Etodolac
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Also known as (rs)-etodolic acidAY-24,236AY-24236EbretinEccoxolacEdolanEtodolacoEtodolic acidEtolynEtopan xlFlancoxLodin xlLodineLodine srLodine xlNapilacNIH-9918NSC-282126Ramodar
Summary
Etodolac (CHEMBL622) is an approved small-molecule non-steroidal anti-inflammatory drug (ATC M01AB08) targeting PTGS2; indicated across 11 conditions including rheumatic disorder and rheumatoid arthritis.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: M01AB08
- Targets: 1 (PTGS2)
- Indications: 11 conditions
- Clinical trials: 13
- Chemistry: 287.35 Da · C17H21NO3
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL622 |
| Name | Etodolac |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 3308 |
| ChEBI | CHEBI:4909 |
| ATC | M01AB08 |
| Molecular formula | C17H21NO3 |
| Molecular weight | 287.35 |
| InChIKey | NNYBQONXHNTVIJ-UHFFFAOYSA-N |
SMILES: CCC1=C2C(=CC=C1)C3=C(N2)C(OCC3)(CC)CC(=O)O
IUPAC name: 2-(1,8-diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)acetic acid
ChEBI definition: A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl moiety. A preferential inhibitor of cyclo-oxygenase 2 and non-steroidal anti-inflammatory, it is used for the treatment of rheumatoid arthritis and osteoarthritis, and for the alleviation of postoperative pain. Administered as the racemate, only the (S)-enantiomer is active.
Pharmacological roles (ChEBI): non-steroidal anti-inflammatory drug, cyclooxygenase 2 inhibitor, non-narcotic analgesic, antipyretic.
Also known as: (rs)-etodolic acid, AY-24,236, AY-24236, Ebretin, Eccoxolac, Edolan, Etodolac, Etodolaco, Etodolic acid, Etolyn, Etopan xl, Flancox
Patent coverage: 14,810 distinct patent families (57,872 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 57,799 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| PTGS2 | COX-2 | Inhibition | 4.28 | 0% | P35354 |
Broader ChEMBL bioactivity targets: 12 (assay-derived). Sample: RecQ-like DNA helicase BLM, Peripheral myelin protein 22, Solute carrier family 22 member 6, Thyrotropin receptor, Cyclooxygenase, Prostaglandin G/H synthase 1, Prostaglandin G/H synthase 2, Polyunsaturated fatty acid lipoxygenase ALOX15, Nuclear factor NF-kappa-B p105 subunit, Cytochrome P450 2C9.
Bioactivity
ChEMBL activities: 11 potent at pChembl ≥ 5 of 23 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| PTGS2 | 8.03 | IC50 | 9.4 | nM | CHEMBL_ACT_25553888 |
| PTGS1 | 8.03 | IC50 | 9.4 | nM | CHEMBL_ACT_25553890 |
| PTGS1 | 7.27 | IC50 | 53.5 | nM | CHEMBL_ACT_25650364 |
| BLM | 6.65 | Potency | 223.9 | nM | CHEMBL_ACT_4745883 |
| BLM | 6.65 | Potency | 223.9 | nM | CHEMBL_ACT_4921780 |
| PTGS2 | 6.25 | IC50 | 561 | nM | CHEMBL_ACT_7671612 |
| PTGS2 | 5.7 | IC50 | 2000 | nM | CHEMBL_ACT_2377340 |
| PTGS1 | 5.58 | IC50 | 2649 | nM | CHEMBL_ACT_7671610 |
| CYP3A4 | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_4949331 |
| CYP3A4 | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_5018210 |
| PTGS1 | 5.42 | AC50 | 3840 | nM | CHEMBL_ACT_25205429 |
Target pathways
Aggregated over 1 target gene(s): PTGS2.
