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Showing drug card for Oxaprozin (DB00991)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:07:42
Primary Accession Number DB00991
Secondary Accession Number
  • APRD00030
Name Oxaprozin
Drug Type
  • Approved
  • Small Molecule
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.
Synonyms
  1. Oxaprozina [INN-Spanish]
  2. Oxaprozine [INN-French]
  3. Oxaprozinum [INN-Latin]
Brand Names
  1. Alvo
  2. Daypro
  3. Daypro Alta
  4. Deflam
  5. Voir
Brand Mixtures Not Available
Chemical IUPAC Name 3-[4,5-di(phenyl)-1,3-oxazol-2-yl]propanoic acid
Chemical Formula C18H15NO3
Chemical Structure Structure
CAS Registry Number 21256-18-8
InChI Identifier InChI=1/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)/f/h20H
InChI Key OFPXSFXSNFPTHF-UYBDAZJACQ
KEGG Drug D00463 Link Image
KEGG Compound C07356 Link Image
PubChem Compound 4614 Link Image
PubChem Substance 172661 Link Image
ChEBI ID Not Available
PharmGKB ID PA450730 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02243661 Link Image
RxList Link http://www.rxlist.com/cgi/generic/oxaproz.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Oxaprozin Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 293.3166
Monoisotopic Molecular Weight 293.1052
State Solid
Melting Point 158 - 159 oC
Experimental Water Solubility Insoluble Source: PhysProp
Predicted Water Solubility 3.25e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3.7 Source: PhysProp
Predicted LogP 3.33 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.96 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point 4.3
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES OC(=O)CCC1=NC(C2=CC=CC=C2)=C(O1)C1=CC=CC=C1
Canonical SMILES OC(=O)CCC1=NC(C2=CC=CC=C2)=C(O1)C1=CC=CC=C1
Drug Category
  • Anti-Inflammatory Agents, Non-Steroidal
  • Anti-inflammatory Agents
  • Nonsteroidal Antiinflammatory Agents (NSAIDs)
ATC Codes
AHFS Codes
  • 28:08.04.92
Indication Used to relieve the inflammation, swelling, stiffness, and joint pain associated with rheumatoid arthritis and osteoarthritis.
Pharmacology Oxaprozin is a nonsteroidal antiinflammatory drug (NSAID) with analgesic and antipyretic properties. Oxaprozin is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and to alleviate moderate pain.
Mechanism of Action Antiinflammatory 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.
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.
Toxicity Oral, mouse: LD50 = 1210 mg/kg; Oral, rabbit: LD50 = 172 mg/kg; Oral, rat: LD50 = 4470 mg/kg
Protein Binding 99%
Biotransformation Hepatic. Ester and ether glucuronide are the major conjugated metabolites of oxaprozin, and do not have significant pharmacologic activity.
Half Life 54.9 hours
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acenocoumarol The NSAID increases the anticoagulant effect
Alendronate Increased risk of gastric toxicity
Anisindione The NSAID increases the anticoagulant effect
Cyclosporine Monitor for nephrotoxicity
Dicumarol The NSAID increases the anticoagulant effect
Methotrexate The NSAID increases the effect and toxicity of methotrexate
Warfarin The NSAID increases the anticoagulant effect
Food Interactions
  • Take with food, usually once a day after breakfast. Food decreases the rate of absorption but not the amount absorbed. Avoid alcohol.
