Icosapent
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Also known as All-cis-fatty acid 20:5 omega-3C20:5 (n-3)EicosapentaenoateEicosapentaenoic acidEicosapentaenoic acid (c20:5 n3)EPA 45GIcosapentoIncromega e 7010srRopufa 70Timnodonic acidSID26754924SID50110832SID26754925Eicosapentanoic acidSID144205544
Summary
Icosapent (CHEMBL460026) is an approved small-molecule antineoplastic agent; indicated across 50 conditions including hypertriglyceridemia and cardiovascular disorder.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- Indications: 50 conditions
- Clinical trials: 25
- Chemistry: 302.5 Da · C20H30O2
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL460026 |
| Name | Icosapent |
| Type | Small molecule |
| Max phase | 3 |
| FDA approved | yes |
| PubChem CID | 446284 |
| ChEBI | CHEBI:28364 |
| Molecular formula | C20H30O2 |
| Molecular weight | 302.5 |
| InChIKey | JAZBEHYOTPTENJ-JLNKQSITSA-N |
SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
IUPAC name: (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
ChEBI definition: An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.
Pharmacological roles (ChEBI): nutraceutical, micronutrient, antineoplastic agent, antidepressant, anticholesteremic drug.
Other ChEBI roles (chemical / environmental): Daphnia galeata metabolite, mouse metabolite, fungal metabolite.
Also known as: All-cis-fatty acid 20:5 omega-3, C20:5 (n-3), Eicosapentaenoate, Eicosapentaenoic acid, Eicosapentaenoic acid (c20:5 n3), EPA 45G, Icosapent, Icosapento, Incromega e 7010sr, Ropufa 70, Timnodonic acid, eicosapentaenoic acid
Patent coverage: 19,675 distinct patent families (60,180 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Broader ChEMBL bioactivity targets: 14 (assay-derived). Sample: 4’-phosphopantetheinyl transferase ffp, Histone-lysine N-methyltransferase 2A, Oxoeicosanoid receptor 1, Aromatase, Retinoic acid receptor RXR-alpha, Coagulation factor VII/tissue factor, Prostaglandin G/H synthase 1, Peroxisome proliferator-activated receptor gamma, Peroxisome proliferator-activated receptor alpha, Adenosine receptor A3.
Bioactivity
ChEMBL activities: 9 potent at pChembl ≥ 5 of 17 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| PPARA | 5.96 | IC50 | 1100 | nM | CHEMBL_ACT_12477759 |
| PPARA | 5.96 | IC50 | 1100 | nM | CHEMBL_ACT_12604665 |
| PPARG | 5.8 | IC50 | 1600 | nM | CHEMBL_ACT_12604649 |
| PPARG | 5.7 | Kd | 2000 | nM | CHEMBL_ACT_10990275 |
| OXER1 | 5.7 | IC50 | 2000 | nM | CHEMBL_ACT_13916571 |
| PPARD | 5.4 | IC50 | 4000 | nM | CHEMBL_ACT_12604633 |
| P79208 | 5.15 | IC50 | 7100 | nM | CHEMBL_ACT_2193521 |
| RXRA | 5.12 | Ki | 7632 | nM | CHEMBL_ACT_19307688 |
| PTGS1 | 5.01 | AC50 | 9841 | nM | CHEMBL_ACT_25206486 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
50 indications (0 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 |
|---|---|---|---|
| hypertriglyceridemia | 3 | MONDO:0005347 | EFO:0004211 |
| cardiovascular disorder | 3 | MONDO:0004995 | EFO:0000319 |
| rheumatoid arthritis | 3 | MONDO:0008383 | EFO:0000685 |
| obesity disorder | 3 | MONDO:0011122 | EFO:0001073 |
| heart failure | 3 | MONDO:0005252 | EFO:0003144 |
