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Compound Detail

CHEMBL509

MECLOFENAMIC ACID
💊 Approved Drug
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💊 Approved Drug
Cc1ccc(Cl)c(Nc2ccccc2C(=O)O)c1Cl

Basic Information

ChEMBL ID CHEMBL509
Name MECLOFENAMIC ACID
Phase Approved
Structure Type MOL
InChI Key SBDNJUWAMKYJOX-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Acide meclofenamique Acido meclofenamico CI-583 CL-583 INF 4668 INF-4668 Meclofenamate Meclofenamic acid NSC-95309
20
Targets
47
Activities
4
Assay Types
3
PK Parameters
20
Publications
9
Known Names
3
Indications

Molecular Properties

296.1
MW (Da)
4.74
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.86
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1980
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -fenamate
USAN Year 1976

Extended Properties

Molecular Formula C14H11Cl2NO2
MW 296.15
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.98

Indications

Arthralgia Myalgia Rheumatic Diseases

ATC Classification

M01AG04
meclofenamic acid
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M02AA18
meclofenamic acid
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN

Activity Summary

IC50 35 meas. best 7.96
Kd 5 meas. best 6.32
Ki 5 meas. best 6.59
EC50 2 meas. best 6.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 2
CHEMBL230
IC50 7.96 7.1733 11.0 3
Prostaglandin G/H synthase 1
CHEMBL2949
IC50 7.3 7.3 50.0 1
Cyclooxygenase
CHEMBL2095157
IC50 7.0 7.0 100.0 4
Prostaglandin G/H synthase 2
CHEMBL4321
IC50 6.7 6.55 200.0 2
Prostaglandin G/H synthase 1
CHEMBL221
IC50 6.69 6.675 203.0 2
Fatty acid-binding protein, liver
CHEMBL5738
Ki 6.59 6.505 256.0 2
Transthyretin
CHEMBL3194
Kd 6.32 6.32 480.0 1
Transthyretin
CHEMBL3194
IC50 6.3 5.3 504.0 2
Aldo-keto reductase family 1 member C3
CHEMBL4681
IC50 6.29 6.2767 512.0 3
Aldo-keto reductase family 1 member C1
CHEMBL5905
IC50 6.13 5.71 740.0 3
Staphylococcus aureus
CHEMBL352
IC50 6.06 6.06 877.0 1
Nuclear receptor subfamily 4 group A member 2/Retinoic acid receptor RXR-alpha
CHEMBL3885613
EC50 6.05 6.05 900.0 1
Mitogen-activated protein kinase 1
CHEMBL4040
IC50 5.5 5.5 3144.0 1
Nuclear receptor subfamily 4immunitygroup A member 1
CHEMBL1293229
EC50 5.33 5.33 4700.0 1
N6-adenosine-methyltransferase catalytic subunit
CHEMBL4739695
IC50 5.1 5.1 8000.0 1
Alpha-ketoglutarate-dependent dioxygenase FTO
CHEMBL2331065
IC50 5.1 4.9867 7940.0 3
Aldo-keto reductase family 1 member C2
CHEMBL5847
IC50 5.06 5.06 8740.0 2
Fatty acid-binding protein, intestinal
CHEMBL4879
Ki 5.05 5.05 8900.0 1
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL312
IC50 4.62 4.62 24000.0 4
Bile salt export pump
CHEMBL6020
IC50 4.57 4.57 27240.0 1
Replicase polyprotein 1ab
CHEMBL4523582
Ki 4.3 4.3 50000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 28.1 hr -
T1/2 1.5 hr Mus musculus
T1/2 1.5 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 2 IC50 = 11.0 nM 7.96 DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 2 IC50 = 40.0 nM 7.4 Inhibition of the human Prostaglandin G/H synthase 2 was determined by thin-laye... 11844663