Top Reactome pathways
8 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Synthesis of 15-eicosatetraenoic acid derivatives | 1 | PTGS2 |
| Synthesis of Prostaglandins (PG) and Thromboxanes (TX) | 1 | PTGS2 |
| Interleukin-10 signaling | 1 | PTGS2 |
| Interleukin-4 and Interleukin-13 signaling | 1 | PTGS2 |
| Biosynthesis of DHA-derived SPMs | 1 | PTGS2 |
| Biosynthesis of EPA-derived SPMs | 1 | PTGS2 |
| Biosynthesis of DPAn-3 SPMs | 1 | PTGS2 |
| Biosynthesis of electrophilic ω-3 PUFA oxo-derivatives | 1 | PTGS2 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| prostaglandin biosynthetic process | 1 |
| response to oxidative stress | 1 |
| embryo implantation | 1 |
| regulation of blood pressure | 1 |
| response to nematode | 1 |
| response to selenium ion | 1 |
| positive regulation of vascular endothelial growth factor production | 1 |
| cyclooxygenase pathway | 1 |
| lipoxygenase pathway | 1 |
| positive regulation of prostaglandin biosynthetic process | 1 |
| positive regulation of fever generation | 1 |
| prostaglandin secretion | 1 |
| regulation of cell population proliferation | 1 |
| long-chain fatty acid biosynthetic process | 1 |
| positive regulation of nitric oxide biosynthetic process | 1 |
Indications & clinical
Indications
11 indications (5 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| rheumatic disorder | 4 | MONDO:0005554 | EFO:0005755 |
| rheumatoid arthritis | 4 | MONDO:0008383 | EFO:0000685 |
| juvenile idiopathic arthritis | 4 | MONDO:0011429 | EFO:0002609 |
| osteoarthritis | 4 | MONDO:0005178 | MONDO:0005178 |
| muscle tissue disorder | 3 | MONDO:0003939 | EFO:0002970 |
| colorectal neoplasm | 3 | MONDO:0005335 | EFO:0004142 |
| hepatocellular carcinoma | 2 | MONDO:0007256 | EFO:0000182 |
| pancreatic neoplasm | 2 | MONDO:0021040 | EFO:0003860 |
3 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 13.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 4 |
| PHASE2 | 3 |
| Not specified | 3 |
| PHASE1 | 2 |
| PHASE4 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT02881619 | PHASE4 | COMPLETED | Etodolac and Post-bleaching Sensitivity |
| NCT00888797 | PHASE3 | UNKNOWN | β-adrenergic Blocker and a COX2 Inhibitor for Prevention of Colorectal Cancer Recurrence |
| NCT01118572 | PHASE3 | COMPLETED | A Study to Verify the Efficacy of YM177 (Celecoxib) in Postoperative Pain Patients |
| NCT01198834 | PHASE3 | COMPLETED | MRX-7EAT Etodolac-Lidocaine Topical Patch in the Treatment of Ankle Sprains |
| NCT03127592 | PHASE3 | TERMINATED | Phase III Efficacy and Tolerability Trial of the Fixed Dose Combination of Etodolac 400 mg and Cyclobenzaprine 10 mg Versus Isolated Active Substances in Pain Control After Impacted Third Molar Extraction |
| NCT03919461 | PHASE2 | RECRUITING | Colorectal Metastasis Prevention International Trial 2 |
| NCT06839144 | PHASE2 | RECRUITING | Inhibiting Beta-adrenergic and COX-2 Signaling During the Perioperative Period to Reduce Ovarian Cancer Progression |
| NCT03838029 | PHASE2 | UNKNOWN | Perioperative Intervention to Reduce Metastatic Processes in Pancreatic Cancer Patients Undergoing Curative Surgery |
| NCT01746719 | PHASE1 | COMPLETED | Bioequivalence Study of Etodolac Capsules USP 300 mg Under Fasting Condition |
| NCT01749228 | PHASE1 | COMPLETED | Bioequivalence Study of Etodolac Capsules USP 300 mg Under Fed Condition |
| NCT05429970 | Not specified | RECRUITING | A Study Comparing Perioperative Stress Reduction vs. Standard of Care in Ovarian Cancer (PRESERVE) |
| NCT00502684 | Not specified | UNKNOWN | Perioperative Administration of COX 2 Inhibitors and Beta Blockers to Women Undergoing Breast Cancer Surgery |
| NCT05261971 | Not specified | COMPLETED | Evaluation of the Effects of Treatments Applied to Patients With Facial Myalgia on Occlusion Parameters |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.
Related molecules
Related molecules
Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.