| IgA glomerulonephritis | 3 | MONDO:0005342 | EFO:0004194 |
| schizoaffective disorder | 3 | MONDO:0005487 | EFO:0005411 |
| intestinal disorder | 3 | MONDO:0005020 | EFO:0009431 |
| cholestasis | 3 | MONDO:0001751 | MONDO:0001751 |
| major depressive disorder | 3 | MONDO:0002009 | MONDO:0002009 |
| coronary artery disorder | 3 | MONDO:0005010 | EFO:0001645 |
| depressive disorder | 3 | MONDO:0002050 | MONDO:0002050 |
| severe acute respiratory syndrome | 3 | MONDO:0005091 | MONDO:0100096 |
| asthma | 3 | MONDO:0004979 | MONDO:0004979 |
| psychotic disorder | 3 | MONDO:0005485 | EFO:0005407 |
| bipolar disorder | 3 | MONDO:0004985 | MONDO:0004985 |
| prostate adenocarcinoma | 2 | MONDO:0005082 | EFO:0000673 |
| autism spectrum disorder | 2 | MONDO:0005258 | EFO:0003756 |
| epilepsy | 2 | MONDO:0005027 | EFO:0000474 |
| liver disorder | 2 | MONDO:0005154 | EFO:0001421 |
| metabolic dysfunction-associated steatotic liver disease | 2 | MONDO:0013209 | EFO:0003095 |
| chronic kidney disease | 2 | MONDO:0005300 | EFO:0003884 |
| drug dependence | 2 | MONDO:0005303 | EFO:0003890 |
| chronic hepatitis C virus infection | 2 | MONDO:0005354 | EFO:0004220 |
| colorectal adenoma | 2 | MONDO:0005484 | EFO:0005406 |
| male breast carcinoma | 2 | MONDO:0005628 | EFO:0006861 |
| social phobia | 2 | MONDO:0001247 | EFO:1001917 |
| fatty liver disease | 2 | MONDO:0004790 | HP:0001397 |
| breast lobular carcinoma | 2 | MONDO:0000552 | EFO:0008509 |
| ductal breast carcinoma in situ | 2 | MONDO:0005023 | EFO:0000432 |
| breast neoplasm | 2 | MONDO:0021100 | MONDO:0007254 |
| follicular lymphoma | 2 | MONDO:0018906 | MONDO:0018906 |
| multiple sclerosis | 2 | MONDO:0005301 | MONDO:0005301 |
| neoplasm | 2 | MONDO:0005070 | MONDO:0004992 |
| systemic lupus erythematosus | 2 | MONDO:0007915 | MONDO:0007915 |
| colorectal neoplasm | 2 | MONDO:0005335 | MONDO:0005575 |
| leukemia | 1 | MONDO:0005059 | EFO:0000565 |
| plasma cell myeloma | 1 | MONDO:0009693 | EFO:0001378 |
| chronic myeloid leukemia | 1 | MONDO:0011996 | EFO:0000339 |
| eating disorder | 1 | MONDO:0005451 | EFO:0005203 |
| diabetic neuropathy | 1 | MONDO:0006626 | EFO:1000783 |
| kidney disorder | 0 | MONDO:0005240 | EFO:0003086 |
8 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 25.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 11 |
| PHASE3 | 5 |
| PHASE4 | 4 |
| PHASE2 | 2 |
| PHASE1 | 2 |
| PHASE1/PHASE2 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00114595 | PHASE4 | COMPLETED | Ethyl-Eicosapentaenoic Acid and Tardive Dyskinesia |
| NCT00692718 | PHASE4 | UNKNOWN | N-3 Fatty Acids for the Prevention of Atrial Fibrillation in Patients With Acute Heart Failure |
| NCT03781557 | PHASE4 | UNKNOWN | Effects of Omega-3 Fatty Acids Supplement in Cognition of Young Healthy Adults and in Their Reaction Time of Computerized Test After 3 Months of Taking High-concentrated DHA and EPA Fish Softgels |
| NCT03915535 | PHASE4 | TERMINATED | Impact of Fish Oil Monoglycerides on the Modulation of Mitochondrial Functions and Lactate Threshold |
| NCT00031707 | PHASE3 | COMPLETED | Comparison of Megestrol and/or Omega-3 Fatty Acid-Enriched Nutritional Supplement in Treating Patients With Cancer-Related Weight Loss and Lack of Appetite |