Pathways
Name SMPDB Link KEGG Link
Oxaprozin Pathway SMP00113 Link Image
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Prostaglandin G/H synthase 2
Drug Target 1 [top]
Target 1 ID 290
Target 1 Name Prostaglandin G/H synthase 2
Target 1 Synonyms
  1. COX-2
  2. Cyclooxygenase- 2
  3. EC 1.14.99.1
  4. PGH synthase 2
  5. PGHS-2
  6. PHS II
  7. Prostaglandin G/H synthase 2 precursor
  8. Prostaglandin H2 synthase 2
  9. Prostaglandin-endoperoxide synthase 2
Target 1 Gene Name PTGS2
Target 1 Protein Sequence >Prostaglandin G/H synthase 2 precursor 
MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFYGENCSTPEFL
TRIKLFLKPTPNTVHYILTHFKGFWNVVNNIPFLRNAIMSYVLTSRSHLIDSPPTYNADY
GYKSWEAFSNLSYYTRALPPVPDDCPTPLGVKGKKQLPDSNEIVEKLLLRRKFIPDPQGS
NMMFAFFAQHFTHQFFKTDHKRGPAFTNGLGHGVDLNHIYGETLARQRKLRLFKDGKMKY
QIIDGEMYPPTVKDTQAEMIYPPQVPEHLRFAVGQEVFGLVPGLMMYATIWLREHNRVCD
VLKQEHPEWGDEQLFQTSRLILIGETIKIVIEDYVQHLSGYHFKLKFDPELLFNKQFQYQ
NRIAAEFNTLYHWHPLLPDTFQIHDQKYNYQQFIYNNSILLEHGITQFVESFTRQIAGRV
AGGRNVPPAVQKVSQASIDQSRQMKYQSFNEYRKRFMLKPYESFEELTGEKEMSAELEAL
YGDIDAVELYPALLVEKPRPDAIFGETMVEVGAPFSLKGLMGNVICSPAYWKPSTFGGEV
GFQIINTASIQSLICNNVKGCPFTSFSVPDPELIKTVTINASSSRSGLDDINPTVLLKER
STEL
Target 1 Number of Residues 614
Target 1 Molecular Weight 68997
Target 1 Theoretical pI 7.41
Target 1 GO Classification
Function
antioxidant activity
peroxidase activity
Process
Not Available
Component
Not Available
Target 1 General Function Involved in peroxidase activity
Target 1 Specific Function May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity
Target 1 Pathways
Name SMPDB Link KEGG Link
Prostaglandin and leukotriene metabolism map00590 Link Image
Target 1 Reactions
  • arachidonate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-17
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 291988 Link Image
Target 1 UniProtKB/Swiss-Prot ID P35354 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name PGH2_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Microsome
  • microsomal membrane
  • peripheral membrane protein
Target 1 Gene Sequence >1815 bp 
ATGCTCGCCCGCGCCCTGCTGCTGTGCGCGGTCCTGGCGCTCAGCCATACAGCAAATCCT
TGCTGTTCCCACCCATGTCAAAACCGAGGTGTATGTATGAGTGTGGGATTTGACCAGTAT
AAGTGCGATTGTACCCGGACAGGATTCTATGGAGAAAACTGCTCAACACCGGAATTTTTG
ACAAGAATAAAATTATTTCTGAAACCCACTCCAAACACAGTGCACTACATACTTACCCAC
TTCAAGGGATTTTGGAACGTTGTGAATAACATTCCCTTCCTTCGAAATGCAATTATGAGT
TATGTGTTGACATCCAGATCACATTTGATTGACAGTCCACCAACTTACAATGCTGACTAT
GGCTACAAAAGCTGGGAAGCCTTCTCTAACCTCTCCTATTATACTAGAGCCCTTCCTCCT
GTGCCTGATGATTGCCCGACTCCCTTGGGTGTCAAAGGTAAAAAGCAGCTTCCTGATTCA
AATGAGATTGTGGAAAAATTGCTTCTAAGAAGAAAGTTCATCCCTGATCCCCAGGGCTCA
AACATGATGTTTGCATTCTTTGCCCAGCACTTCACGCATCAGTTTTTCAAGACAGATCAT
