Ampiroxicam (CHEM019020)

Record Information
Version1.0
Creation Date2016-05-22 05:45:43 UTC
Update Date2026-08-20 05:28:39 UTC
Accession NumberCHEM019020
Identification
Common NameAmpiroxicam
ClassSmall Molecule
Description
A benzothiazine that is the 1-[(ethoxycarbonyl)oxy]ethyl ether of piroxicam. A prodrug for piroxicam, it is used for the relief of pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AmpiroxicamumChEBI
Carbonic acid ethyl 1-({2-methyl-3-[(2-pyridinylamino)carbonyl]-2H-1,2-benzothiazin-4-yl}oxy)ethyl ester S,S-dioxideChEBI
CP 65703ChEBI
CP-65703ChEBI
FlucamChEBI
Carbonate ethyl 1-({2-methyl-3-[(2-pyridinylamino)carbonyl]-2H-1,2-benzothiazin-4-yl}oxy)ethyl ester S,S-dioxideGenerator
Chemical FormulaC20H21N3O7S
Average Molecular Mass447.460 g/mol
Monoisotopic Mass447.110 g/mol
CAS Registry Number99464-64-9
IUPAC Name4-{1-[(ethoxycarbonyl)oxy]ethoxy}-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ⁶,2-benzothiazine-3-carboximidic acid
Traditional Nameampiroxicam
SMILESCCOC(=O)OC(C)OC1=C(N(C)S(=O)(=O)C2=CC=CC=C12)C(O)=NC1=CC=CC=N1
InChI IdentifierInChI=1S/C20H21N3O7S/c1-4-28-20(25)30-13(2)29-18-14-9-5-6-10-15(14)31(26,27)23(3)17(18)19(24)22-16-11-7-8-12-21-16/h5-13H,4H2,1-3H3,(H,21,22,24)
InChI KeyLSNWBKACGXCGAJ-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
  • N-arylamide
  • Ortho-thiazine
  • Carbonic acid diester
  • Pyridine
  • Imidolactam
  • Benzenoid
  • Organosulfonic acid amide
  • Heteroaromatic compound
  • Organic sulfonic acid or derivatives
  • Vinylogous ester
  • Organosulfonic acid or derivatives
  • Carboxamide group
  • Carbonic acid derivative
  • Secondary carboxylic acid amide
  • Acetal
  • Carboxylic acid derivative
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • 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 Solubility0.038 g/LALOGPS
logP2.52ALOGPS
logP2.68ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
pKa (Strongest Basic)2.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area127.62 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity114.02 m³·mol⁻¹ChemAxon
Polarizability43.4 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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
External Links
DrugBank IDNot Available
HMDB IDHMDB0248361
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAmpiroxicam
Chemspider ID2091
ChEBI ID31210
PubChem Compound ID2176
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=10527378
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11469844
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=2219958
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=8304243
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=8730175
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=9529571
7. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.