| NCT00361374 | PHASE3 | COMPLETED | Safety and Effectiveness of Omega 3-Fatty Acids, EPA Versus DHA, for the Treatment of Major Depression |
| NCT01078909 | PHASE3 | COMPLETED | Dose Response Effects of Marine Omega-3 Fatty Acids on Inflammation |
| NCT03693131 | PHASE3 | COMPLETED | Efficacy of MND-2119 in Participants With Hypertriglyceridemia |
| NCT04221217 | PHASE3 | COMPLETED | Long-term Safety and Efficacy Study of MND-2119 in Patients With Hypertriglyceridemia |
| NCT00167310 | PHASE2 | COMPLETED | Decreasing Risk of Coronary Artery Disease in Schizophrenia by Omega-3 Fatty Acid Supplementation |
| NCT01661764 | PHASE2 | COMPLETED | Fish Oil Supplementation, Nutrigenomics and Colorectal Cancer Prevention |
| NCT04006847 | PHASE1/PHASE2 | TERMINATED | Omega -3 Fatty Acid in Combination With Tyrosine Kinase Inhibitors in Chronic Myeloid Leukemia |
| NCT00014027 | PHASE1 | COMPLETED | Effect of Polyunsaturated Fatty Acids on Cardiovascular and Motor Responses Under Stress |
| NCT02113163 | PHASE1 | COMPLETED | PK Study Comparing Metformin Eicosapentaenoate to a Combined Dose of Metformin Hydrochloride and Ethyl Ester EPA |
| NCT07439744 | Not specified | RECRUITING | NUTRIMOOD-Inflammation and Depressive Comorbidity in Obesity: Modulation by Omega-3 Polyunsaturated Fatty Acids Status |
| NCT07462013 | Not specified | RECRUITING | NUTRIBRAIN: Lifestyle Interventions to Prevent cOgnitive Deficits in Subjects With Depressive Symptoms: From mEchanisms to Clinical pRactice (POWER) |
| NCT00487097 | Not specified | COMPLETED | The Effect of Antioxidants on the Immune Response and Wound Healing in Critically Ill Patients |
| NCT00815685 | Not specified | COMPLETED | A Pilot Study of Eicosapentaenoic Acid (EPA) in Patients With Cancer Cachexia |
| NCT01251887 | Not specified | COMPLETED | Dietary Essential Fatty Acid Regulation of Omega-3 HUFA Metabolism; Satiety and Body Composition |
| NCT01270516 | Not specified | COMPLETED | Effect of EPA and HMB on Strength in ICU Patients |
| NCT01369550 | Not specified | COMPLETED | Efficacy Study of Stearidonic Acid (SDA) Soybean Oil-containing Foods on Red Blood Cell Fatty Acid Content |
| NCT01554462 | Not specified | COMPLETED | The Effects of EPA/DHA Supplementation on Cognitive Control in Children With ADHD |
| NCT02069561 | Not specified | COMPLETED | Effects of Eicosapentaenoic Acid on Subjects at High Risk for Colorectal Cancer |
| NCT02179372 | Not specified | COMPLETED | Eicosapentaenoic Free Fatty Acid and Fecal Calprotectin in Inflammatory Bowel Diseases |
| NCT05591664 | Not specified | UNKNOWN | Eicosapentaenoic Acid Serum Levels in Patients With Gestational Diabetes |
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
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).
Related Atlas pages
- Diseases: hypertriglyceridemia, cardiovascular disorder, rheumatoid arthritis, obesity disorder, heart failure, IgA glomerulonephritis, schizoaffective disorder, intestinal disorder, cholestasis, major depressive disorder, coronary artery disorder, depressive disorder, severe acute respiratory syndrome, asthma, psychotic disorder, bipolar disorder