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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:14:52 UTC
HMDB IDHMDB0015126
Secondary Accession Numbers
  • HMDB15126
Metabolite Identification
Common NameOxaprozin
DescriptionOxaprozin 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, 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.
Structure
Thumb
Synonyms
ValueSource
DanoproxChEBI
DayproChEBI
DayrunChEBI
DeflamChEBI
DuraproxChEBI
OxaprozinaChEBI
OxaprozineChEBI
OxaprozinumChEBI
WalixChEBI
apo-OxaprozinMeSH
4,5-Diphenyl-2-oxazolepropionic acidMeSH
Rhoxal-oxaprozinMeSH
Chemical FormulaC18H15NO3
Average Molecular Weight293.3166
Monoisotopic Molecular Weight293.105193351
IUPAC Name3-(diphenyl-1,3-oxazol-2-yl)propanoic acid
Traditional Nameoxaprozin
CAS Registry Number21256-18-8
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 KeyOFPXSFXSNFPTHF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassOxazoles
Direct ParentPhenyl-1,3-oxazoles
Alternative Parents
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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point158 - 159 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.032 g/LNot Available
LogP3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity81.88 m³·mol⁻¹ChemAxon
Polarizability31.69 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002e-1490000000-20b13a86a35f44aa9a2aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fmj-9371000000-a881e15eec194d35556aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0090000000-a5f8be833748a4bcb3f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0190000000-f93564dbf72195f07577View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-f1a9a64c5d1e03f85299View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-17067c043f8330e87007View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-2900000000-0bbeccadc1d2ba259240View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-002f-0290000000-ac0cf9f1a6852adb199fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0090000000-388d0a348d00d079f7e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002e-1190000000-d998a751228c6dfef9bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5910000000-9045a8361d563707064bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-c41ec34e2e965c08080bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1190000000-11f9f6e42bf117dcf8d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-7940000000-51103105d7b7cd85b06dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00991 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00991 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00991
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4453
KEGG Compound IDC07356
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxaprozin
METLIN IDNot Available
PubChem Compound4614
PDB IDNot Available
ChEBI ID7822
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 ]