EPA

Category: lipid

Aliases: Eicosapentaenoic acid, C20:5n3

Pharmacological Mechanism

C20:5 ω-3 polyunsaturated fatty acid. Substrate for COX/LOX enzymes generating series-3 (less inflammatory) prostaglandins + thromboxanes + series-5 leukotrienes. Direct modulator of inflammatory gene expression via PPAR-α, FFAR4. Cardiovascular + triglyceride-lowering effects.

Half-Life (t½)

PO: 18h

Dosing Guidelines

• PO: Typical 1000 mg (Range: 500–4000 mg)

Target Organ Systems

• cardiovascular
• immune-hematologic

Pathways It Modulates

• Arachidonic acid cascade (inhibitor) — AA-derived eicosanoid output (2-series PG, 4-series LT)
• Atherosclerosis plaque pathology (inhibitor) — plaque inflammation + membrane composition
• BDNF / TrkB neurotrophic signaling (activator) — BDNF (anti-inflammatory)
• Bile acid (activator) — beneficial microbiota composition
• Brown adipose thermogenesis (activator) — BAT biogenesis
• CD4 T-helper differentiation (inhibitor) — Th17 + IL-17 production
• Circadian clock (activator) — peripheral clock
• Essential fatty acid conversion (substrate) — bypasses Δ6 + Δ5 desaturase — preferred for tissue n-3 loading
• Ferroptosis (substrate) — PUFA
• Microbiome short-chain fatty acid signaling (activator) — microbial diversity
• NAFLD / MASH (inhibitor) — hepatic inflammation
• Neuroinflammation (inhibitor) — pro-resolving mediator precursor
• Omega-3 / omega-6 fatty acid elongation (substrate) — omega-3 EPA → resolvins + COX-3 substrate
• PPAR α / γ / δ nuclear receptor signaling (activator) — PPARα (PUFA)
• Unfolded protein response / ER stress (inhibitor) — ER stress (anti-inflammatory)
• Wnt / β-catenin canonical signaling (inhibitor) — Wnt
• Wound healing cascade (activator) — pro-resolving mediator precursor

Chemical Identifiers

• PubChem CID: 446284
• Formula: C20H30O2
• Molecular weight: 302.45 g/mol
• InChIKey: JAZBEHYOTPTENJ-JLNKQSITSA-N
• SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O