Oxaprozin

Identification

Summary

Oxaprozin is an NSAID used to treat osteoarthritis, rheumatoid arthritis, and juvenile rheumatoid arthritis.

Brand Names
Coxanto, Daypro
Generic Name
Oxaprozin
DrugBank Accession Number
DB00991
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 293.3166
Monoisotopic: 293.105193351
Chemical Formula
C18H15NO3
Synonyms
  • Oxaprozin
  • Oxaprozina
  • Oxaprozine
  • Oxaprozinum
External IDs
  • WY-21,743
  • WY-21743

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofJuvenile rheumatoid arthritis••••••••••••
Symptomatic treatment ofOsteoarthritis••••••••••••
Symptomatic treatment ofRheumatoid arthritis••••••••••••
Contraindications & Blackbox Warnings
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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
Humans
AProstaglandin G/H synthase 2
inhibitor
Humans
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

Adverse Effects
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Toxicity

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

Pathways
PathwayCategory
Oxaprozin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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.
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.
Food Interactions
  • Take with food. Take once daily after breakfast. Food decreases the rate but not the extent of absorption.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Oxaprozin potassiumML56O2Z92I174064-08-5QTAQWNSMRSLSCG-UHFFFAOYSA-M
Product Images
International/Other Brands
Alvo / Danoprox / Dayrun / Deflam / Duraprox / Walix
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CoxantoCapsule300 mg/1OralSolubiomix, LLC2023-10-24Not applicableUS flag
DayproTablet600 mgOralPfizer Canada Ulc1997-01-072012-09-20Canada flag
DayproTablet, film coated600 mg/1OralPfizer Laboratories Div Pfizer Inc1992-10-29Not applicableUS flag
DayproTablet, film coated600 mg/1OralPD-Rx Pharmaceuticals, Inc.1992-10-29Not applicableUS flag
DayproTablet, film coated600 mg/1OralPhysicians Total Care, Inc.1992-10-292010-06-30US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-oxaprozinTablet600 mgOralApotex Corporation2001-05-292018-04-26Canada flag
OxaprozinTablet, film coated600 mg/1OralGreenstone LLC2013-03-27Not applicableUS flag
OxaprozinTablet, film coated600 mg/1OralA-S Medication Solutions2001-01-31Not applicableUS flag
OxaprozinTablet600 mg/1OralChartwell Rx, Llc.2004-09-02Not applicableUS flag
OxaprozinTablet, film coated600 mg/1OralTeva Pharmaceuticals USA, Inc.2003-05-12Not applicableUS flag

Categories

ATC Codes
M01AE12 — Oxaprozin
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
2,4,5-trisubstituted 1,3-oxazole / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Monocarboxylic acid or derivatives
show 9 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
1,3-oxazoles, monocarboxylic acid (CHEBI:7822)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
MHJ80W9LRB
CAS number
21256-18-8
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-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic acid
SMILES
OC(=O)CCC1=NC(=C(O1)C1=CC=CC=C1)C1=CC=CC=C1

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. [Article]
Human Metabolome Database
HMDB0015126
KEGG Drug
D00463
KEGG Compound
C07356
PubChem Compound
4614
PubChem Substance
46506429
ChemSpider
4453
BindingDB
50002861
RxNav
32613
ChEBI
7822
ChEMBL
CHEMBL1071
ZINC
ZINC000049643479
Therapeutic Targets Database
DAP000622
PharmGKB
PA450730
PDBe Ligand
BJ6
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Oxaprozin
PDB Entries
7xc4
FDA label
Download (47 KB)
MSDS
Download (63.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers (HV)1

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
CapsuleOral300 mg/1
TabletOral600 mg
Tablet, film coatedOral
Tablet, coatedOral600 mg
TabletOral600 mg/1
Tablet, film coatedOral600 mg/1
Tablet, film coatedOral600 mg
TabletOral
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)Region
US6030643No2000-02-292017-05-16US flag

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-MSsplash10-002e-1490000000-20b13a86a35f44aa9a2a
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-0090000000-34f5f646e550d6811b9d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-bbadb6719fcca1f43b19
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dj-0090000000-9c0474f71d197c43d7ac
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-5910000000-0193ea3f58c4a46cbf3d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dm-0980000000-929c79b5da9e4a48b081
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1910000000-3e29c94148f3e064a343
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-182.7003606
predicted
DarkChem Lite v0.1.0
[M-H]-182.7105606
predicted
DarkChem Lite v0.1.0
[M-H]-164.16786
predicted
DeepCCS 1.0 (2019)
[M+H]+184.1886606
predicted
DarkChem Lite v0.1.0
[M+H]+183.9830606
predicted
DarkChem Lite v0.1.0
[M+H]+166.52586
predicted
DeepCCS 1.0 (2019)
[M+Na]+183.2406606
predicted
DarkChem Lite v0.1.0
[M+Na]+183.0714606
predicted
DarkChem Lite v0.1.0
[M+Na]+172.619
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. [Article]
  2. Kean WF: Oxaprozin: kinetic and dynamic profile in the treatment of pain. Curr Med Res Opin. 2004 Aug;20(8):1275-7. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48