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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:42 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
Data?1582753209
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
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
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point198 - 200 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.14 g/LNot Available
LogP3Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM170.930932474
[M+H]+Not Available170.677http://allccs.zhulab.cn/database/detail?ID=AllCCS00000980
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.94731661259
DarkChem[M-H]-170.99231661259
DeepCCS[M+H]+168.64430932474
DeepCCS[M-H]-166.28630932474
DeepCCS[M-2H]-199.41730932474
DeepCCS[M+Na]+174.73730932474
AllCCS[M+H]+176.332859911
AllCCS[M+H-H2O]+172.932859911
AllCCS[M+NH4]+179.332859911
AllCCS[M+Na]+180.232859911
AllCCS[M-H]-172.732859911
AllCCS[M+Na-2H]-172.332859911
AllCCS[M+HCOO]-172.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PiroxicamCN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O4575.1Standard polar33892256
PiroxicamCN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O2558.7Standard non polar33892256
PiroxicamCN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O2835.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Piroxicam,1TMS,isomer #1CN1C(C(=O)NC2=CC=CC=N2)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O2835.3Semi standard non polar33892256
Piroxicam,1TMS,isomer #2CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O2772.1Semi standard non polar33892256
Piroxicam,2TMS,isomer #1CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O2758.1Semi standard non polar33892256
Piroxicam,2TMS,isomer #1CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O2912.3Standard non polar33892256
Piroxicam,2TMS,isomer #1CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O3833.8Standard polar33892256
Piroxicam,1TBDMS,isomer #1CN1C(C(=O)NC2=CC=CC=N2)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O3054.1Semi standard non polar33892256
Piroxicam,1TBDMS,isomer #2CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O2995.4Semi standard non polar33892256
Piroxicam,2TBDMS,isomer #1CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O3149.5Semi standard non polar33892256
Piroxicam,2TBDMS,isomer #1CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O3375.6Standard non polar33892256
Piroxicam,2TBDMS,isomer #1CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O3894.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Piroxicam GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-3911000000-4ebab92e0a9daf942bf02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Piroxicam GC-MS (1 TMS) - 70eV, Positivesplash10-014i-2911000000-0f09e215129357f2b76d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Piroxicam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Piroxicam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-qTof , Positive-QTOFsplash10-1000-1698000000-9bfc929b8cee2ec1d8412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-qTof , Positive-QTOFsplash10-00dj-6911100000-64e355e5e08c884173b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , negative-QTOFsplash10-001i-0019000000-0d247806d6203409cc162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , negative-QTOFsplash10-014j-0591000000-7d11d429795ac27fa0932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , negative-QTOFsplash10-000t-0910000000-42d97ebe5da8190aa2022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , negative-QTOFsplash10-001m-2900000000-32c34cd63ced296fee892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , negative-QTOFsplash10-00kf-5900000000-1d4473d813b920140b812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , positive-QTOFsplash10-00lr-0009000000-9e65aa6e4b407ea807342017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , positive-QTOFsplash10-000f-3984000000-e855ded4bfe08c6008842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , positive-QTOFsplash10-007c-3900000000-fb37337024398fe8044d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , positive-QTOFsplash10-006t-9600000000-db1bff24de3a9b89b68d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , positive-QTOFsplash10-00r2-9200000000-22caea8b3219419be51f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam LC-ESI-IT , positive-QTOFsplash10-01vk-6900000000-a75ce07d3bc58c9e773b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam , positive-QTOFsplash10-001i-5829000000-bfa87ed6f54b64fe39422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam , positive-QTOFsplash10-1000-1698000000-9bfc929b8cee2ec1d8412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam , positive-QTOFsplash10-00dj-6911100000-64e355e5e08c884173b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam 35V, Positive-QTOFsplash10-006t-6901000000-41ed9a5326f5d54c5f9f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Piroxicam 35V, Negative-QTOFsplash10-00l2-0930000000-471bbc619da22cd3edf42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piroxicam 10V, Positive-QTOFsplash10-001i-1109000000-0a5f568ccd8ec0dd21ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piroxicam 20V, Positive-QTOFsplash10-00ed-5914000000-f68896ad0dca3bacbe4c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piroxicam 40V, Positive-QTOFsplash10-00di-9700000000-1b72c24a77ff99dbce052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piroxicam 10V, Negative-QTOFsplash10-001i-2019000000-7caa2d44b7aec18e603d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piroxicam 20V, Negative-QTOFsplash10-000x-6339000000-58dcc57574d9e999f7b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piroxicam 40V, Negative-QTOFsplash10-0006-9700000000-4282d1d0a308fb07b8c92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piroxicam 10V, Positive-QTOFsplash10-001i-0109000000-a10d4fec58f8f13086942021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00554 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00554 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00554
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available