Piroxicam (CHEM016394)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:30:16 UTC
Update Date2016-11-09 01:15:23 UTC
Accession NumberCHEM016394
Identification
Common NamePiroxicam
ClassSmall Molecule
DescriptionA monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide with the exocyclic nitrogen of 2-aminopyridine. A non-steroidal anti-inflammatory drug of the oxicam class, it is used to relieve pain and works by preventing the production of endogenous prostaglandins involved in the mediation of pain, stiffness, tenderness and swelling.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass331.346 g/mol
Monoisotopic Mass331.063 g/mol
CAS Registry Number36322-90-4
IUPAC Name4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ⁶,2-benzothiazine-3-carboxamide
Traditional Namepiroxicam
SMILESCN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O
InChI IdentifierInChI=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
Description 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-3911000000-4ebab92e0a9daf942bf0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-2911000000-0f09e215129357f2b76dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-1000-1698000000-9bfc929b8cee2ec1d841Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00dj-6911100000-64e355e5e08c884173b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0019000000-0d247806d6203409cc16Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014j-0591000000-7d11d429795ac27fa093Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000t-0910000000-42d97ebe5da8190aa202Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001m-2900000000-32c34cd63ced296fee89Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-5900000000-1d4473d813b920140b81Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00lr-0009000000-9e65aa6e4b407ea80734Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000f-3984000000-e855ded4bfe08c600884Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-007c-3900000000-fb37337024398fe8044dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006t-9600000000-db1bff24de3a9b89b68dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00r2-9200000000-22caea8b3219419be51fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-01vk-6900000000-a75ce07d3bc58c9e773bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-5829000000-bfa87ed6f54b64fe3942Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-1000-1698000000-9bfc929b8cee2ec1d841Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00dj-6911100000-64e355e5e08c884173b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-006t-6901000000-41ed9a5326f5d54c5f9fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00l2-0930000000-471bbc619da22cd3edf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1109000000-0a5f568ccd8ec0dd21abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ed-5914000000-f68896ad0dca3bacbe4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9700000000-1b72c24a77ff99dbce05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2019000000-7caa2d44b7aec18e603dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000x-6339000000-58dcc57574d9e999f7b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9700000000-4282d1d0a308fb07b8c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0109000000-a10d4fec58f8f1308694Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00554
HMDB IDHMDB0014694
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPiroxicam
Chemspider ID10442653
ChEBI ID8249
PubChem Compound ID54676228
Kegg Compound IDC01608
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11142413
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12154043
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217