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Compound Detail

CHEMBL622

ETODOLAC
💊 Approved Drug
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💊 Approved Drug
CCc1cccc2c3c([nH]c12)C(CC)(CC(=O)O)OCC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL622
Name ETODOLAC
Phase Approved
Structure Type MOL
InChI Key NNYBQONXHNTVIJ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

(rs)-etodolic acid AY-24,236 AY-24-236 AY-24236 Ebretin Eccoxolac Edolan Etodolac Etodolaco Etodolic acid Etolyn Etopan xl +12 more
5
Targets
13
Activities
2
Assay Types
11
PK Parameters
20
Publications
24
Known Names
12
Indications
1
Mechanisms

Molecular Properties

287.4
MW (Da)
3.38
ALogP
2
HBA
2
HBD
62.3
PSA (Ų)
0.91
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1991
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -ac
USAN Year 1975

Extended Properties

Molecular Formula C17H21NO3
MW 287.36
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.44

Mechanism of Action

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

Indications

Acute Pain Arthritis, Juvenile Arthritis, Rheumatoid Osteoarthritis Rheumatic Diseases Colorectal Neoplasms Muscular Diseases Pain Sprains and Strains Carcinoma, Hepatocellular Pancreatic Neoplasms Lecithin Cholesterol Acyltransferase Deficiency

ATC Classification

M01AB08
etodolac
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Drug Warnings

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

Activity Summary

IC50 12 meas. best 8.03
Ki 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 8.03 6.2 9.4 3
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 8.03 6.66 9.4 3
Unchecked
CHEMBL612545
 IC50 7.64 6.9125 23.0 4
Cyclooxygenase
CHEMBL2094253
 IC50 7.27 7.27 53.5 1
Solute carrier family 22 member 6
CHEMBL1641347
 IC50 4.3 4.3 50000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.31 mL.min-1.kg-1 Homo sapiens
CL 12.88 uL.min-1.(10^6cells)-1 Homo sapiens
CL - mL.min-1.kg-1 Homo sapiens
CL 0.66 mL.min-1.kg-1 Homo sapiens
CL 5.7 mL.min-1.g-1 Homo sapiens
CL 6.2 mL.min-1.g-1 Homo sapiens
CL - - Homo sapiens
F 80.0 % Homo sapiens
F 80.0 % Homo sapiens
Fu 1.1 - Homo sapiens
Fu - - Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 2 IC50 = 9.4 nM 8.03 Inhibition of COX2 (unknown origin) fluorescence based analysis 38516587
Prostaglandin G/H synthase 1 IC50 = 9.4 nM 8.03 Inhibition of human COX1 38516587
Unchecked IC50 = 23.0 nM 7.64 Inhibitory activity against prostaglandin biosynthesis in stimulated chondrocyte... 3263504
Unchecked IC50 = 23.0 nM 7.64 In vitro inhibition of prostaglandin E2 production in cultured chondrocytes 2527995
Unchecked IC50 = 25.0 nM 7.6 Evaluated in vitro for its ability to inhibit prostaglandin E2 production in cul... 2970548
Cyclooxygenase IC50 = 53.5 nM 7.27 Inhibition of COX (unknown origin) 37148849
Prostaglandin G/H synthase 2 IC50 = 561.0 nM 6.25 DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 2 IC50 = 2000.0 nM 5.7 Inhibition of COX2 in human whole blood assessed as inhibition of TXB2 productio... 18752957
Prostaglandin G/H synthase 1 IC50 = 2649.0 nM 5.58 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 1 IC50 = 10300.0 nM 4.99 Inhibition of COX1 in human whole blood assessed as inhibition of LPS-stimulated... 18752957
Unchecked IC50 = 17000.0 nM 4.77 Inhibition of recombinant Curvularia lunata trihydroxynaphthalene reductase 18482840
Solute carrier family 22 member 6 IC50 = 50000.0 nM 4.3 TP_TRANSPORTER: inhibition of Adefovir uptake in OAT1-expressing CHO cells 10991954

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 227
- 10.5281/zenodo.13943903 ADMET 88
31158845 10.1038/s41586-019-1291-3 ADMET 61
16472241 10.2174/1570163043334794 Hepatotoxicity 18
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
22685216 10.1124/dmd.112.045476 Homo sapiens 5
950647 10.1021/jm00228a010 Rattus norvegicus 4
22685216 10.1124/dmd.112.045476 ADMET 4
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
21601448 10.1016/j.bmcl.2011.04.133 No relevant target 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
3373493 10.1021/jm00401a029 Rattus norvegicus 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
1255663 10.1021/jm00225a010 Rattus norvegicus 3

Data from ChEMBL 36 via Core Engine