Isoxicam (CHEM018334)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:09:46 UTC
Update Date2016-11-09 01:15:47 UTC
Accession NumberCHEM018334
Identification
Common NameIsoxicam
ClassSmall Molecule
DescriptionA monocarboxylic acid amide that is piroxicam in which the pyrid-2-yl group is replaced by a 5-methyl-1,2-oxazol-3-yl group. A non-steroidal anti-inflammatory drug, it was withdrawn from the market in the 1980s following its association with cases of Stevens-Johnson syndrome.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxideChEBI
4-Hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxideChEBI
BRN 0577221ChEBI
EINECS 252-084-5ChEBI
IsoxicamoChEBI
IsoxicamumChEBI
MaxicamChEBI
N-(5-Methyl-3-isoxazolyl)-4-hydroxy-2-methyl-2H-1,2-benzthiazine-3-carboxamide 1,1-dioxideChEBI
UNII-8xu734c4NGChEBI
W 8495ChEBI
VectrenMeSH
Chemical FormulaC14H13N3O5S
Average Molecular Mass335.335 g/mol
Monoisotopic Mass335.058 g/mol
CAS Registry Number34552-84-6
IUPAC Name4-hydroxy-2-methyl-N-(5-methyl-2,3-dihydro-1,2-oxazol-3-ylidene)-1,1-dioxo-2H-1λ⁶,2-benzothiazine-3-carboxamide
Traditional Namemaxicam
SMILESCN1C(C(=O)N=C2NOC(C)=C2)=C(O)C2=CC=CC=C2S1(=O)=O
InChI IdentifierInChI=1S/C14H13N3O5S/c1-8-7-11(16-22-8)15-14(19)12-13(18)9-5-3-4-6-10(9)23(20,21)17(12)2/h3-7,18H,1-2H3,(H,15,16,19)
InChI KeyYYUAYBYLJSNDCX-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
  • Organosulfonic acid amide
  • Benzenoid
  • Azole
  • Isoxazole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Vinylogous acid
  • Heteroaromatic compound
  • N-acylimine
  • Carboxylic acid derivative
  • Azacycle
  • Oxacycle
  • Organic oxide
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • 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 Solubility0.34 g/LALOGPS
logP0.6ALOGPS
logP-0.085ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.46ChemAxon
pKa (Strongest Basic)-0.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area108.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.9 m³·mol⁻¹ChemAxon
Polarizability32.24 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-5910000000-59f2ea7557d92ab78864Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004r-3911000000-ea33aeb4c6cdbcd42af1Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0hi2-4920000000-6d8f0aecb48174d3dfd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-6139000000-eda17764d6ae14c8ea69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9100000000-6a727de849d5762b2236Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9100000000-c14c34207cdf213edad8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-3019000000-80a85d94a87f57b4278eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9114000000-b3bac29c6306d4d35c25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000e-9500000000-1aefb087b601b1c5bb27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2009000000-ceb60f900f597754c2feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-9116000000-7d5aa59172644fb2653aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9210000000-e2893be2258651b2bbacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0393000000-059648ce6bfdbc7bdc9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-4592000000-d145fec97cc1a05cdf04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0304-9660000000-20526b055b7fe2f92b6bSpectrum
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 IDDB08942
HMDB IDHMDB0253714
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIsoxicam
Chemspider ID10442695
ChEBI ID76163
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1236641
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1499594
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24061247
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2575504
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=2618088
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=3436154
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=3557542
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=3620270
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=3620275
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=3620277
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=3904436
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=3904438
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6391795