MELOXICAM

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC M01AC06
UNII VG2QF83CGL
EPA CompTox DTXSID1020803

Structure

InChI Key ZRVUJXDFFKFLMG-UHFFFAOYSA-N
Smiles Cc1cnc(NC(=O)C2=C(O)c3ccccc3S(=O)(=O)N2C)s1
InChI
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H13N3O4S2
Molecular Weight 351.41
AlogP 1.95
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 99.6
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 23.0

Bioactivity

Mechanism of Action Action Reference
Cyclooxygenase-2 inhibitor INHIBITOR PubMed
Protein: Cyclooxygenase-2
Description: Prostaglandin G/H synthase 2
Organism : Homo sapiens
P35354 ENSG00000073756
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 1400-85800 - - -7-39
Epigenetic regulator Writer Protein methyltransferase SET domain
- - - - 18-29
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 77500 - - -
Assay Description Organism Bioactivity Reference
Inhibition of human Prostaglandin G/H synthase 2 at 0.1 ug/mL expressed as mean percent inhibition of control PGE-2 production None 24.0 %
Inhibition of human Prostaglandin G/H synthase 2 at 1 ug/mL expressed as mean percent inhibition of control PGE-2 production None 72.0 %
Inhibition of human Prostaglandin G/H synthase 2 at 10 ug/mL expressed as mean percent inhibition of control PGE-2 production None 77.0 %
Inhibitory activity against Prostaglandin G/H synthase 1 in Microsomal assay at dose 0.1 ug/mL Cercopithecidae -7.0 %
Inhibitory activity against Prostaglandin G/H synthase 1 in Microsomal assay at dose 1 ug/ml Cercopithecidae -1.0 %
Inhibitory activity against Prostaglandin G/H synthase 1 in Microsomal assay at dose 10 ug/ml Cercopithecidae 39.0 %
Inhibition of human Prostaglandin G/H synthase 1 at 0.1 ug/mL expressed as mean percent inhibition of control PGE-2 production None -7.0 %
Inhibition of human Prostaglandin G/H synthase 1 at 1 ug/mL expressed as mean percent inhibition of control PGE-2 production None -1.0 %
Inhibition of human Prostaglandin G/H synthase 1 at 10 ug/mL expressed as mean percent inhibition of control PGE-2 production None 39.0 %
Concentration that caused a 50% decrease in the maximal inhibition of Prostaglandin G/H synthase 2 activity as measured by PGE-2 production. Cercopithecidae 160.0 nM
Inhibitory activity against Prostaglandin G/H synthase 2 in Microsomal assay at dose 0.1 ug/mL Cercopithecidae 24.0 %
Inhibitory activity against Prostaglandin G/H synthase 2 in Microsomal assay at dose 1 ug/ml Cercopithecidae 72.0 %
Inhibitory activity against Prostaglandin G/H synthase 2 in Microsomal assay at dose 10 ug/ml Cercopithecidae 77.0 %
Concentration of drug that causes a 50% decrease in the maximal inhibition of Prostaglandin G/H synthase 2 activity as measured by PGE-2 production None 490.0 nM
In vitro inhibitory activity against human whole blood Prostaglandin G/H synthase 2 Homo sapiens 700.0 nM
Antiinflammatory activity in the carrageenan paw edema model at a dose of 30 mg/kg. Rattus norvegicus 56.0 %
Inhibition of TxB2 production in human blood at 15 mg, po after 48 hrs by enzyme immunoassay pretreated with itraconazole at 200 mg, po qd for 4 days Homo sapiens 29.0 %
Inhibition of TxB2 production in human blood at 15 mg, po after 5 hrs by enzyme immunoassay Homo sapiens 30.0 %
Inhibition of TxB2 production in human blood at 15 mg, po after 8 hrs by enzyme immunoassay Homo sapiens 37.0 %
Inhibition of TxB2 production in human blood at 15 mg, po after 12 hrs by enzyme immunoassay Homo sapiens 56.0 %
Inhibition of TxB2 production in human blood at 15 mg, po after 24 hrs by enzyme immunoassay Homo sapiens 28.0 %
Inhibition of TxB2 production in human blood at 15 mg, po after 48 hrs by enzyme immunoassay Homo sapiens 25.0 %
DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) None 938.0 nM
Antiinflammatory activity in Sprague-Dawley rat assessed as inhibition of carrageenan-induced paw edema at 80 mg/kg, po administered 30 mins prior to carrageenan challenge measured at 1 hr by plethysmometer Rattus norvegicus 20.8 %
Antiinflammatory activity in Sprague-Dawley rat assessed as inhibition of carrageenan-induced paw edema at 80 mg/kg, po administered 30 mins prior to carrageenan challenge measured at 2 hrs by plethysmometer Rattus norvegicus 43.43 %
Antiinflammatory activity in Sprague-Dawley rat assessed as inhibition of carrageenan-induced paw edema at 80 mg/kg, po administered 30 mins prior to carrageenan challenge measured at 3 hrs by plethysmometer Rattus norvegicus 61.88 %
Inhibition of mouse COX-2 expressed in baculovirus infected Sf21 insect cells assessed as reduction in oxygen consumption using arachidonic acid as substrate incubated for 12 mins followed by substrate addition measured for 2 mins Mus musculus 151.36 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus -0.24 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 7.37 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 2.2 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 4.04 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 6.81 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 9.71 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -3.68 %
Inhibition of human SET7 overexpressed in Escherichia coli BL21 (DE3) cells at 50 uM preincubated for 15 mins followed by addition of SAM as substrate and biotinylated Histone H3 (1-50) peptide measured after 30 mins by AlphaLISA assay relative to control Homo sapiens 23.0 %
Inhibition of human SET7 overexpressed in Escherichia coli BL21 (DE3) cells at 25 uM preincubated for 15 mins followed by addition of SAM as substrate and biotinylated Histone H3 (1-50) peptide measured after 30 mins by AlphaLISA assay relative to control Homo sapiens 29.0 %
Inhibition of human SET7 overexpressed in Escherichia coli BL21 (DE3) cells at 12.5 uM preincubated for 15 mins followed by addition of SAM as substrate and biotinylated Histone H3 (1-50) peptide measured after 30 mins by AlphaLISA assay relative to control Homo sapiens 18.0 %
Inhibition of human recombinant COX2 assessed as reduction in PGH2 formation using arachidonic acid as substrate preincubated for 10 mins measured after substrate addition by microplate reader based enzyme immunoassay Homo sapiens 330.0 nM

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
Czech Republic
Slovakia

Cross References

Resources Reference
ChEBI 6741
ChEMBL CHEMBL599
DrugBank DB00814
DrugCentral 1676
FDA SRS VG2QF83CGL
Human Metabolome Database HMDB0014952
Guide to Pharmacology 7220
KEGG C08169
PDB MXM
PubChem 54677470
SureChEMBL SCHEMBL23589638
ZINC ZINC000013129998
CONTENTS