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Record Information
Version2.0
Created at2022-09-04 19:42:00 UTC
Updated at2022-09-04 19:42:00 UTC
NP-MRD IDNP0200784
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-hydroxy-2-methyl-n-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1λ⁶,2-benzothiazine-3-carboximidic acid
DescriptionMeloxicam, also known as mobic or unii-VG2QF83CGL, 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). Meloxicam is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, meloxicam is involved in meloxicam action pathway. 4-hydroxy-2-methyl-n-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1λ⁶,2-benzothiazine-3-carboximidic acid is found in Apis cerana. 4-hydroxy-2-methyl-n-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1λ⁶,2-benzothiazine-3-carboximidic acid was first documented in 1999 (PMID: 10092958). Meloxicam is a potentially toxic compound (PMID: 12387696) (PMID: 16197363) (PMID: 16623613) (PMID: 16863437).
Structure
Thumb
Synonyms
ValueSource
MeloxicamumChEBI
MobicChEBI
UNII-VG2QF83CGLChEBI
MasflexHMDB
MobicoxHMDB
MovalisHMDB
MovicoxHMDB
MobecHMDB
UticoxHMDB
ParocinHMDB
MiloxicamHMDB
ReumoxicamHMDB
Chemical FormulaC14H13N3O4S2
Average Mass351.4010 Da
Monoisotopic Mass351.03475 Da
IUPAC Name4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1λ⁶,2-benzothiazine-3-carboxamide
Traditional Namemeloxicam
CAS Registry NumberNot Available
SMILES
CN1C(C(=O)NC2=NC=C(C)S2)=C(O)C2=C(C=CC=C2)S1(=O)=O
InChI Identifier
InChI=1S/C14H13N3O4S2/c1-8-7-15-14(22-8)16-13(19)11-12(18)9-5-3-4-6-10(9)23(20,21)17(11)2/h3-7,18H,1-2H3,(H,15,16,19)
InChI KeyZRVUJXDFFKFLMG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
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
  • 2,5-disubstituted 1,3-thiazole
  • Ortho-thiazine
  • Benzenoid
  • Organosulfonic acid amide
  • Azole
  • Heteroaromatic compound
  • Vinylogous acid
  • Thiazole
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.28ALOGPS
logP1.6ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.47ChemAxon
pKa (Strongest Basic)0.47ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.62 m³·mol⁻¹ChemAxon
Polarizability34.25 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0014952
DrugBank IDDB00814
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10442740
KEGG Compound IDC08169
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMeloxicam
METLIN IDNot Available
PubChem Compound54677470
PDB IDNot Available
ChEBI ID6741
Good Scents IDNot Available
References
General References
  1. Davies NM, Skjodt NM: Clinical pharmacokinetics of meloxicam. A cyclo-oxygenase-2 preferential nonsteroidal anti-inflammatory drug. Clin Pharmacokinet. 1999 Feb;36(2):115-26. doi: 10.2165/00003088-199936020-00003. [PubMed:10092958 ]
  2. Fleischmann R, Iqbal I, Slobodin G: Meloxicam. Expert Opin Pharmacother. 2002 Oct;3(10):1501-12. doi: 10.1517/14656566.3.10.1501. [PubMed:12387696 ]
  3. Gates BJ, Nguyen TT, Setter SM, Davies NM: Meloxicam: a reappraisal of pharmacokinetics, efficacy and safety. Expert Opin Pharmacother. 2005 Oct;6(12):2117-40. doi: 10.1517/14656566.6.12.2117. [PubMed:16197363 ]
  4. Curtiss FR: Relative value of the NSAIDs, including COX-2 inhibitors and meloxicam. J Manag Care Pharm. 2006 Apr;12(3):265-8. doi: 10.18553/jmcp.2006.12.3.265. [PubMed:16623613 ]
  5. Ahmed M, Khanna D, Furst DE: Meloxicam in rheumatoid arthritis. Expert Opin Drug Metab Toxicol. 2005 Dec;1(4):739-51. doi: 10.1517/17425255.1.4.739. [PubMed:16863437 ]
  6. LOTUS database [Link]