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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-10-23 19:06:21 UTC
HMDB IDHMDB0014694
Secondary Accession Numbers
  • HMDB14694
Metabolite Identification
Common NamePiroxicam
DescriptionPiroxicam is only found in individuals that have used or taken this drug. It is a cyclooxygenase inhibiting, non-steroidal anti-inflammatory agent (NSAID) that is well established in treating rheumatoid arthritis and osteoarthritis and used for musculoskeletal disorders, dysmenorrhea, and postoperative pain. Its long half-life enables it to be administered once daily. [PubChem]The antiinflammatory effect of Piroxicam may result from the reversible inhibition of cyclooxygenase, causing the peripheral inhibition of prostaglandin synthesis. The prostaglandins are produced by an enzyme called Cox-1. Piroxicam blocks the Cox-1 enzyme, resulting into the disruption of production of prostaglandins. Piroxicam also inhibits the migration of leukocytes into sites of inflammation and prevents the formation of thromboxane A2, an aggregating agent, by the platelets.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H13N3O4S
Average Molecular Weight331.346
Monoisotopic Molecular Weight331.062676609
IUPAC Name4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ⁶,2-benzothiazine-3-carboxamide
Traditional Namepiroxicam
CAS Registry Number36322-90-4
SMILES
CN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O
InChI Identifier
InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)
InChI KeyQYSPLQLAKJAUJT-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point198 - 200 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.14 g/LNot Available
LogP3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.2ALOGPS
logP0.6ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.76ChemAxon
pKa (Strongest Basic)3.79ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity87.04 m³·mol⁻¹ChemAxon
Polarizability32.27 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, Positivesplash10-014i-3911000000-4ebab92e0a9daf942bf0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-2911000000-0f09e215129357f2b76dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-1000-1698000000-9bfc929b8cee2ec1d841View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00dj-6911100000-64e355e5e08c884173b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0019000000-0d247806d6203409cc16View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014j-0591000000-7d11d429795ac27fa093View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000t-0910000000-42d97ebe5da8190aa202View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001m-2900000000-32c34cd63ced296fee89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-5900000000-1d4473d813b920140b81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00lr-0009000000-9e65aa6e4b407ea80734View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000f-3984000000-e855ded4bfe08c600884View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-007c-3900000000-fb37337024398fe8044dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006t-9600000000-db1bff24de3a9b89b68dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00r2-9200000000-22caea8b3219419be51fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-01vk-6900000000-a75ce07d3bc58c9e773bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-5829000000-bfa87ed6f54b64fe3942View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-1000-1698000000-9bfc929b8cee2ec1d841View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00dj-6911100000-64e355e5e08c884173b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1109000000-0a5f568ccd8ec0dd21abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ed-5914000000-f68896ad0dca3bacbe4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9700000000-1b72c24a77ff99dbce05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2019000000-7caa2d44b7aec18e603dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000x-6339000000-58dcc57574d9e999f7b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9700000000-4282d1d0a308fb07b8c9View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Piroxicam PathwayPw000125Pw000125 greyscalePw000125 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00554 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00554 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00554
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10442653
KEGG Compound IDC01608
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiroxicam
METLIN IDNot Available
PubChem Compound54676228
PDB IDNot Available
ChEBI ID8249
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available