201 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| FIDAXOMICIN | ChEMBL + PubChem | Phase 4 (approved) | PTGS2 |
| 3,3’,4’,5-TETRACHLOROSALICYLANILIDE | ChEMBL | Phase 4 (approved) | PTGS2 |
| ABEMACICLIB | ChEMBL | Phase 4 (approved) | PTGS2 |
| ACALABRUTINIB | ChEMBL | Phase 4 (approved) | PTGS2 |
| ACEMETACIN | ChEMBL | Phase 4 (approved) | PTGS2 |
| ACETOPHENAZINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| ACETYLCYSTEINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| ACRIVASTINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| AMODIAQUINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| AMPHOTERICIN B | ChEMBL | Phase 4 (approved) | PTGS2 |
| AMSACRINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| ANISINDIONE | ChEMBL | Phase 4 (approved) | PTGS2 |
| APOMORPHINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| ARFORMOTEROL | ChEMBL | Phase 4 (approved) | PTGS2 |
| ASPIRIN | ChEMBL | Phase 4 (approved) | PTGS2 |
| BAZEDOXIFENE | ChEMBL | Phase 4 (approved) | PTGS2 |
| BENZQUINAMIDE | ChEMBL | Phase 4 (approved) | PTGS2 |
| BEPRIDIL | ChEMBL | Phase 4 (approved) | PTGS2 |
| BIPERIDEN | ChEMBL | Phase 4 (approved) | PTGS2 |
| BROMFENAC | ChEMBL | Phase 4 (approved) | PTGS2 |
| CALCIPOTRIENE | ChEMBL | Phase 4 (approved) | PTGS2 |
| CALCITRIOL | ChEMBL | Phase 4 (approved) | PTGS2 |
| CANDESARTAN CILEXETIL | ChEMBL | Phase 4 (approved) | PTGS2 |
| CANNABIDIOL | ChEMBL | Phase 4 (approved) | PTGS2 |
| CAPSAICIN | ChEMBL | Phase 4 (approved) | PTGS2 |
| CAPTOPRIL | ChEMBL | Phase 4 (approved) | PTGS2 |
| CARPROFEN | ChEMBL | Phase 4 (approved) | PTGS2 |
| CEFAZOLIN | ChEMBL | Phase 4 (approved) | PTGS2 |
| CEFTIZOXIME | ChEMBL | Phase 4 (approved) | PTGS2 |
| CELECOXIB | ChEMBL | Phase 4 (approved) | PTGS2 |
| CEPHRADINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| CIANIDANOL | ChEMBL | Phase 4 (approved) | PTGS2 |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | PTGS2 |
| CRIZOTINIB | ChEMBL | Phase 4 (approved) | PTGS2 |
| DAUNORUBICIN | ChEMBL | Phase 4 (approved) | PTGS2 |
| DESERPIDINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| DEXIBUPROFEN | ChEMBL | Phase 4 (approved) | PTGS2 |
| DEXKETOPROFEN | ChEMBL | Phase 4 (approved) | PTGS2 |
| DICLOFENAC | ChEMBL | Phase 4 (approved) | PTGS2 |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | PTGS2 |
| DOBUTAMINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| DOXORUBICIN | ChEMBL | Phase 4 (approved) | PTGS2 |
| EPINEPHRINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| ERGOTAMINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| ESFLURBIPROFEN | ChEMBL | Phase 4 (approved) | PTGS2 |
| ETORICOXIB | ChEMBL | Phase 4 (approved) | PTGS2 |
| FLUPIRTINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| FLURBIPROFEN | ChEMBL | Phase 4 (approved) | PTGS2 |
| FLUVASTATIN | ChEMBL | Phase 4 (approved) | PTGS2 |
| FOLIC ACID | ChEMBL | Phase 4 (approved) | PTGS2 |
| GLAFENINE | ChEMBL | Phase 4 (approved) | PTGS2 |
| HALOPERIDOL | ChEMBL | Phase 4 (approved) | PTGS2 |
| HEXACHLOROPHENE | ChEMBL | Phase 4 (approved) | PTGS2 |
| IBUPROFEN | ChEMBL | Phase 4 (approved) | PTGS2 |
| ICOSAPENT ETHYL | ChEMBL | Phase 4 (approved) | PTGS2 |
| INDAPAMIDE | ChEMBL | Phase 4 (approved) | PTGS2 |
| INDOCYANINE GREEN ACID FORM | ChEMBL | Phase 4 (approved) | PTGS2 |
| INDOMETHACIN | ChEMBL | Phase 4 (approved) | PTGS2 |
| IPRONIAZID | ChEMBL | Phase 4 (approved) | PTGS2 |
| ISOCARBOXAZID | ChEMBL | Phase 4 (approved) | PTGS2 |
Related Atlas pages
- Genes: PTGS2
- Diseases: rheumatic disorder, rheumatoid arthritis, juvenile idiopathic arthritis, osteoarthritis, muscle tissue disorder, colorectal neoplasm
- Drugs: Fidaxomicin, 3,3’,4’,5-TETRACHLOROSALICYLANILIDE, Abemaciclib, Acalabrutinib, Acemetacin, Acetophenazine, Acetylcysteine, Acrivastine, Amodiaquine, Amphotericin B, Amsacrine, Anisindione, Apomorphine, Arformoterol, Aspirin, Bazedoxifene, Benzquinamide, Bepridil, Biperiden, Bromfenac, Calcipotriene, Calcitriol, Candesartan Cilexetil, Cannabidiol, Capsaicin, Captopril, Carprofen, Cefazolin, Ceftizoxime, Celecoxib, Cephradine, Cianidanol, Clotrimazole, Crizotinib, Daunorubicin, Deserpidine, Dexibuprofen, Dexketoprofen, Diclofenac, Diethylstilbestrol, Dobutamine, Doxorubicin, Epinephrine, Ergotamine, Esflurbiprofen, Etoricoxib, Flupirtine, Flurbiprofen, Fluvastatin, Folic Acid, Glafenine, Haloperidol, Hexachlorophene, Ibuprofen, Icosapent Ethyl, Indapamide, Indocyanine Green Acid Form, Indomethacin, Iproniazid, Isocarboxazid