Prostaglandin G/H synthase 1 IC50 = 50.0 nM 7.3 Inhibition of the ovine Prostaglandin G/H synthase 1 was determined by thin-laye... 11844663
Cyclooxygenase IC50 = 100.0 nM 7.0 Compound was evaluated for its inhibitory activity against CO(cyclooxygenase) -
Cyclooxygenase IC50 = 100.0 nM 7.0 Compound was evaluated in an intact RBL-1 cell line for inhibition of 5-Cyclooxy... -
Cyclooxygenase IC50 = 100.0 nM 7.0 Inhibition of Prostaglandin G/H synthase mediated PGF2-alpha formation in rat ba... 8515419
Cyclooxygenase IC50 = 100.0 nM 7.0 Inhibition of prostaglandin G/H synthase by measuring the reduction of prostagla... 8478906
Prostaglandin G/H synthase 2 IC50 = 200.0 nM 6.7 Inhibition of the murine wild type Prostaglandin G/H synthase 2 11844663
Prostaglandin G/H synthase 1 IC50 = 203.0 nM 6.69 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 1 IC50 = 220.0 nM 6.66 Inhibition of COX1 (unknown origin) 23454516
Fatty acid-binding protein, liver Ki = 256.0 nM 6.59 Displacement of 1-anilinonaphthalene-8-sulphonic acid from rat recombinant L-FAB... 18533710
Fatty acid-binding protein, liver Ki = 379.0 nM 6.42 Displacement of 1-anilinonaphthalene-8-sulphonic acid from rat recombinant L-FAB... 18533710
Prostaglandin G/H synthase 2 IC50 = 400.0 nM 6.4 Inhibition of the murine Arg120Ala mutant type COX-2 11844663
Transthyretin Kd = 480.0 nM 6.32 Binding affinity to TTR (unknown origin) by isothermal titration calorimetric an... 26214366
Transthyretin IC50 = 504.0 nM 6.3 Fluorescence Polarization Binding Assay: Table 3: The FP assay was then adapted ... -
Aldo-keto reductase family 1 member C3 IC50 = 512.0 nM 6.29 Inhibition of recombinant human AKR1C3 expressed in Escherichia coli BL21 cells ... 30429100
Aldo-keto reductase family 1 member C3 IC50 = 540.0 nM 6.27 Inhibition of human recombinant N-terminal His6-tagged AKR1C3 expressed in Esche... 22877157
Aldo-keto reductase family 1 member C3 IC50 = 540.0 nM 6.27 Inhibition of AKR1C3 (unknown origin) 23454516
Prostaglandin G/H synthase 2 IC50 = 700.0 nM 6.16 Inhibition of COX2 (unknown origin) 23454516
Aldo-keto reductase family 1 member C1 IC50 = 740.0 nM 6.13 Inhibition of recombinant human AKR1C1 expressed in Escherichia coli BL21 cells ... 30429100

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
32940035 10.1021/acs.jmedchem.0c01541 No relevant target 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
36356292 10.1021/acs.jmedchem.2c01168 Replicase polyprotein 1ab 6
36356292 10.1021/acs.jmedchem.2c01168 quadruplex DNA 4
11844663 10.1016/s0960-894x(01)00792-2 Prostaglandin G/H synthase 2 3
8478906 10.1021/jm00060a017 Rattus norvegicus 3
26214366 10.1021/acs.jmedchem.5b00544 Transthyretin 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
36356292 10.1021/acs.jmedchem.2c01168 Replicase polyprotein 1a 2
28625364 10.1016/j.bmcl.2017.05.080 Transthyretin 2
17911242 10.1073/pnas.0708036104 Androgen receptor 2
34792334 10.1021/acs.jmedchem.1c01694 Alpha-ketoglutarate-dependent dioxygenase FTO 2
18533710 10.1021/jm701192w Fatty acid-binding protein, liver 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
36356292 10.1021/acs.jmedchem.2c01168 Unchecked 2
34251209 10.1021/acs.jmedchem.1c00186 ADMET 2

Data from ChEMBL 36 via Core Engine