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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-03-02 21:33:24 UTC
HMDB IDHMDB14694
Secondary Accession NumbersNone
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
Synonyms
ValueSource
4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxidChEBI
FeldeneChEBI
PiroxicamumChEBI
PyroxycamChEBI
AK1015HMDB
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
DescriptionThis compound belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassNot Available
Direct ParentBenzothiazines
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Benzothiazine
  • Ortho-thiazine
  • Pyridine
  • Organosulfonic acid amide
  • Benzenoid
  • Imidolactam
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboximidic acid
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Cyclooxygenase Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point198 - 200 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.43e-01 g/LNot Available
LogP3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity87.04 m3·mol-1ChemAxon
Polarizability32.27 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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-ITFT , 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, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Piroxicam PathwaySMP00077Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00554
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00554
  • Not Applicable
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
NuGOwiki LinkHMDB14694
Metagene LinkHMDB14694
METLIN IDNot Available
PubChem Compound54676228
PDB IDNot Available
ChEBI ID8249
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available