f07577
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-f1a9a64c5d1e03f85299
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-17067c043f8330e87007
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-2900000000-0bbeccadc1d2ba259240
MS/MS Spectrum - , positiveLC-MS/MSsplash10-002f-0290000000-ac0cf9f1a6852adb199f

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Oxazoles
Direct Parent
Phenyl-1,3-oxazoles
Alternative Parents
2,4,5-trisubstituted oxazoles / Benzene and substituted derivatives / Heteroaromatic compounds / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
Phenyl-1,3-oxazole / 2,4,5-trisubstituted 1,3-oxazole / Monocyclic benzene moiety / Benzenoid / Heteroaromatic compound / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Azacycle / Oxacycle
show 9 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
1,3-oxazoles, monocarboxylic acid (CHEBI:7822)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Kawai S: Cyclooxygenase selectivity and the risk of gastro-intestinal complications of various non-steroidal anti-inflammatory drugs: a clinical consideration. Inflamm Res. 1998 Oct;47 Suppl 2:S102-6. [PubMed:9831331]
  2. Kean WF: Oxaprozin: kinetic and dynamic profile in the treatment of pain. Curr Med Res Opin. 2004 Aug;20(8):1275-7. [PubMed:15324530]
  3. Zhou XP, Zhang MX, Sun W, Yang XH, Wang GS, Sui DY, Yu XF, Qu SC: Design, synthesis, and in-vivo evaluation of 4,5-diaryloxazole as novel nonsteroidal anti-inflammatory drug. Biol Pharm Bull. 2009 Dec;32(12):1986-90. [PubMed:19952416]
  4. Ottonello L, Bertolotto M, Montecucco F, Bianchi G, Dallegri F: Delayed apoptosis of human monocytes exposed to immune complexes is reversed by oxaprozin: role of the Akt/IkappaB kinase/nuclear factor kappaB pathway. Br J Pharmacol. 2009 May;157(2):294-306. doi: 10.1111/j.1476-5381.2009.00162.x. Epub 2009 Mar 26. [PubMed:19338579]
  5. Yood MU, Watkins E, Wells K, Kucera G, Johnson CC: The impact of NSAID or COX-2 inhibitor use on the initiation of antihypertensive therapy. Pharmacoepidemiol Drug Saf. 2006 Dec;15(12):852-60. [PubMed:17024689]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Yood MU, Watkins E, Wells K, Kucera G, Johnson CC: The impact of NSAID or COX-2 inhibitor use on the initiation of antihypertensive therapy. Pharmacoepidemiol Drug Saf. 2006 Dec;15(12):852-60. [PubMed:17024689]
  2. Kawai S, Nishida S, Kato M, Furumaya Y, Okamoto R, Koshino T, Mizushima Y: Comparison of cyclooxygenase-1 and -2 inhibitory activities of various nonsteroidal anti-inflammatory drugs using human platelets and synovial cells. Eur J Pharmacol. 1998 Apr 17;347(1):87-94. [PubMed:9650852]
  3. Kawai S: Cyclooxygenase selectivity and the risk of gastro-intestinal complications of various non-steroidal anti-inflammatory drugs: a clinical consideration. Inflamm Res. 1998 Oct;47 Suppl 2:S102-6. [PubMed:9831331]
  4. Yamazaki R, Kusunoki N, Matsuzaki T, Hashimoto S, Kawai S: Nonsteroidal anti-inflammatory drugs induce apoptosis in association with activation of peroxisome proliferator-activated receptor gamma in rheumatoid synovial cells. J Pharmacol Exp Ther. 2002 Jul;302(1):18-25. [PubMed:12065695]
  5. Zhou XP, Zhang MX, Sun W, Yang XH, Wang GS, Sui DY, Yu XF, Qu SC: Design, synthesis, and in-vivo evaluation of 4,5-diaryloxazole as novel nonsteroidal anti-inflammatory drug. Biol Pharm Bull. 2009 Dec;32(12):1986-90. [PubMed:19952416]
  6. Ottonello L, Bertolotto M, Montecucco F, Bianchi G, Dallegri F: Delayed apoptosis of human monocytes exposed to immune complexes is reversed by oxaprozin: role of the Akt/IkappaB kinase/nuclear factor kappaB pathway. Br J Pharmacol. 2009 May;157(2):294-306. doi: 10.1111/j.1476-5381.2009.00162.x. Epub 2009 Mar 26. [PubMed:19338579]

Drug created on June 13, 2005 07:24 / Updated on November 14, 2018 12:48