AAGCGAGGGCCAGCTTTCACCAACGGGCTGGGCCATGGGGTGGACTTAAATCATATTTAC
GGTGAAACTCTGGCTAGACAGCGTAAACTGCGCCTTTTCAAGGATGGAAAAATGAAATAT
CAGATAATTGATGGAGAGATGTATCCTCCCACAGTCAAAGATACTCAGGCAGAGATGATC
TACCCTCCTCAAGTCCCTGAGCATCTACGGTTTGCTGTGGGGCAGGAGGTCTTTGGTCTG
GTGCCTGGTCTGATGATGTATGCCACAATCTGGCTGCGGGAACACAACAGAGTATGCGAT
GTGCTTAAACAGGAGCATCCTGAATGGGGTGATGAGCAGTTGTTCCAGACAAGCAGGCTA
ATACTGATAGGAGAGACTATTAAGATTGTGATTGAAGATTATGTGCAACACTTGAGTGGC
TATCACTTCAAACTGAAATTTGACCCAGAACTACTTTTCAACAAACAATTCCAGTACCAA
AATCGTATTGCTGCTGAATTTAACACCCTCTATCACTGGCATCCCCTTCTGCCTGACACC
TTTCAAATTCATGACCAGAAATACAACTATCAACAGTTTATCTACAACAACTCTATATTG
CTGGAACATGGAATTACCCAGTTTGTTGAATCATTCACCAGGCAAATTGCTGGCAGGGTT
GCTGGTGGTAGGAATGTTCCACCCGCAGTACAGAAAGTATCACAGGCTTCCACTGACCAG
AGCAGGCAGATGAAATACCAGTCTTTTAATGAGTACCGCAAACGCTTTATGCTGAAGCCC
TATGAATCATTTGAAGAACTTACAGGAGAAAAGGAAATGTCTGCAGAGTTGGAAGCACTC
TATGGTGACATCGATGCTGTGGAGCTGTATCCTGCCCTTCTGGTAGAAAAGCCTCGGCCA
GATGCCATCTTTGGTGAAACCATGGTAGAAGTTGGAGCACCATTCTCCTTGAAAGGACTT
ATGGGTAATGTTATATGTTCTCCTGCCTACTGGAAGCCAAGCACTTTTGGTGGAGAAGTG
GGTTTTCAAATCATCAACACTGCCTCAATTCAGTCTCTCATCTGCAATAACGTGAAGGGC
TGTCCCTTTACTTCATTCAGTGTTCCAGATCCAGAGCTCATTAAAACAGTCACCATCAAT
GCAAGTTCTTCCCGCTCCGGACTAGATGATATCAATCCCACAGTACTACTAAAAGAACGT
TCGACTGAACTGTAG
Target 1 GenBank Gene ID
Target 1 GeneCard ID PTGS2 Link Image
Target 1 GenAtlas ID PTGS2 Link Image
Target 1 HGNC ID HGNC:9605 Link Image
Target 1 Chromosome Location 1
Target 1 Locus 1q25.2-q25.3
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Hla T, Neilson K: Human cyclooxygenase-2 cDNA. Proc Natl Acad Sci U S A. 1992 Aug 15;89(16):7384-8. [PubMed Link Image]
  2. Appleby SB, Ristimaki A, Neilson K, Narko K, Hla T: Structure of the human cyclo-oxygenase-2 gene. Biochem J. 1994 Sep 15;302 ( Pt 3):723-7. [PubMed Link Image]
  3. Kosaka T, Miyata A, Ihara H, Hara S, Sugimoto T, Takeda O, Takahashi E, Tanabe T: Characterization of the human gene (PTGS2) encoding prostaglandin-endoperoxide synthase 2. Eur J Biochem. 1994 May 1;221(3):889-97. [PubMed Link Image]
  4. Jones DA, Carlton DP, McIntyre TM, Zimmerman GA, Prescott SM: Molecular cloning of human prostaglandin endoperoxide synthase type II and demonstration of expression in response to cytokines. J Biol Chem. 1993 Apr 25;268(12):9049-54. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. 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 Link Image]
  3. 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 Link Image]
  4. 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 Link Image]
  5. Rothstein R: Safety profiles of leading nonsteroidal anti-inflammatory drugs. Am J Med. 1998 Nov 2;105(5A):39S-43S. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.