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Oxaprozin

July 24, 2017
Common Name

Oxaprozin Description

Oxaprozin is only found in individuals that have used or taken this drug. It 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.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, resliting 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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source DanoproxChEBI DayproChEBI DayrunChEBI DeflamChEBI DuraproxChEBI OxaprozinaChEBI OxaprozineChEBI OxaprozinumChEBI WalixChEBI apo-OxaprozinMeSH 4,5-Diphenyl-2-oxazolepropionic acidMeSH Rhoxal-oxaprozinMeSH

Chemical Formlia

C18H15NO3 Average Molecliar Weight

293.3166 Monoisotopic Molecliar Weight

293.105193351 IUPAC Name

3-(diphenyl-1,3-oxazol-2-yl)propanoic acid Traditional Name

oxaprozin CAS Registry Number

21256-18-8 SMILES

OC(=O)CCC1=NC(=C(O1)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

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)

InChI Key

OFPXSFXSNFPTHF-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Azoles 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
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • 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
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • 1,3-oxazoles (CHEBI:7822 )
  • monocarboxylic acid (CHEBI:7822 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-inflammatory Agents
  • Nonsteroidal Anti-inflammatory Agents (NSAIAs)

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point158 – 159 °CNot Available Boiling PointNot AvailableNot Available Water Solubility3.25e-02 g/LNot Available LogP3.7Not Available

    Predicted Properties

    Property Value Source Water Solubility0.033 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0006-0090000000-a5f8be833748a4bcb3f8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-004i-0190000000-f93564dbf72195f07577View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0udi-0900000000-f1a9a64c5d1e03f85299View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0udi-0900000000-17067c043f8330e87007View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0udi-2900000000-0bbeccadc1d2ba259240View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Oxaprozin PathwaySMP00113Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00991

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00991

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00991 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4453 KEGG Compound ID

    C07356 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Oxaprozin NuGOwiki Link

    HMDB15126 Metagene Link

    HMDB15126 METLIN ID

    Not Available PubChem Compound

    4614 PDB ID

    Not Available ChEBI ID

    239225

    Product: AVX 13617

    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:http://www.ncbi.nlm.nih.gov/pubmed/19952416 Material Safety Data Sheet (MSDS) Not Available 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 ]

    Enzymes

    General function:
    Involved in peroxidase activity
    Specific function:
    Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
    Gene Name:
    PTGS2
    Uniprot ID:
    P35354
    Molecular weight:
    68995.625
    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 ]
    General function:
    Involved in peroxidase activity
    Specific function:
    May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
    Gene Name:
    PTGS1
    Uniprot ID:
    P23219
    Molecular weight:
    68685.82
    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 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
    Gene Name:
    CYP2C9
    Uniprot ID:
    P11712
    Molecular weight:
    55627.365
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

    PMID: 11463859

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