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Compound Detail

CHEMBL599

MELOXICAM
💊 Approved Drug
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💊 Approved Drug
Cc1cnc(NC(=O)C2=C(O)c3ccccc3S(=O)(=O)N2C)s1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL599
Name MELOXICAM
Phase Approved
Structure Type MOL
InChI Key ZRVUJXDFFKFLMG-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Acticam Anjeso Contacera Coxicam Emdocam Flexicam Inflacam Loxicom Loxitab Melfax Melosus Melovem +18 more
6
Targets
27
Activities
1
Assay Types
14
PK Parameters
20
Publications
30
Known Names
17
Indications
1
Mechanisms

Molecular Properties

351.4
MW (Da)
1.95
ALogP
6
HBA
2
HBD
99.6
PSA (Ų)
0.86
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2000
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -icam
USAN Year 1997

Extended Properties

Molecular Formula C14H13N3O4S2
MW 351.41
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -1.58

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cyclooxygenase-2 inhibitor INHIBITOR Prostaglandin G/H synthase 2 ✓ ✓

Indications

Arthritis, Juvenile Arthritis, Rheumatoid Osteoarthritis Rheumatic Diseases Low Back Pain Migraine Disorders Pain Prostatic Neoplasms Shoulder Pain Spondylitis, Ankylosing Tuberculosis Dysmenorrhea Osteoarthritis, Knee Pharyngitis Pregnancy Toothache Lupus Erythematosus, Systemic

ATC Classification

M01AC06
meloxicam
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M01AC56
meloxicam, combinations
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Drug Warnings

Black Box Warning
gastrointestinal toxicity
Country: United States
Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
neurotoxicity
Country: United States

Activity Summary

IC50 27 meas. best 6.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 2
CHEMBL4321
 IC50 6.82 6.82 151.4 1
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 6.8 5.7755 160.0 11
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 6.0 5.355 1000.0 2
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 5.88 4.8178 1319.0 9
Prostaglandin G/H synthase 2
CHEMBL4102
 IC50 5.86 5.86 1370.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.11 4.11 77500.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 32400.0 ng.hr.mL-1 Homo sapiens
CL 0.12 mL.min-1.kg-1 Homo sapiens
CL 0.1 mL.min-1.kg-1 Homo sapiens
CL 0.12 mL.min-1.kg-1 Homo sapiens
CL 0.12 mL.min-1.kg-1 Homo sapiens
Cmax 3557.1 nM Homo sapiens
F 89.0 % Homo sapiens
Fu 0.003 - Homo sapiens
Fu 0.003 - Homo sapiens
Fu 0.0018 - Homo sapiens
MRT 21.0 hr Homo sapiens
T1/2 18.0 hr Homo sapiens
T1/2 17.4 hr Homo sapiens
Tmax 4.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 2 IC50 = 151.36 nM 6.82 Inhibition of mouse COX-2 expressed in baculovirus infected Sf21 insect cells as... 27842798
Prostaglandin G/H synthase 2 IC50 = 160.0 nM 6.8 Concentration that caused a 50% decrease in the maximal inhibition of Prostaglan... 9871731
Prostaglandin G/H synthase 2 IC50 = 330.0 nM 6.48 Inhibition of human recombinant COX2 assessed as reduction in PGH2 formation usi... 32354672
Prostaglandin G/H synthase 2 IC50 = 490.0 nM 6.31 Concentration of drug that causes a 50% decrease in the maximal inhibition of Pr... 9083488
Prostaglandin G/H synthase 2 IC50 = 490.0 nM 6.31 Inhibition of COX-2 (unknown origin) 37148849
Prostaglandin G/H synthase 2 IC50 = 490.0 nM 6.31 Inhibition of COX-2 (unknown origin) assessed as reduction in PGE2 production 36758304
Prostaglandin G/H synthase 2 IC50 = 700.0 nM 6.16 In vitro inhibitory activity against human whole blood Prostaglandin G/H synthas... 10406640
Prostaglandin G/H synthase 2 IC50 = 938.0 nM 6.03 DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 1 IC50 = 1000.0 nM 6.0 Inhibition of sheep seminal vesicle COX-1 assessed as reduction in oxygen consum... 27842798
Prostaglandin G/H synthase 1 IC50 = 1319.0 nM 5.88 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 2 IC50 = 1370.0 nM 5.86 Inhibition of ovine COX2 after 5 mins by enzyme immuno assay -
Prostaglandin G/H synthase 1 IC50 = 1400.0 nM 5.85 In vitro for its inhibitory activity against human whole blood Prostaglandin G/H... 10406640
Prostaglandin G/H synthase 1 IC50 = 2200.0 nM 5.66 Concentration that caused a 50% decrease in the maximal inhibition of Prostaglan... 9871731
Prostaglandin G/H synthase 2 IC50 = 2400.0 nM 5.62 Inhibition of human COX-2 using arachidonic acid as substrate preincubated for 5... 35685617
Prostaglandin G/H synthase 2 IC50 = 7580.0 nM 5.12 Inhibition of COX-2 (unknown origin) incubated for 5 to 10 mins by fluorometric ... 36696764
Prostaglandin G/H synthase 1 IC50 = 19400.0 nM 4.71 Inhibition of ovine COX1 after 5 mins by enzyme immuno assay -
Prostaglandin G/H synthase 1 IC50 = 31200.0 nM 4.51 Inhibition of human recombinant COX1 assessed as reduction in PGF2alpha formatio... 32354672
Prostaglandin G/H synthase 1 IC50 = 36600.0 nM 4.44 Concentration of drug that causes a 50% decrease in the maximal inhibition of Pr... 9083488
Prostaglandin G/H synthase 1 IC50 = 36600.0 nM 4.44 Inhibition of COX-1 (unknown origin) 37148849
Prostaglandin G/H synthase 1 IC50 = 36600.0 nM 4.44 Inhibition of COX-1 (unknown origin) assessed as reduction in PGE2 production 36758304

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1370
- 10.6019/CHEMBL3885881 Rattus norvegicus 579
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
19015346 10.1128/aac.00530-08 Homo sapiens 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
25740159 10.1016/j.bmcl.2015.02.013 No relevant target 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
33676335 10.1016/j.bmc.2021.116091 ADMET 6
38747896 10.1021/acs.jmedchem.4c00596 No relevant target 5
- 10.1039/C4MD00392F Rattus norvegicus 5
9083488 10.1021/jm9607010 Prostaglandin G/H synthase 2 5
9083488 10.1021/jm9607010 Prostaglandin G/H synthase 1 5
32354672 10.1016/j.bmc.2020.115526 RAW264.7 4
16019946 10.1080/00498250400028197 ADMET 4
18426954 10.1124/dmd.108.020479 ADMET 4
19015346 10.1128/aac.00530-08 Plasma 4
31995375 10.1021/acs.jmedchem.0c00046 Albumin 4
21163557 10.1016/j.ejmech.2010.11.032 Rattus norvegicus 4
9871731 10.1016/s0960-894x(98)00184-x Prostaglandin G/H synthase 1 4

Data from ChEMBL 36 via Core Engine